新型酰胺硫脲基杯芳烃和双杯芳烃的合成与性能研究
|
摘要
杯芳烃是广受瞩目的第三代主体分子,作为平台构筑对客体具有良好识别能力的新型主体分子一直颇受瞩目。其中,含N、S杂原子桥联的杯芳烃的研究近几年受到了人们的广泛关注,是杯芳烃化学新的研究热点。在杯芳烃引入氨基、酰胺基、脲基、硫脲基等,通过它们的协同效应,对客体具有优良的识别能力。本文以对叔丁基杯[4]芳烃为平台,设计并合成了一系列杯[4]芳烃和双杯[4]芳烃酰胺、硫脲、脲基衍生物,并研究了它们对金属阳离子萃取性能和阴离子的配合性能。
首先,我们合成了具有两个酰胺基,四个硫脲基的开链结构的杯[4]芳烃衍生物。通过金属阳离子萃取实验表明,含酰胺基和硫脲基的杯[4]芳烃衍生物对过渡金属有较好的识别性能,远远优于只含有酰胺基的杯芳烃衍生物,同时对Co~(2+)、Cs~+能较好的高效选择性萃取。
其次,设计并合成了新型的N-支套索杯[4]芳烃氮杂冠醚。金属阳离子萃取实验表明,此类含酰胺基和硫脲基的杯[4]芳烃冠醚衍生物3对软金属离子均有较好的识别性能。
再次,设计并合成了哑铃状酰胺基硫脲基双杯[4]冠醚。阳离子萃取实验表明,新化合物3a、3b对过渡金属离子表现出良好的萃取性能,而对碱金属的作用较弱,其中萃取率高的有Pb~(2+)、Ag~+、Ni~(2+),化合物3a对Co~(2+)表现出较好的配合能力和萃取选择性。另外,我们将新化合物配合能力与结构类似的只含酰胺基的杯[4]芳烃衍生物相比,发现新型杯芳烃衍生物对软金属具有更好的配合性能。阴离子配合实验发现,新化合物对所测阴离子具有良好的识别性能,UV-vis光谱法研究了新化合物与~-OOC(CH_2)_4COO~-阴离子识别配合性能并计算出它们的配合常数,结果表明它们对~-OOC(CH_2)_4COO~-有较好的配合作用,主客体分子形成1∶1的配合物。
Calixarene are the third generation of the host molecules, as a building block to construct the novel host molecules with good recognition abilities towards the guests. Recently, people have paid much attention to N, S-bridged calixarenes. Because calixarene derivatives containing amide、thiourea and urea units, through have good recognition abilities towards the guests. Therefore, studies on their derivation and recognition properties are in the ascendant. In this paper, calix[4]arene is used as a building block, and a series of calix[4]arene derivatives containing amide、thiourea and urea units are designed and synthesized, and their binding properties towards metal cations and anion are studied.
Firstly, we synthesized a calix[4]arene derivative with the structure of open-chain containing two amide units and four thiourea units. Metal cation extraction experiments demonstrate that calix[4]arene derivative containing amide and thiourea units shows much better extraction property towards transition metal ions than that of calixarene derivative only containing amide groups, and it exhibits a good extraction selectivity towards Co~(2+), Cs~+.
Secondly, a novel N-calix[4]arene aza-crown ether derivative is synthesized. Metal cation extraction experiments demonstrate that calix[4]arene derivative containing amide and thiourea units shows good extraction property towards soft metal ions.
Thirdly, dumbbell-biscalix[4]arenes aza-crown ether are synthesized. Metal cation extraction experiments demonstrate that the novel compounds show excellent extraction property towards transition metal ions and poor extraction property towards alkali metal, and they exhibit a good extraction selectivity towards Pb~(2+), Ag~+ and Ni~(2+). The compound 3a exhibits a good extraction selectivity towards Co~(2+). It is found that the extraction percentage of these new calix[4]arene derivatives for soft cations are higher than that of calixarene derivative only containing amide gronps.
The anion binding extraction experiments suggest that these derivatives exhibit excellent recognition towards anion. UV-vis is used to study the binding property of novel compounds towards ~-OOC(CH_2)4_COO~- anions, and their binding constants are calculated. The results show that it possesses good complexation abilities towards ~-OOC(CH_2)_4COO~-, and 1:1 complex compound is formed between host and guest molecules.
首先,我们合成了具有两个酰胺基,四个硫脲基的开链结构的杯[4]芳烃衍生物。通过金属阳离子萃取实验表明,含酰胺基和硫脲基的杯[4]芳烃衍生物对过渡金属有较好的识别性能,远远优于只含有酰胺基的杯芳烃衍生物,同时对Co~(2+)、Cs~+能较好的高效选择性萃取。
其次,设计并合成了新型的N-支套索杯[4]芳烃氮杂冠醚。金属阳离子萃取实验表明,此类含酰胺基和硫脲基的杯[4]芳烃冠醚衍生物3对软金属离子均有较好的识别性能。
再次,设计并合成了哑铃状酰胺基硫脲基双杯[4]冠醚。阳离子萃取实验表明,新化合物3a、3b对过渡金属离子表现出良好的萃取性能,而对碱金属的作用较弱,其中萃取率高的有Pb~(2+)、Ag~+、Ni~(2+),化合物3a对Co~(2+)表现出较好的配合能力和萃取选择性。另外,我们将新化合物配合能力与结构类似的只含酰胺基的杯[4]芳烃衍生物相比,发现新型杯芳烃衍生物对软金属具有更好的配合性能。阴离子配合实验发现,新化合物对所测阴离子具有良好的识别性能,UV-vis光谱法研究了新化合物与~-OOC(CH_2)_4COO~-阴离子识别配合性能并计算出它们的配合常数,结果表明它们对~-OOC(CH_2)_4COO~-有较好的配合作用,主客体分子形成1∶1的配合物。
Calixarene are the third generation of the host molecules, as a building block to construct the novel host molecules with good recognition abilities towards the guests. Recently, people have paid much attention to N, S-bridged calixarenes. Because calixarene derivatives containing amide、thiourea and urea units, through have good recognition abilities towards the guests. Therefore, studies on their derivation and recognition properties are in the ascendant. In this paper, calix[4]arene is used as a building block, and a series of calix[4]arene derivatives containing amide、thiourea and urea units are designed and synthesized, and their binