新型杯芳烃氮、硫杂衍生物的合成与性能研究
|
摘要
杯芳烃是一类由取代苯酚和甲醛缩合而成的大环化合物，它具有独特的空腔结构和丰富的反应点，可制备具有各种官能团、构象确定、π空腔大小可调的衍生物，在分子识别、模拟酶催化、物质的检测和分离等方面都显示出其作为超分子化学中的一类重要的受体化合物的特殊价值，引起了人们的关注，被誉为继冠醚和环糊精之后的“第三代超分子主体化合物”。本论文从主客体化学识别研究的角度着眼，设计并合成了多种含有氮、硫杂原子官能团的杯[4]芳烃衍生物和硫杂杯[4]芳烃衍生物，并研究了它们的客体识别性能，取得了较有意义的研究结果。
本文首先合成了新型的含酰胺和席夫碱单元的杯[4]芳烃衍生物，研究了它们的阳离子吸附性能，新化合物不仅对软硬金属离子均有较好的萃取性能，而且对Na~+和Ag~+有一定的选择性配合能力。其次，在对叔丁基硫杂杯[4]芳烃的下缘1，3位引入芳醛基，合成了硫杂杯[4]二醛基衍生物，硫杂杯[4]二醛基衍生物与苯胺、水杨酰肼、烟酰肼、异烟酰肼等通过席夫碱缩合反应得到新型硫杂杯[4]氮杂衍生物，产率分别为83％，80％，77％和79％。硫杂杯[4]二醛基衍生物与邻苯二胺、乙二酰肼、丙二酰肼、己二酰肼等通过“1+1”分子间缩合得到新型1，3-桥联硫杂杯[4]氮杂衍生物，产率分别为53％，51％，59％和66％。新化合物的结构经IR，~1H NMR，MS和元素分析等证实。最后，本文还首次合成了由杯[4]芳烃和硫杂杯[4]芳烃组成的双杯[4]芳烃，研究发现这种化合物对金属离子和氨基酸都有较好的配合能力。
Calixarenes are macrocylic compounds generally formed by condensation of aldehydesand substituted phenols. Because calixarenes have a calix-shaped, hydrophobic cavity andseveral reactable positions, they have attracted considerable attentions. They are broadlyused as building blocks to construct well preorganized host molecules which have widelyapplying potential in the field of molecular recognition, enzyme mimics, etc. So they areconsidered as the third host molecule after crown ethers and cyclodextrins insupramolecular chemistry. In this thesis, the novel thiacalix[4]arene - based polymers andcalix[4]-aza, thio-crowns were designed, synthesized and their complexation propertieswere studied. Some meaningful results were obtained.
Firstly, a series of new calix[4]arene derivatives were synthesized. It was found thatthey not only possessed good complexation properties for both soft and hard cations, butalso exhibited good complexation selectivity for Na~+and Ag~+. Secondly, thiacalix[4]arenebi-benzaldehyde derivative was synthesized by introducing benzaldehyde groups on1,3-position of p-tert-butylthiacalix[4]arene. Reacting compound with aniline, salicylichydrazide, nicotinic hydrazide or isonicotinic hydrazide gave series of novelthiacalix[4]arene aza derivatives by the Schiff-base condensation in the yields of 83%,80%, 77% and 79%, respectively. Treatment compound with o-phenylendiamine, oxalyldihydrazide, malonic dihydrazide and adipie dihydrazide, afforded novel bridgedthiacalix[4]arene aza derivatives by "1+1" condensation in the yields of 53%, 51%, 59%and 66%. The structures of all new compounds were characterized by IR, ESI-MS, ~1HNMR spectra and elemental analyses. At last, the first example of bisealixarene composedof calix[4]arene and thiacalix[4]arene subunits was facilely synthesized and showed goodcomplexation properties for metal cations and zwitterionieα-amino acids.
本文首先合成了新型的含酰胺和席夫碱单元的杯[4]芳烃衍生物，研究了它们的阳离子吸附性能，新化合物不仅对软硬金属离子均有较好的萃取性能，而且对Na~+和Ag~+有一定的选择性配合能力。其次，在对叔丁基硫杂杯[4]芳烃的下缘1，3位引入芳醛基，合成了硫杂杯[4]二醛基衍生物，硫杂杯[4]二醛基衍生物与苯胺、水杨酰肼、烟酰肼、异烟酰肼等通过席夫碱缩合反应得到新型硫杂杯[4]氮杂衍生物，产率分别为83％，80％，77％和79％。硫杂杯[4]二醛基衍生物与邻苯二胺、乙二酰肼、丙二酰肼、己二酰肼等通过“1+1”分子间缩合得到新型1，3-桥联硫杂杯[4]氮杂衍生物，产率分别为53％，51％，59％和66％。新化合物的结构经IR，~1H NMR，MS和元素分析等证实。最后，本文还首次合成了由杯[4]芳烃和硫杂杯[4]芳烃组成的双杯[4]芳烃，研究发现这种化合物对金属离子和氨基酸都有较好的配合能力。
Calixarenes are macrocylic compounds generally formed by condensation of aldehydesand substituted phenols. Because calixarenes have a calix-shaped, hydrophobic cavity andseveral reactable positions, they have attracted considerable attentions. They are broadlyused as building blocks to construct well preorganized host molecules which have widelyapplying potential in the field of molecular recognition, enzyme mimics, etc. So they areconsidered as the third host molecule after crown ethers and cyclodextrins insupramolecular chemistry. In this thesis, the novel thiacalix[4]arene - based polymers andcalix[4]-aza, thio-crowns were designed, synthesized and their complexation propertieswere studied. Some meaningful results were obtained.
Firstly, a series of new calix[4]arene derivatives were synthesized. It was found thatthey not only possessed good complexation properties for both soft and hard cations, butalso exhibited good complexation selectivity for Na~+and Ag~+. Secondly, thiacalix[4]arenebi-benzaldehyde derivative was synthesized by introducing benzaldehyde groups on1,3-position of p-tert-butylthiacalix[4]arene. Reacting compound with aniline, salicylichydrazide, nicotinic hydrazide or isonicotinic hydrazide gave series of novelthiacalix[4]arene aza derivatives by the Schiff-base condensation in the yields of 83%,80%, 77% and 79%, respectively. Treatment compound with o-phenylendiamine, oxalyldihydrazide, malonic dihydrazide and adipie dihydrazide, afforded novel bridgedthiacalix[4]arene aza derivatives by "1+1" condensation in the yields of 53%, 51%, 59%and 66%. The structures of all new compounds were characterized by IR, ESI-MS, ~1HNMR spectra and elemental analyses. At last, the first example of bisealixarene composedof calix[4]arene and thiacalix[4]arene subunits was facilely synthesized and showed goodcomplexation properties for metal cations and zwitterionieα-amino acids.
引文
1. Casnati A, Sansone F, Ungaro R. Peptido and glycocalixarenes: playing with hydrogen bonds around hydrophobic cavities [J], Ace. Chem. Res, 2003, 36:246-254
2．郑炎松等．杯芳烃的配位性质[J]，化学进展，1999，11：275-285
3．李来生，达世禄，冯钰琦．杯芳烃在液相色谱、毛细管电泳和电色谱中的应用进展[J]，化学进展，2005，17(3)：523-530
4. Dieleman C, Steyer S, Jeunesse C. et al. Diphosphine based on an inherently chiral calix[4]arene scaffold: synthesis and use in enantioseleetive catalysis[J], J. Chem. Soc. Dalton Trans., 2001: 2508-2517
5. Huang C. Z, Ahn J, Kwon S. A new chromium(Ⅲ)/p-tert-butylcalix[4]arene/alkylaluminum Catalyst System for the Preparation of Low Molecular Weight Polyethylene[J], Appl Cata A: Gener, 2004, 258:173-181
6. David S, Manuel L, Catherine J. et al. Heck, Suzuki and Kumada-Corriu Cross-coupling Reactions Mediated by Complexes Based on the Upper rim of Diphosphinated Calix[4]arenas[J], J Molecul Cata A: Chem, 2005, 239(1-2): 257-262
7. Zhang L, Zhang Y, Tan H. B, et al.Investigation of Calix[4]arene-porphyrin and its Palladium(Ⅱ) and Zinc(Ⅱ)complexes at Air/Water Interface and in Langmuir-Blodgett Film[J], Thin Solid Films, 2002, 413(1-2): 224-230
8．毛锋旺，胡晓钧，钱洪平，等．杯芳烃衍生物对K~+和电子的耦合液膜传输[J]，物理化学学报，2004，20(10)：1271-1274
9．狄晓威，何锡文，曾宪顺，等．硒功能化杯芳烃载体银离子选择性膜电极的研究[J]，分析化学，2004，32(4)：430-434
10. Baur M, Frank M, Schatz J. et al. Water-soluble calix[n]arenes as Receptor Molecules for Non-polar Substrates and Inverse Phase Transfer catalysts[J], Tetrahedron, 2001, 57(32): 6985-6991
11. Cafeo G, Kohnke F. H, Latorre G. L.Calix[6]pyrrole and hybrid calix[n]furan[m]pyrroles (n+m=6): Syntheses andHost-guestChemistry[J], Chemistry, 2002, 8(14): 3148-3156
12. Sarkar B, Mukhopadhyay P, Bharadwaj P. K. Laterally Non-symmetric Aza-eryptands: Synthesis, Catalysis and Derivatization to new Receptors[J], Coor Chem Rev, 2003, 236(1-2): 1-13.
13．刘育，尤长城，张衡益．超分子化学—合成受体的分子识别与组装[M]，南开大学出版社，2001：26-27
14．余晓冬，吴采樱．杯芳烃的超分子化学[J]，化学通报，1998，(11)：13-18
15. Amaud-Neu F, Schewing-Weill M, Schewing-Weill M. Calixarenes new selective molecular receptors [J], Synthetic Metals, 1997, 90:157-164
16. Comforth J. W, Mogen. Preparation of antituberculous polyoxyethylene ethers of homogeneous structure[J], Tetrahedron, 1973, 29:1659-1662
17. Gutsche C. D, Ramamurthi M. Calixarene analysis of the product mixtures produced by the based-catalyzed condensation of formaldehyde with para-substituted phenols[J], J.Org. Chem, 1978, 43: 4905-4907
18. Casnati A, Della C. N, Sansone F, et al. Enlarging the size ofealix[4]arene-erowns-6 to impmve Cs~+/K~+ selectivity: a theoretical and experimental study[J], Tetrahedron, 2004, 60(36): 7869-7876
19. Tabakci M, Memon S, Yilmaz M, et al. Synthesis and evaluation of extraction ability of ealix[4]-crown-6 cone conformer and its oligomeric analogue[J], Peactive & Functional Polym. , 2004, 58(1): 27-34
20. Narumi F, Hattori T, Matsumura N, et al. Synthesis of an inherently ehiral O-bridged thiacallx[4]crown carboxylic acid and its application to a chiral solvating agent [J], Tetrahedron, 2004, 60(36): 7827-7833
21. Bohmer V. Calixarenes, macrocycles with (almost) unlimited possibilities [J], Angew. Chem., Int. Ed. Engl., 1995, 34:713-745
22. Casnati A, Sansone F, Ungaro R. Peptido and glyeocalixarenes: playing with hydrogen bonds around hydrophobie cavitie[J], Ace. Chem. Res. 2003, 36:246-254
23．吴萍，韩军，戈云，颜朝国．超分子砌块间苯二酚杯芳烃的研究进展[J]．有机化学，2006，26(4)：431-441
24．王腾风，杨石柱．杯芳烃催化剂在有机反应中的应用[J]，化学试剂，2000，22(5)：274-278
25. Gutsche C. D. Cation binding by macrocycles[J], Top Curr. Chem. 1984, 1: 123
26. Gutsche C. D, Nam K. C. Synthesis properties and metal complexation of aminocalixarenes[J], J.Am.Chem.Soc., 1988, 110:6153
27. Shinkai S, Mori S, Tsubrki T. Molecular design of artificial sugar sensing systems[J], Tetrahedron Lett, 1984, 25:5315
28. See K. A, Fronczek F. R, Gutsche C. D, et al. Conversion of 1, 3-alternate to partial cone conformation ofcalixarene[J], J. Org. Chem, 1991, 56:7256-7268
29. Sharma S. K, Gutsche C. D. Upper rim substitution of calix[4]arenes via their upper rim ae dinitro compounds[J], J. Org. Chem., 1999, 64:3507-3512.
30．褚惠虹，王谨，潘志刚，等．硫杂杯芳烃及其衍生物的合成与表征[J]，有机化学2003，23(11)：1255-1259
31. Gutsche C. D, Lin L. G. The synthesis of functionalized ealixarenes[J], Tetrahedron, 1986, 42: 1633-1640
32. Asfari Z, Wenger S, Vicens. Calixcrowns and related moleeules[J], J. Pure Appl. Chem., 1995, 67: 10372-10376
33．鲁礼林．杯[4]芳烃偶氮衍生物合成与性质研究．北京师范大学硕士学位论文，2004：10-11
34. Vazquez M. L, Franco C. M, Cepeda A, Prognon P, Mahuzier G. Liquid chromatographic study of the interaction between aflatoxins and β-eyelodextrin[J], Anal. Chim. Acta, 1992, 269: 239-247
35. Taniguchi H, Nomura E. Catalytic actively of an octopus-type calixarene on the formation of ethers[J], Chem. Lett., 1988, 2:1773-1776
36. Nijienhuis W. F, Vandoom A. R, Reichwein A. M. Urea transport by macrocyclic carriers through a supported liquid membrane[J], J. Am. Chem. Soc., 1991, 113:3607-3608
37. Chang W. H, Cai P. X, Go X. H. Aldehyde-selective polymeric membrane electrodes based on a calix[4]arene-ionophore[J], Analyst, 1994:1853-1857
38. Castellano R. K, Nuckolls C, Rebek J. Transfer of chiral information through molecular assembly[J], J. Am. Chem. Soe., 1999, 121:11156-11163
39. Grootenhuis P. D. J. Complexation of neutral molecules by synthetic hosts[J], J. Am. Chem. Soe. 1990, 112:4165-4169
40. Stewart D.R, Krawiee M. et at Calixarenes [J], J. Am. Chem. Soe., 1995, 117:586-591
41. Hoom W. P, Frank C. J. M, Reinhoudt D. N. The synthesis of sodium and potassium complexes of two calix[4]arene [J], J. Org. Chem, 1996, 61:7180-7186
42. Gutsche C. D, Levine J. A. Calixarenes, royal society of chemistry[J], J. Am. Chem. Sot., 1982, 104:2652-2656
43. Otsuka K, Araki S, Shinkai. et al. Immobilization of the ring inversion motion in calix[6]arene by a cap with C_3-symmetry[J], J. Org. Chem, 1994, 59:1542-1546
44. Stewart D. C, Krawiec M, et al.Conformation Charteristics of Ether and Esters of P-tert-buyl calix [5] arene[J], Am.Chem.Soc., 1995, 117:586-589
45. Cunsolo F, Consoli G. M. L, Neri P, et al.Tetra-O-alkylated calix[8]arenes with C_4 symmetry[J], Tetra Lett, 1996, 37:5797-5801
46．蔡秀琴．新型杯芳烃衍生物及聚合物的研究[J]，福建师范大学硕士学位论文，2005：2-3
47. Gutsche C. D, Dhawan B, No K. H, Muthukrishnan R. The synthesis, characterization, and properties of the calixarenes from p-tert-butylphenol[J], J. Am. Chem. Soc., 1981, 103: 3782-3785
48. Knop A, Bohmer V, Pilato L. A. Phenol-Formaldehyde polymers, in Comprehensive Polymer Science, Pergamon Press plc[J], Vol.5. Step polymerization, 1989:611-647
49. Nakamoto Y, Ishida S. I. Calix[7]arene from 4-tert-butylphenol and formaldehyde[J], Makromol Chem. Rapid Commum. 1982, 3:705-710
50. Dumazet I, Regnouf-de-Vains J. B, Lamartine R. Synthesis and characterization of p-tert-butyl-calix [9, 10, 11 and 12]arenas[J], Synth. Commun, 1997, 27:2547-2551.
51. Hayes B. T, Hunter R. F. Phenol-formaldehyde and alliedresins Ⅵ: Rational synthesis of a cyclic tetranuclear p-cresol novolak[J], J. Appl. Chem., 1958, 8:743-748
52. No K. Facile synthesis of p-phenyl homooxa-calix[4]arenas[J], Bull Korean Chem. Soc. 1999, 20(1): 33-35
53. B6hmer V, Merkel L, Kunz U. Calix[4]arenas with four differently substituted phenolic units[J], J. Org. Chem., 1987, 35:896-899
54. Bohmer V, Jung K, Schoen M. et al. Direct synthesis of calix[4]arenas with two different phenolic units in aliternating order[J], J. Org. Chem. 1992, 57:790-794
55. Gutsche C. D, Pagoria P. F. Functionalized calixarenes: the direct substitution route[J], J. Org. Chem. 1987, 88(7): 106-120
56. Fu D. k, Xu B, Swager T. M. 3-methylcalix[4]arene: a new versatile precursor to inherently chiral calix[4]arene[J], J. Org. Chem. 1996, 61, 802-808
57. Zhong Z. L, Li J. S, Lu X. R, Chert Y. Y. The improvement of the cyclization step in the stepwise synthesis ofcalix[4]arenes[J], Chem. J. Chinese Univ. 1998, 19:83-86
58. Sone T, Ohba Y, Moriya K. et al. Synthesis and properties of sulfur-bridged analogs of p-tert-butylcalix [4]arene[J], Tetrahedron, 1997, 53:10689-10692
59．郑泽宝．杯芳烃衍生物的合成与性质研究[J]，北京师范大学硕士毕业论文2005：61-63
60. Mogck O, Pons M, Bohrner V. et al. NMR studies of the reversible dimerization and guest exchange processes of tetra urea calix[4]arenas using a derivative with lower symmetry[J], J. Am. Chem. Soc., 1997, 16:1581-1585
61. Gutsche C. D, Nam K. C. Synthesis, properties and metal complexation of aminocalixarenes[J], J. Am. Chem. Soc., 1988, 110:6153-6157
62. Casellato U, Tamburini S, Tomasin P.et al. Hetero-dinuclear sodium-lanthanide(Ⅲ) complexes with an asymmetric compartmental macrocycle[J], Chem, Common, 2000, 2:145-146
63. Scheerder J, Engbersen J. F. J, Castnati A. et al. Complexation of halide anions and tricarboxylate anions by neutral urea-derivitized p-tert-butylcalix[6]arene[J], J. Org. Chem, 1995, 60:6448-6452
64. Beer P. D, Gale P. A. Anion precognition and sensing: the state of the art and future perspectives[J], Angew Chem. In.t ED. Eng.1, 2001, 40(3):486-516
65. Beer P D, Drew M. G. B, Gradwell K. Synthesis and anion coordination chemistry of new calix[4]arene pyridinium receptors[J], J. Chem. Soc. Perkin. Trans. 2, 2000, 3:511-519
66. Kumagai H, Hasegawa M, Miyanari S. et al. Facile synthesis of p-tert-butylthiacalix[4]arene by the reaction of p-tert-butylphenol with elemental sulfur in the presence of a baes[J], Tretrahedron Lett., 1997, 39:3971-3975
67. Cobben P. L. H. M, Egberink R. J. M, Bommer J. G. et al. Transduction of selective recognition of heavy-metal ions by chemically modified field-effect transistors[J], J. Am. Chem. Soc, 1992, 114:10573-10577
68. Beer P. D, Gale P. A. Solution and solid-state studies of 3, 4-dichloro-2, 5-diamidopyrroles: formation of an unusual anionic narcissistic dimmer[J], Angew. Chem. Int. Ed. 2001, 40:486-489
69. Toth A, Floriani C, Chiesi-villa A, Guastini C. Dinuclear copper(Ⅰ) benzoate complexes binding isocyanides and azo compounds[J], Inorganic Chemistry, 1987, 26:236-241
70. Floriant C. Transition metal complexes as bifunctional carriers of polar organometallic: their application to large molecule modifications and to hydrocardon activation carbon[J], Pure and applied chemistry, 1998, 28:1376-1381
71. Cameron B. R. Van Veggel F. C. J, Reinhoudt D. N. Transition metal complexes of lower rim 1, 3-diphosphinite and 1, 3-diphosphino calix[4]arenas[J], J. Org. Chem., 1995, 60:2802-2805
72. Hajek F, Graf E, Hosseini M. W.et al. Synthesis and X-ray analysis of unsymmetrical linear koiland baesd on double fusion of two different calix[4]arene by two silicon atoms[J], Tetra Lett., 1997, 38:4555-4559
73. Giannini L, Solari E, et al. Ethylene rearrangements to MC, M=C, and M C functionalities over a tungsten-Oxo surface illustrated by the W(Ⅳ) calix[4]arene fragment[J], J. Am. Chem. Soc., 1998, 35:2825-2830
74．郑浩，董慧敏，张书胜，冶保献．铜离子参与的硫杂杯芳烃朗格缪膜的电化学性质研究[J]，化学通报，2006，69(8)：627-630
75．Iki N，Kabuto C，et al. Synthesis of p-tert-butylthiacalix[4]ar-ene and its inclusion propeny[J]，Tetrahedron, 2000, 56：1437-1443
76．胡晓钧，王丽，任杰，施宪法．硫杂杯芳烃——类新型的分子受体化合物[J]，化学通报，2004，2：90-95
77. Kon N, Iki N. et al. Tuning of the cavity of water-soluble thiacalix[4]arene for the control of inclusion ability toward water-miscible organic molecules, Collection of Czechoslovak Chemical Communications[J], 2004, 69 (5) : 1080-1096
78. Sone T, Ohba Y. et al. Synthesis and properties of sulfur-bridend analogs of p-tert-butylcalix[4]arene [J], Tetrahedron, 1997, 53 (31):10689～10698
79. Iki N, Kumagai H. et al. Fluorescent chemo-sansor for metal cations based on thiacalix[4]arenes modified with dansyl moieties at the lower rim Tetrahedron[J], 2000, 56 (27) : 4659-4666
80. Morohashi N, Iki N, Sugawara A. et al. Selective oxidation of thiacalix[4]arenes to the sulfinyl and sulfonyl counterparts and their complexation abilities toward metal ions as studied by solvent extraction[J], Tetrahedron2001, 57(26): 5557-5563
81. Iki N, Kabuto C. et al. Fluorescent chemo-sensor for metal cations based on thiacalix[4]arenes modified with dansyl moieties at the lower rim Tetrahedron[J], 2000, 56(27): 4659-4666
82. Izatt R. M, Lamb J. D, Hawkins R. T. et al. Selective M~+-H~+ coupled transport of cations through a liquid membrane by macrocyclic calixarene ligands[J], J. Am. Chem. Sot., 1983, 105:1782-1786
83. Casnati A, Bonetti F, Sansone F, et al. Experimental and theoretical evidence of the bidentate binding mode of dichloroacetamido groups at the upper rim of calix[4]arene hydrogen-bonding anion receptors[J], Collection of Czechoslovak Chemical Communications, 2004, 69(5):1063-1079
84. Dondoni A, Marra A, Massi A. Hybrid solution/solid-pase synthesis of oligosaccharides by using trichloroacetyl isocyanate as sequestration-enabling reagent of sugar alcohols[J], Angew Chem. Int. Ed. Engl. 2005, 44(11):1672-1675
85. Liu Y, Wang H, Zhang H. Y, Liang P. A metallo-capped polyrotaxane containing calix[4]arenas and cyclodextrins and its highly selective binding for Ca~(2+)[J], Chem. Commun(Camb), 2004, 21 (20): 2266-2267
86. Jiaxin Hu, Leonard J, Gokel George W. Probing alkali metal-p interactions with the side chain residue of tryptophan[J], Proceedings of the national academy of sciences of the United States of America, 2002, 124(31):9022-9023
87. Uppadine H. U, Drew M. G. B, Beer P. D. Anion selectivity properties of ruthenium(Ⅱ) tris(5, 5-diamide-2, 2bipyridine) receptors dictated by solvent and amide substation[J], J. Chem. Soc. Chem. Commun, 2001, 3:291-292
88. Bohmer V, Brusko V, Rissanen V. Extended calix[8]arenas by sonogashira cross-coupling with ethynyl arenes[J], Synthesis, 2002, 1898-1902
89. Reinhoudt D. N. Molecular systems for the transduction of host-guest complexation reactions into electronic signals[J], IEEE, 1990, 12(4): 131-135
90. Quchi N, Kihara S, Arita Y. et al. Novel modulator for endothelial adhesion molecules: adipocyte-derived plasma protein adiponectin[J], Circulation, 1999, 100(25): 2473-2476
91．陈远荫，陈义坤．杯[4]单硫(硒)杂冠-5的合成及其对金属离子的识别性能[J]，高等学校化学学报，1999，20：1570-1572
92. Hajek F, Graf E, Hosseini M. W. Synthesis of linear koilands obtained by fusion of calix[4]arene derivatives by silicon atoms[J], Tetrahedron Letters, 1996, 37:1401-1405
93. Chawla H. M, Srinivas K. Synthesis of new chromogenic calix[8]arenas as potential reagents for detection of amines[J], J. Chem. Soc. Chem. Commun. 1994. 1(22): 2593-2594
94. Litao Zhang, Godinez L. A, Gokel G. W. et al. Molecular Recognition at an Interface: Binding of Monolayer-Anchored Ferrocenyl Groups by an Amphiohilic Caiixarene Host Angew[J], Chem. Int. Ed. Engl. 1995, 34: 235-237
95. Kojiro Shimojo, Tatsuya Oshima, Masahiro Goto. Calix[6]arene acetic acid extraction behavior and specificity with respect to nucleobases[J], Analytica Chimiea Acta, 2004, 521:16-20
96. Krawinkler K. H, Maier N. M, et aL Novel urea-linked cinehona-calixarene hybrid-type receptors for efficient chromatographic enantiomer separation of carbamate-protected cyclic amino acids[J], Journal of Chromatography A, 2004, 1053: 11-15
97. Sandor Kunsagi-Mate, Kornelia Szabo, Istvan Bitter, et al. Unexpected effect of charge density of the aromatic guests on the stability of calix[6]arene-phenol host-guest complexes[J], J. Phys. Chem. A. 2005, 109(23):5237-5242
98. Scheerder J, Fochi M, Engbersen J. F. J. et al. Urea-derivatized p-tert-butylcalix[4]arenas: neutral ligands for selective anion complexation[J], J. Org. Chem., 1994, 59:7815-7819
99. Tomapatanagen B, Tuntulani T, Chailapakul O. Calix[4]arenas containing ferroeene amide as earboxylate anion receptors and sensors[J], Org. Lett. 2003, 5(9):1539-1542
100. Beer, P. D, Bernhardt P. V. A ferrocene functionalized macrocyclix receptor for cations and anions[J], J. Chem. Soc. Dalton Trans., 2001, 9:1428-1431
101. Rong Gu, Stefaan Depraetere, Jan Kotek, et al. Anion recognition by a-arylazo-N-confused calix[4]pyrroles[J], Organic & Biomolecular Chemistry, 2005, 3:2921-2923
102．黄志镗，郑企雨．杯芳烃化学的研究[J]，有机化学，2001，21(11)：904-913
103. Izatt N. E, Bruening R. L, Krakowiak K. E. et al. Contributions of professor Reed M. Izatt to molecular recognition technology: from laboratory to commercial application[J], Ind. Eng. Chem. Res. 2000, 39, 3405-3411
104. Rouquette L. H, Ungaro R. et al.New Efficient Calixarene Amide Ionophores for the Selective Removal of Strontium Ion from Nuclear Waste: Synthesis, Complexation, and Extraction Properties[J], Journal of the American Chemical Society 2001, 123(49): 12182-12190
105. Vicens J, Bohmer V. Calixarenes: A Versatile Class of Macrocyclie Compounds. Kluwer Academic Publisheers[J], Dordrecht, 1991
106．郑炎松，沈之荃．杯芳烃的催化性质[J]，化学通报，1998，4：27-31
107. Carden D. E, Diamond D, Miller A. J. An improved Na+ selective microelectrode for intracellular measurements in plant cells[J], J. Exp Bot. 2001, 52(359):1353
108. Katherine M, Connor O, Damien W. M. Arrigan, Gyula Svehla. Calixarenes in electroanalysis[J], Electroanalysis, 2005, 7(3):205-215
109. Chan W. H, Shuang S. M, Martin M. F. Choi. Determination of formaldehyde in air by active sampling on 3-methyl-2-benzothiazolinone hydrochloride-coated glass fibre filters[J], Analyst, 2001, 126:720-723
110．冯亚青，周立山，洪学传，等．杯[4]芳烃受阻胺类复合稳定剂在聚丙烯中的抗热氧稳定性能[J]，应用化学，2001，18(1)：618-622
111．陈艳萍．硫杂杯芳烃硝化衍生物的酸碱性研究．同济大学硕士论文．2004：9-10
112. Iki N, Fujimoto T. et al. A new water-soluble host molecule derived from thiacalixarene[J], Chem Lea.. 1998:625-626
113. Iki N, Narumi F, et al. Selective synthesis of three conformational isomers of tetrakis [(ethoxyearbonyl) methoxy] thiaealix[4]arene and their eomplexation properties towards alkali metal ions[J], J.Chem.Soe.Perkin Trans.2, 1998:2745-2750
114. Akdas H, Mislin G. et al. Synthesis and solid state structural analysis of conformers of tetrakis((ethoxycarbonyl)methoxy)tetrathiacalix[4]arene[J], Tetrahedron Lett, 1999, 40:2113-2116
115. Morohashi N, Iki N. et al. Synthesis and structural characterization of a Pd~(2+) complex with p-tent-butylsulfinylcalix[4]arene[J], Chem.Lett, 2001:66-67
116. Iki N, Fujimoto T et al. Almost complete removal of trace amount of halogenated organic compounds in water: an approach by use of a combination of water-soluble thiaealixarene and ion-exchange resins[J], Chem.Lett., 1999:777-778
117. Iki N, Suzuki T, et al. Inclusion behavior of thiacalix[4]arenetetrasulfonate toward water-miscible organic molecules studied by salting-out and X-ray crystallography[J], Organic Letters, 2002, 4(4): 509-512
118. Narumi F, Iki N, et al. Syntheses of ehirally modified thiacalix[4]arenes with enantiomeric amines and their application to ehiral stationary phases for gas chromatography[J], Enantiomer, 2000, 5(1): 83-89
119. Iki N, Narami F, et al. A new chiral stationary phase for gas chromatography by use of a chiral thiacalix[4]arene derivative[J], Chem.Lett, 1998:1065-1066
120. Narita M. Higuchi Y. et al. Metal sensor of water soluble dansyl—modified thiacalix[4]arenas[J], Tetrahedron Lett., 1998, 39:8687-8690
121. Higuchi Y, Narita M, et al. Fluorescent ehemo-sensor for metal cation based on thiacalix[4]arenas modified with dansyl moieties at the lower rim[J], Tetrahedron, 2000, 56: 4659-4666
122. Ali M. B, Bureau C, et al. Comparison of thiacalix[4]arene thin films behavior on different transducers for copper ion detection[J], Materials Science and Engineering. 2000, 7:83-89
123. Ichikawa Y, Hosogi T. et al. Hydrolysis of phosphate diester bonds by lanthanide complexes of water-soluble thiacalix[4]arenetetrasulfonate[J], Kidorui, 2000,36: 286-287(Jpn)
124. Dozol J, Simon N; et al. A Solution for Cesium Removal fromHigh-Salinity Acidic or Alkaline Liquid Waste:The Crown Calix[4]arenes[J], Separation Science and Technology 1999, 34(6): 877-909
125. Ji H.F,dabestani R, Brown.G.M. A supramolecular fluorescent probe, activated by protons to detect cesium and potassium ions, mimics the function of a logic gate[J], J.Am.Chem.Soc. 2000, 122(38): 9306-9307
126. Bohmer V. Calixarenes, Macrocycles with (Almost) Unlimited Possibilities. Angewandte Chemic[J], Angew. Chem., Int. Ed. Engl. 1995, 34, 713
127. Li X, Gibb C. L, Gibb B. C. Supramolecular Chemistry And Self-assembly Special Feature: Adjusting the binding thermodynamics, kinetics, and orientation of guests within large synthetic hydrophobic pockets[J], J. Am. Chem. Soc. 2002, 99 (8): 4857-4862
128. Pfeiffer J, Schurig V. Enantiomer seperation of amino acid derivatives on a new polymeric chiral calix[4]arene stationary phase by capillary chromatography[J]. J.Chromatogr. A, 1999, 840: 145-150
129. Kubo Y, Sumio T, Maruyama S, Ohhara N. et al. Molecular recognition of butylamines by a binaphthyl-derived chomogenic calix[4]crown[J]. J. Chem. Soc. Chem. Commun., 1995: 1727-1728
130. Casnati A, Sansone F, Sartori A, Prodi L, Montalti M, Zaccheroni N, Ugozzoli F, Ungaro R. Eur. A prototype calix[4]arene-based receptor for carbohydrate recognition containing peptide and phosphate binding groups[J], J. Org. Chem. 2003:1476
131. Scheerder J, Casnati A, Ungaro R, Reinhoudt D. N, Engbersen J. F. J. Complexation of halide anions and tricarboxylate anions by neutral urea-derivatized p-tert-butylcalix[6]arenas[J], J. Org. Chem. 1994,59:7815
132. Jian-Quan Liu, Xi-Wen He, et al A mercury ion-selective electrode based on a calixarene derivative containing the thiazole azo group [J],Chem. J. Chin Univ. 2003, 540 111-117
133. Liu Y, Wang H, Wang L. H. et al. Complextion thermodynamics of water-soluble calix[4]arene derivatives with lanthanoid(Ⅲ) nitrates in acidic aqueous solution[J], Thermoehimiea. 2004, 414(1): 65-70
134. Lu K, Zhang H. J, Zhou Z. X. et al. Studies on the synthesis and properties of dihydroxy-di (hydroxyethoxy) calix[4]arene[J], Chinese Universities Chem. J., 2003, 24(2): 278-281
135．杨发福，蔡秀琴，郭红玉，陈希磊．含酰胺和席夫碱单元的杯[4]芳烃衍生物的合成与配合性能[J]，有机化学，2005，25(5)：545-550
136．吕鉴泉，何锡文，陈朗星，赖家平．功能化杯芳烃在识别分析中的研究进展[J]，分析化学，2001，29，11：1336-1340
137. Nam K. C, Kang S. O, Ko S. W. Urea derivatives of p-tert-butylcalix[4]arenes: Anion selective neutral receptors [J].Bull Korean Chem. Soe., 1999, 20:953-956
138．胡旭波，韩鑫鑫，何家骐，等．一种制备带有酯基基团杯[4]芳烃的简便方法[J]，合成化学，2000，8：151-155
139．杨发福，余天祥，杨先金，杯[4]硫脲衍生物的合成及其对阴离子的络合性能[J]，有机化学2002，22(12)：1040-1043
140. Wan B. W, Jin C. M, Guo X, Lu G. Y. Synthesis of sehiff base calix[4]arene crowns [J], Chin Chem Lett 2002, 13: 699-700
141. Iki N, Narumi F. et al. Selective synthesis of three conformational isomers of tetrakis [(ethoxycarbonyl) methoxy]thiacalix[4]arene and their eomplexation properties towards alkali metal ions[J], J.Chem.Soe.Perkin Tram 2, 1998, 12: 2745-2750
142. Micheal H. et al. Stereoseleetive alkylation ofthiacalix[4]arenes[J], Tetrahedron Lett. 2005, 46(3): 461-464
143. Bhalla V, Kumar M, Katagiri H, Hattori H, Miyano S. Synthesis and binding studies of novel bisthiacalix[4]arenes with iimime linkages[J], Tetrahedron Lett. 2005, 46(1): 121-124
144. Desroches C, Parola P, Voeanson F, Perrin M, Lamartine R, Letoffe J, Bouix J. Nitration of thiacalix[4]arene using nitrosium nitrate complexes: synthesis and characterization of tetranitro-, tetraamino-, and tetra(4-pyridylimino)tetrahydroxythiaealix[4]arene[J], New J. Chem. 2002, 26(5), 651-655
145．杨发福，郑林禄，季衍卿，郭红玉，林建荣．含席夫碱和酰胺单元的新型双杯[4]芳烃的合成[J]，有机化学，2006，26(6)：268-270
146. Lhotak P, Shinkai S.Structurally-unusual ealix[4]arene derivatives generated by intra-and intermolecular mcmurry reactions [J], Tetrahedron Lett, 1996, 37 (5) : 645-648
147．褚惠虹，王谨，潘志刚，胡晓钧，顾金英．施宪法．硫杂杯芳烃及其衍生物的合成与表征[J]，有机化学，2003，23(11)，1255-1259
148. Lhotak P, Stibor I. et al. Stereoselective oxidation of thiacalix[4]arenes with the NaNO_3/CF_3COOH system[J], Tetrahedron Lett. 2003, 44(39): 7333-7336
149. Bitter I, Csokai V. An expedient route to p-tert-butylthiacalix[4]arene 1, 3-diethers via Mitsunobu reactions[J], Tetrahedron Lett. 2003, 44(11), 2261-2265
150. Micheal H, Stibor I, Sykora J, Lhotak P. Stereoseleetive alkylation of thiacalix[4]aren[J], Tetrahedron Lett. 2005, 46(3), 461-464
151. Csokai V, Balazsi B, Bitter I. Unprecedented cyclisations of calix[4]arenes under the Mitsunobu protocol. Part 3: Thiaealix[4] crowns versus dimers[J], Tetrahedron 2004, 60(52): 12059-12066
152. Csokai V, Grun A, Bitter I. Unprecedented Cyclizations of Calix[4]arenes with Glycols under the Mitsunobu Protocol, Part 2.～1 O, O-and O, S-Bridged Calixarenes[J], Org. Lett. 2004, 6(4): 477-480
153. Jin Y, Li X, Gong S. L, Chen Y. Y. Synthesis of doubly azacrowned thiacalixarenes[J], Journal of Chemical Research. S, Synopsis, 2005, 4:240-241
154. Cram D. Expert system monitoring and control of a polymer plant[J], J. Angew. Chem. Int. Ed. Engl., 1988, 27:1009-1020
155. Lehn J. N. Supramolecular chemistry-molecular information and the design of supramolecular materials[J], Angew.Chem.Int. Ed. Engl., 1990, 29:1304-1319
156. Bohmer V. Calixarenes, macrocycles with (almost) unlimited possibilities [J]. Angew. Chem, Int. Ed. Engl., 1995, 34:713-745
2．郑炎松等．杯芳烃的配位性质[J]，化学进展，1999，11：275-285
3．李来生，达世禄，冯钰琦．杯芳烃在液相色谱、毛细管电泳和电色谱中的应用进展[J]，化学进展，2005，17(3)：523-530
4. Dieleman C, Steyer S, Jeunesse C. et al. Diphosphine based on an inherently chiral calix[4]arene scaffold: synthesis and use in enantioseleetive catalysis[J], J. Chem. Soc. Dalton Trans., 2001: 2508-2517
5. Huang C. Z, Ahn J, Kwon S. A new chromium(Ⅲ)/p-tert-butylcalix[4]arene/alkylaluminum Catalyst System for the Preparation of Low Molecular Weight Polyethylene[J], Appl Cata A: Gener, 2004, 258:173-181
6. David S, Manuel L, Catherine J. et al. Heck, Suzuki and Kumada-Corriu Cross-coupling Reactions Mediated by Complexes Based on the Upper rim of Diphosphinated Calix[4]arenas[J], J Molecul Cata A: Chem, 2005, 239(1-2): 257-262
7. Zhang L, Zhang Y, Tan H. B, et al.Investigation of Calix[4]arene-porphyrin and its Palladium(Ⅱ) and Zinc(Ⅱ)complexes at Air/Water Interface and in Langmuir-Blodgett Film[J], Thin Solid Films, 2002, 413(1-2): 224-230
8．毛锋旺，胡晓钧，钱洪平，等．杯芳烃衍生物对K~+和电子的耦合液膜传输[J]，物理化学学报，2004，20(10)：1271-1274
9．狄晓威，何锡文，曾宪顺，等．硒功能化杯芳烃载体银离子选择性膜电极的研究[J]，分析化学，2004，32(4)：430-434
10. Baur M, Frank M, Schatz J. et al. Water-soluble calix[n]arenes as Receptor Molecules for Non-polar Substrates and Inverse Phase Transfer catalysts[J], Tetrahedron, 2001, 57(32): 6985-6991
11. Cafeo G, Kohnke F. H, Latorre G. L.Calix[6]pyrrole and hybrid calix[n]furan[m]pyrroles (n+m=6): Syntheses andHost-guestChemistry[J], Chemistry, 2002, 8(14): 3148-3156
12. Sarkar B, Mukhopadhyay P, Bharadwaj P. K. Laterally Non-symmetric Aza-eryptands: Synthesis, Catalysis and Derivatization to new Receptors[J], Coor Chem Rev, 2003, 236(1-2): 1-13.
13．刘育，尤长城，张衡益．超分子化学—合成受体的分子识别与组装[M]，南开大学出版社，2001：26-27
14．余晓冬，吴采樱．杯芳烃的超分子化学[J]，化学通报，1998，(11)：13-18
15. Amaud-Neu F, Schewing-Weill M, Schewing-Weill M. Calixarenes new selective molecular receptors [J], Synthetic Metals, 1997, 90:157-164
16. Comforth J. W, Mogen. Preparation of antituberculous polyoxyethylene ethers of homogeneous structure[J], Tetrahedron, 1973, 29:1659-1662
17. Gutsche C. D, Ramamurthi M. Calixarene analysis of the product mixtures produced by the based-catalyzed condensation of formaldehyde with para-substituted phenols[J], J.Org. Chem, 1978, 43: 4905-4907
18. Casnati A, Della C. N, Sansone F, et al. Enlarging the size ofealix[4]arene-erowns-6 to impmve Cs~+/K~+ selectivity: a theoretical and experimental study[J], Tetrahedron, 2004, 60(36): 7869-7876
19. Tabakci M, Memon S, Yilmaz M, et al. Synthesis and evaluation of extraction ability of ealix[4]-crown-6 cone conformer and its oligomeric analogue[J], Peactive & Functional Polym. , 2004, 58(1): 27-34
20. Narumi F, Hattori T, Matsumura N, et al. Synthesis of an inherently ehiral O-bridged thiacallx[4]crown carboxylic acid and its application to a chiral solvating agent [J], Tetrahedron, 2004, 60(36): 7827-7833
21. Bohmer V. Calixarenes, macrocycles with (almost) unlimited possibilities [J], Angew. Chem., Int. Ed. Engl., 1995, 34:713-745
22. Casnati A, Sansone F, Ungaro R. Peptido and glyeocalixarenes: playing with hydrogen bonds around hydrophobie cavitie[J], Ace. Chem. Res. 2003, 36:246-254
23．吴萍，韩军，戈云，颜朝国．超分子砌块间苯二酚杯芳烃的研究进展[J]．有机化学，2006，26(4)：431-441
24．王腾风，杨石柱．杯芳烃催化剂在有机反应中的应用[J]，化学试剂，2000，22(5)：274-278
25. Gutsche C. D. Cation binding by macrocycles[J], Top Curr. Chem. 1984, 1: 123
26. Gutsche C. D, Nam K. C. Synthesis properties and metal complexation of aminocalixarenes[J], J.Am.Chem.Soc., 1988, 110:6153
27. Shinkai S, Mori S, Tsubrki T. Molecular design of artificial sugar sensing systems[J], Tetrahedron Lett, 1984, 25:5315
28. See K. A, Fronczek F. R, Gutsche C. D, et al. Conversion of 1, 3-alternate to partial cone conformation ofcalixarene[J], J. Org. Chem, 1991, 56:7256-7268
29. Sharma S. K, Gutsche C. D. Upper rim substitution of calix[4]arenes via their upper rim ae dinitro compounds[J], J. Org. Chem., 1999, 64:3507-3512.
30．褚惠虹，王谨，潘志刚，等．硫杂杯芳烃及其衍生物的合成与表征[J]，有机化学2003，23(11)：1255-1259
31. Gutsche C. D, Lin L. G. The synthesis of functionalized ealixarenes[J], Tetrahedron, 1986, 42: 1633-1640
32. Asfari Z, Wenger S, Vicens. Calixcrowns and related moleeules[J], J. Pure Appl. Chem., 1995, 67: 10372-10376
33．鲁礼林．杯[4]芳烃偶氮衍生物合成与性质研究．北京师范大学硕士学位论文，2004：10-11
34. Vazquez M. L, Franco C. M, Cepeda A, Prognon P, Mahuzier G. Liquid chromatographic study of the interaction between aflatoxins and β-eyelodextrin[J], Anal. Chim. Acta, 1992, 269: 239-247
35. Taniguchi H, Nomura E. Catalytic actively of an octopus-type calixarene on the formation of ethers[J], Chem. Lett., 1988, 2:1773-1776
36. Nijienhuis W. F, Vandoom A. R, Reichwein A. M. Urea transport by macrocyclic carriers through a supported liquid membrane[J], J. Am. Chem. Soc., 1991, 113:3607-3608
37. Chang W. H, Cai P. X, Go X. H. Aldehyde-selective polymeric membrane electrodes based on a calix[4]arene-ionophore[J], Analyst, 1994:1853-1857
38. Castellano R. K, Nuckolls C, Rebek J. Transfer of chiral information through molecular assembly[J], J. Am. Chem. Soe., 1999, 121:11156-11163
39. Grootenhuis P. D. J. Complexation of neutral molecules by synthetic hosts[J], J. Am. Chem. Soe. 1990, 112:4165-4169
40. Stewart D.R, Krawiee M. et at Calixarenes [J], J. Am. Chem. Soe., 1995, 117:586-591
41. Hoom W. P, Frank C. J. M, Reinhoudt D. N. The synthesis of sodium and potassium complexes of two calix[4]arene [J], J. Org. Chem, 1996, 61:7180-7186
42. Gutsche C. D, Levine J. A. Calixarenes, royal society of chemistry[J], J. Am. Chem. Sot., 1982, 104:2652-2656
43. Otsuka K, Araki S, Shinkai. et al. Immobilization of the ring inversion motion in calix[6]arene by a cap with C_3-symmetry[J], J. Org. Chem, 1994, 59:1542-1546
44. Stewart D. C, Krawiec M, et al.Conformation Charteristics of Ether and Esters of P-tert-buyl calix [5] arene[J], Am.Chem.Soc., 1995, 117:586-589
45. Cunsolo F, Consoli G. M. L, Neri P, et al.Tetra-O-alkylated calix[8]arenes with C_4 symmetry[J], Tetra Lett, 1996, 37:5797-5801
46．蔡秀琴．新型杯芳烃衍生物及聚合物的研究[J]，福建师范大学硕士学位论文，2005：2-3
47. Gutsche C. D, Dhawan B, No K. H, Muthukrishnan R. The synthesis, characterization, and properties of the calixarenes from p-tert-butylphenol[J], J. Am. Chem. Soc., 1981, 103: 3782-3785
48. Knop A, Bohmer V, Pilato L. A. Phenol-Formaldehyde polymers, in Comprehensive Polymer Science, Pergamon Press plc[J], Vol.5. Step polymerization, 1989:611-647
49. Nakamoto Y, Ishida S. I. Calix[7]arene from 4-tert-butylphenol and formaldehyde[J], Makromol Chem. Rapid Commum. 1982, 3:705-710
50. Dumazet I, Regnouf-de-Vains J. B, Lamartine R. Synthesis and characterization of p-tert-butyl-calix [9, 10, 11 and 12]arenas[J], Synth. Commun, 1997, 27:2547-2551.
51. Hayes B. T, Hunter R. F. Phenol-formaldehyde and alliedresins Ⅵ: Rational synthesis of a cyclic tetranuclear p-cresol novolak[J], J. Appl. Chem., 1958, 8:743-748
52. No K. Facile synthesis of p-phenyl homooxa-calix[4]arenas[J], Bull Korean Chem. Soc. 1999, 20(1): 33-35
53. B6hmer V, Merkel L, Kunz U. Calix[4]arenas with four differently substituted phenolic units[J], J. Org. Chem., 1987, 35:896-899
54. Bohmer V, Jung K, Schoen M. et al. Direct synthesis of calix[4]arenas with two different phenolic units in aliternating order[J], J. Org. Chem. 1992, 57:790-794
55. Gutsche C. D, Pagoria P. F. Functionalized calixarenes: the direct substitution route[J], J. Org. Chem. 1987, 88(7): 106-120
56. Fu D. k, Xu B, Swager T. M. 3-methylcalix[4]arene: a new versatile precursor to inherently chiral calix[4]arene[J], J. Org. Chem. 1996, 61, 802-808
57. Zhong Z. L, Li J. S, Lu X. R, Chert Y. Y. The improvement of the cyclization step in the stepwise synthesis ofcalix[4]arenes[J], Chem. J. Chinese Univ. 1998, 19:83-86
58. Sone T, Ohba Y, Moriya K. et al. Synthesis and properties of sulfur-bridged analogs of p-tert-butylcalix [4]arene[J], Tetrahedron, 1997, 53:10689-10692
59．郑泽宝．杯芳烃衍生物的合成与性质研究[J]，北京师范大学硕士毕业论文2005：61-63
60. Mogck O, Pons M, Bohrner V. et al. NMR studies of the reversible dimerization and guest exchange processes of tetra urea calix[4]arenas using a derivative with lower symmetry[J], J. Am. Chem. Soc., 1997, 16:1581-1585
61. Gutsche C. D, Nam K. C. Synthesis, properties and metal complexation of aminocalixarenes[J], J. Am. Chem. Soc., 1988, 110:6153-6157
62. Casellato U, Tamburini S, Tomasin P.et al. Hetero-dinuclear sodium-lanthanide(Ⅲ) complexes with an asymmetric compartmental macrocycle[J], Chem, Common, 2000, 2:145-146
63. Scheerder J, Engbersen J. F. J, Castnati A. et al. Complexation of halide anions and tricarboxylate anions by neutral urea-derivitized p-tert-butylcalix[6]arene[J], J. Org. Chem, 1995, 60:6448-6452
64. Beer P. D, Gale P. A. Anion precognition and sensing: the state of the art and future perspectives[J], Angew Chem. In.t ED. Eng.1, 2001, 40(3):486-516
65. Beer P D, Drew M. G. B, Gradwell K. Synthesis and anion coordination chemistry of new calix[4]arene pyridinium receptors[J], J. Chem. Soc. Perkin. Trans. 2, 2000, 3:511-519
66. Kumagai H, Hasegawa M, Miyanari S. et al. Facile synthesis of p-tert-butylthiacalix[4]arene by the reaction of p-tert-butylphenol with elemental sulfur in the presence of a baes[J], Tretrahedron Lett., 1997, 39:3971-3975
67. Cobben P. L. H. M, Egberink R. J. M, Bommer J. G. et al. Transduction of selective recognition of heavy-metal ions by chemically modified field-effect transistors[J], J. Am. Chem. Soc, 1992, 114:10573-10577
68. Beer P. D, Gale P. A. Solution and solid-state studies of 3, 4-dichloro-2, 5-diamidopyrroles: formation of an unusual anionic narcissistic dimmer[J], Angew. Chem. Int. Ed. 2001, 40:486-489
69. Toth A, Floriani C, Chiesi-villa A, Guastini C. Dinuclear copper(Ⅰ) benzoate complexes binding isocyanides and azo compounds[J], Inorganic Chemistry, 1987, 26:236-241
70. Floriant C. Transition metal complexes as bifunctional carriers of polar organometallic: their application to large molecule modifications and to hydrocardon activation carbon[J], Pure and applied chemistry, 1998, 28:1376-1381
71. Cameron B. R. Van Veggel F. C. J, Reinhoudt D. N. Transition metal complexes of lower rim 1, 3-diphosphinite and 1, 3-diphosphino calix[4]arenas[J], J. Org. Chem., 1995, 60:2802-2805
72. Hajek F, Graf E, Hosseini M. W.et al. Synthesis and X-ray analysis of unsymmetrical linear koiland baesd on double fusion of two different calix[4]arene by two silicon atoms[J], Tetra Lett., 1997, 38:4555-4559
73. Giannini L, Solari E, et al. Ethylene rearrangements to MC, M=C, and M C functionalities over a tungsten-Oxo surface illustrated by the W(Ⅳ) calix[4]arene fragment[J], J. Am. Chem. Soc., 1998, 35:2825-2830
74．郑浩，董慧敏，张书胜，冶保献．铜离子参与的硫杂杯芳烃朗格缪膜的电化学性质研究[J]，化学通报，2006，69(8)：627-630
75．Iki N，Kabuto C，et al. Synthesis of p-tert-butylthiacalix[4]ar-ene and its inclusion propeny[J]，Tetrahedron, 2000, 56：1437-1443
76．胡晓钧，王丽，任杰，施宪法．硫杂杯芳烃——类新型的分子受体化合物[J]，化学通报，2004，2：90-95
77. Kon N, Iki N. et al. Tuning of the cavity of water-soluble thiacalix[4]arene for the control of inclusion ability toward water-miscible organic molecules, Collection of Czechoslovak Chemical Communications[J], 2004, 69 (5) : 1080-1096
78. Sone T, Ohba Y. et al. Synthesis and properties of sulfur-bridend analogs of p-tert-butylcalix[4]arene [J], Tetrahedron, 1997, 53 (31):10689～10698
79. Iki N, Kumagai H. et al. Fluorescent chemo-sansor for metal cations based on thiacalix[4]arenes modified with dansyl moieties at the lower rim Tetrahedron[J], 2000, 56 (27) : 4659-4666
80. Morohashi N, Iki N, Sugawara A. et al. Selective oxidation of thiacalix[4]arenes to the sulfinyl and sulfonyl counterparts and their complexation abilities toward metal ions as studied by solvent extraction[J], Tetrahedron2001, 57(26): 5557-5563
81. Iki N, Kabuto C. et al. Fluorescent chemo-sensor for metal cations based on thiacalix[4]arenes modified with dansyl moieties at the lower rim Tetrahedron[J], 2000, 56(27): 4659-4666
82. Izatt R. M, Lamb J. D, Hawkins R. T. et al. Selective M~+-H~+ coupled transport of cations through a liquid membrane by macrocyclic calixarene ligands[J], J. Am. Chem. Sot., 1983, 105:1782-1786
83. Casnati A, Bonetti F, Sansone F, et al. Experimental and theoretical evidence of the bidentate binding mode of dichloroacetamido groups at the upper rim of calix[4]arene hydrogen-bonding anion receptors[J], Collection of Czechoslovak Chemical Communications, 2004, 69(5):1063-1079
84. Dondoni A, Marra A, Massi A. Hybrid solution/solid-pase synthesis of oligosaccharides by using trichloroacetyl isocyanate as sequestration-enabling reagent of sugar alcohols[J], Angew Chem. Int. Ed. Engl. 2005, 44(11):1672-1675
85. Liu Y, Wang H, Zhang H. Y, Liang P. A metallo-capped polyrotaxane containing calix[4]arenas and cyclodextrins and its highly selective binding for Ca~(2+)[J], Chem. Commun(Camb), 2004, 21 (20): 2266-2267
86. Jiaxin Hu, Leonard J, Gokel George W. Probing alkali metal-p interactions with the side chain residue of tryptophan[J], Proceedings of the national academy of sciences of the United States of America, 2002, 124(31):9022-9023
87. Uppadine H. U, Drew M. G. B, Beer P. D. Anion selectivity properties of ruthenium(Ⅱ) tris(5, 5-diamide-2, 2bipyridine) receptors dictated by solvent and amide substation[J], J. Chem. Soc. Chem. Commun, 2001, 3:291-292
88. Bohmer V, Brusko V, Rissanen V. Extended calix[8]arenas by sonogashira cross-coupling with ethynyl arenes[J], Synthesis, 2002, 1898-1902
89. Reinhoudt D. N. Molecular systems for the transduction of host-guest complexation reactions into electronic signals[J], IEEE, 1990, 12(4): 131-135
90. Quchi N, Kihara S, Arita Y. et al. Novel modulator for endothelial adhesion molecules: adipocyte-derived plasma protein adiponectin[J], Circulation, 1999, 100(25): 2473-2476
91．陈远荫，陈义坤．杯[4]单硫(硒)杂冠-5的合成及其对金属离子的识别性能[J]，高等学校化学学报，1999，20：1570-1572
92. Hajek F, Graf E, Hosseini M. W. Synthesis of linear koilands obtained by fusion of calix[4]arene derivatives by silicon atoms[J], Tetrahedron Letters, 1996, 37:1401-1405
93. Chawla H. M, Srinivas K. Synthesis of new chromogenic calix[8]arenas as potential reagents for detection of amines[J], J. Chem. Soc. Chem. Commun. 1994. 1(22): 2593-2594
94. Litao Zhang, Godinez L. A, Gokel G. W. et al. Molecular Recognition at an Interface: Binding of Monolayer-Anchored Ferrocenyl Groups by an Amphiohilic Caiixarene Host Angew[J], Chem. Int. Ed. Engl. 1995, 34: 235-237
95. Kojiro Shimojo, Tatsuya Oshima, Masahiro Goto. Calix[6]arene acetic acid extraction behavior and specificity with respect to nucleobases[J], Analytica Chimiea Acta, 2004, 521:16-20
96. Krawinkler K. H, Maier N. M, et aL Novel urea-linked cinehona-calixarene hybrid-type receptors for efficient chromatographic enantiomer separation of carbamate-protected cyclic amino acids[J], Journal of Chromatography A, 2004, 1053: 11-15
97. Sandor Kunsagi-Mate, Kornelia Szabo, Istvan Bitter, et al. Unexpected effect of charge density of the aromatic guests on the stability of calix[6]arene-phenol host-guest complexes[J], J. Phys. Chem. A. 2005, 109(23):5237-5242
98. Scheerder J, Fochi M, Engbersen J. F. J. et al. Urea-derivatized p-tert-butylcalix[4]arenas: neutral ligands for selective anion complexation[J], J. Org. Chem., 1994, 59:7815-7819
99. Tomapatanagen B, Tuntulani T, Chailapakul O. Calix[4]arenas containing ferroeene amide as earboxylate anion receptors and sensors[J], Org. Lett. 2003, 5(9):1539-1542
100. Beer, P. D, Bernhardt P. V. A ferrocene functionalized macrocyclix receptor for cations and anions[J], J. Chem. Soc. Dalton Trans., 2001, 9:1428-1431
101. Rong Gu, Stefaan Depraetere, Jan Kotek, et al. Anion recognition by a-arylazo-N-confused calix[4]pyrroles[J], Organic & Biomolecular Chemistry, 2005, 3:2921-2923
102．黄志镗，郑企雨．杯芳烃化学的研究[J]，有机化学，2001，21(11)：904-913
103. Izatt N. E, Bruening R. L, Krakowiak K. E. et al. Contributions of professor Reed M. Izatt to molecular recognition technology: from laboratory to commercial application[J], Ind. Eng. Chem. Res. 2000, 39, 3405-3411
104. Rouquette L. H, Ungaro R. et al.New Efficient Calixarene Amide Ionophores for the Selective Removal of Strontium Ion from Nuclear Waste: Synthesis, Complexation, and Extraction Properties[J], Journal of the American Chemical Society 2001, 123(49): 12182-12190
105. Vicens J, Bohmer V. Calixarenes: A Versatile Class of Macrocyclie Compounds. Kluwer Academic Publisheers[J], Dordrecht, 1991
106．郑炎松，沈之荃．杯芳烃的催化性质[J]，化学通报，1998，4：27-31
107. Carden D. E, Diamond D, Miller A. J. An improved Na+ selective microelectrode for intracellular measurements in plant cells[J], J. Exp Bot. 2001, 52(359):1353
108. Katherine M, Connor O, Damien W. M. Arrigan, Gyula Svehla. Calixarenes in electroanalysis[J], Electroanalysis, 2005, 7(3):205-215
109. Chan W. H, Shuang S. M, Martin M. F. Choi. Determination of formaldehyde in air by active sampling on 3-methyl-2-benzothiazolinone hydrochloride-coated glass fibre filters[J], Analyst, 2001, 126:720-723
110．冯亚青，周立山，洪学传，等．杯[4]芳烃受阻胺类复合稳定剂在聚丙烯中的抗热氧稳定性能[J]，应用化学，2001，18(1)：618-622
111．陈艳萍．硫杂杯芳烃硝化衍生物的酸碱性研究．同济大学硕士论文．2004：9-10
112. Iki N, Fujimoto T. et al. A new water-soluble host molecule derived from thiacalixarene[J], Chem Lea.. 1998:625-626
113. Iki N, Narumi F, et al. Selective synthesis of three conformational isomers of tetrakis [(ethoxyearbonyl) methoxy] thiaealix[4]arene and their eomplexation properties towards alkali metal ions[J], J.Chem.Soe.Perkin Trans.2, 1998:2745-2750
114. Akdas H, Mislin G. et al. Synthesis and solid state structural analysis of conformers of tetrakis((ethoxycarbonyl)methoxy)tetrathiacalix[4]arene[J], Tetrahedron Lett, 1999, 40:2113-2116
115. Morohashi N, Iki N. et al. Synthesis and structural characterization of a Pd~(2+) complex with p-tent-butylsulfinylcalix[4]arene[J], Chem.Lett, 2001:66-67
116. Iki N, Fujimoto T et al. Almost complete removal of trace amount of halogenated organic compounds in water: an approach by use of a combination of water-soluble thiaealixarene and ion-exchange resins[J], Chem.Lett., 1999:777-778
117. Iki N, Suzuki T, et al. Inclusion behavior of thiacalix[4]arenetetrasulfonate toward water-miscible organic molecules studied by salting-out and X-ray crystallography[J], Organic Letters, 2002, 4(4): 509-512
118. Narumi F, Iki N, et al. Syntheses of ehirally modified thiacalix[4]arenes with enantiomeric amines and their application to ehiral stationary phases for gas chromatography[J], Enantiomer, 2000, 5(1): 83-89
119. Iki N, Narami F, et al. A new chiral stationary phase for gas chromatography by use of a chiral thiacalix[4]arene derivative[J], Chem.Lett, 1998:1065-1066
120. Narita M. Higuchi Y. et al. Metal sensor of water soluble dansyl—modified thiacalix[4]arenas[J], Tetrahedron Lett., 1998, 39:8687-8690
121. Higuchi Y, Narita M, et al. Fluorescent ehemo-sensor for metal cation based on thiacalix[4]arenas modified with dansyl moieties at the lower rim[J], Tetrahedron, 2000, 56: 4659-4666
122. Ali M. B, Bureau C, et al. Comparison of thiacalix[4]arene thin films behavior on different transducers for copper ion detection[J], Materials Science and Engineering. 2000, 7:83-89
123. Ichikawa Y, Hosogi T. et al. Hydrolysis of phosphate diester bonds by lanthanide complexes of water-soluble thiacalix[4]arenetetrasulfonate[J], Kidorui, 2000,36: 286-287(Jpn)
124. Dozol J, Simon N; et al. A Solution for Cesium Removal fromHigh-Salinity Acidic or Alkaline Liquid Waste:The Crown Calix[4]arenes[J], Separation Science and Technology 1999, 34(6): 877-909
125. Ji H.F,dabestani R, Brown.G.M. A supramolecular fluorescent probe, activated by protons to detect cesium and potassium ions, mimics the function of a logic gate[J], J.Am.Chem.Soc. 2000, 122(38): 9306-9307
126. Bohmer V. Calixarenes, Macrocycles with (Almost) Unlimited Possibilities. Angewandte Chemic[J], Angew. Chem., Int. Ed. Engl. 1995, 34, 713
127. Li X, Gibb C. L, Gibb B. C. Supramolecular Chemistry And Self-assembly Special Feature: Adjusting the binding thermodynamics, kinetics, and orientation of guests within large synthetic hydrophobic pockets[J], J. Am. Chem. Soc. 2002, 99 (8): 4857-4862
128. Pfeiffer J, Schurig V. Enantiomer seperation of amino acid derivatives on a new polymeric chiral calix[4]arene stationary phase by capillary chromatography[J]. J.Chromatogr. A, 1999, 840: 145-150
129. Kubo Y, Sumio T, Maruyama S, Ohhara N. et al. Molecular recognition of butylamines by a binaphthyl-derived chomogenic calix[4]crown[J]. J. Chem. Soc. Chem. Commun., 1995: 1727-1728
130. Casnati A, Sansone F, Sartori A, Prodi L, Montalti M, Zaccheroni N, Ugozzoli F, Ungaro R. Eur. A prototype calix[4]arene-based receptor for carbohydrate recognition containing peptide and phosphate binding groups[J], J. Org. Chem. 2003:1476
131. Scheerder J, Casnati A, Ungaro R, Reinhoudt D. N, Engbersen J. F. J. Complexation of halide anions and tricarboxylate anions by neutral urea-derivatized p-tert-butylcalix[6]arenas[J], J. Org. Chem. 1994,59:7815
132. Jian-Quan Liu, Xi-Wen He, et al A mercury ion-selective electrode based on a calixarene derivative containing the thiazole azo group [J],Chem. J. Chin Univ. 2003, 540 111-117
133. Liu Y, Wang H, Wang L. H. et al. Complextion thermodynamics of water-soluble calix[4]arene derivatives with lanthanoid(Ⅲ) nitrates in acidic aqueous solution[J], Thermoehimiea. 2004, 414(1): 65-70
134. Lu K, Zhang H. J, Zhou Z. X. et al. Studies on the synthesis and properties of dihydroxy-di (hydroxyethoxy) calix[4]arene[J], Chinese Universities Chem. J., 2003, 24(2): 278-281
135．杨发福，蔡秀琴，郭红玉，陈希磊．含酰胺和席夫碱单元的杯[4]芳烃衍生物的合成与配合性能[J]，有机化学，2005，25(5)：545-550
136．吕鉴泉，何锡文，陈朗星，赖家平．功能化杯芳烃在识别分析中的研究进展[J]，分析化学，2001，29，11：1336-1340
137. Nam K. C, Kang S. O, Ko S. W. Urea derivatives of p-tert-butylcalix[4]arenes: Anion selective neutral receptors [J].Bull Korean Chem. Soe., 1999, 20:953-956
138．胡旭波，韩鑫鑫，何家骐，等．一种制备带有酯基基团杯[4]芳烃的简便方法[J]，合成化学，2000，8：151-155
139．杨发福，余天祥，杨先金，杯[4]硫脲衍生物的合成及其对阴离子的络合性能[J]，有机化学2002，22(12)：1040-1043
140. Wan B. W, Jin C. M, Guo X, Lu G. Y. Synthesis of sehiff base calix[4]arene crowns [J], Chin Chem Lett 2002, 13: 699-700
141. Iki N, Narumi F. et al. Selective synthesis of three conformational isomers of tetrakis [(ethoxycarbonyl) methoxy]thiacalix[4]arene and their eomplexation properties towards alkali metal ions[J], J.Chem.Soe.Perkin Tram 2, 1998, 12: 2745-2750
142. Micheal H. et al. Stereoseleetive alkylation ofthiacalix[4]arenes[J], Tetrahedron Lett. 2005, 46(3): 461-464
143. Bhalla V, Kumar M, Katagiri H, Hattori H, Miyano S. Synthesis and binding studies of novel bisthiacalix[4]arenes with iimime linkages[J], Tetrahedron Lett. 2005, 46(1): 121-124
144. Desroches C, Parola P, Voeanson F, Perrin M, Lamartine R, Letoffe J, Bouix J. Nitration of thiacalix[4]arene using nitrosium nitrate complexes: synthesis and characterization of tetranitro-, tetraamino-, and tetra(4-pyridylimino)tetrahydroxythiaealix[4]arene[J], New J. Chem. 2002, 26(5), 651-655
145．杨发福，郑林禄，季衍卿，郭红玉，林建荣．含席夫碱和酰胺单元的新型双杯[4]芳烃的合成[J]，有机化学，2006，26(6)：268-270
146. Lhotak P, Shinkai S.Structurally-unusual ealix[4]arene derivatives generated by intra-and intermolecular mcmurry reactions [J], Tetrahedron Lett, 1996, 37 (5) : 645-648
147．褚惠虹，王谨，潘志刚，胡晓钧，顾金英．施宪法．硫杂杯芳烃及其衍生物的合成与表征[J]，有机化学，2003，23(11)，1255-1259
148. Lhotak P, Stibor I. et al. Stereoselective oxidation of thiacalix[4]arenes with the NaNO_3/CF_3COOH system[J], Tetrahedron Lett. 2003, 44(39): 7333-7336
149. Bitter I, Csokai V. An expedient route to p-tert-butylthiacalix[4]arene 1, 3-diethers via Mitsunobu reactions[J], Tetrahedron Lett. 2003, 44(11), 2261-2265
150. Micheal H, Stibor I, Sykora J, Lhotak P. Stereoseleetive alkylation of thiacalix[4]aren[J], Tetrahedron Lett. 2005, 46(3), 461-464
151. Csokai V, Balazsi B, Bitter I. Unprecedented cyclisations of calix[4]arenes under the Mitsunobu protocol. Part 3: Thiaealix[4] crowns versus dimers[J], Tetrahedron 2004, 60(52): 12059-12066
152. Csokai V, Grun A, Bitter I. Unprecedented Cyclizations of Calix[4]arenes with Glycols under the Mitsunobu Protocol, Part 2.～1 O, O-and O, S-Bridged Calixarenes[J], Org. Lett. 2004, 6(4): 477-480
153. Jin Y, Li X, Gong S. L, Chen Y. Y. Synthesis of doubly azacrowned thiacalixarenes[J], Journal of Chemical Research. S, Synopsis, 2005, 4:240-241
154. Cram D. Expert system monitoring and control of a polymer plant[J], J. Angew. Chem. Int. Ed. Engl., 1988, 27:1009-1020
155. Lehn J. N. Supramolecular chemistry-molecular information and the design of supramolecular materials[J], Angew.Chem.Int. Ed. Engl., 1990, 29:1304-1319
156. Bohmer V. Calixarenes, macrocycles with (almost) unlimited possibilities [J]. Angew. Chem, Int. Ed. Engl., 1995, 34:713-745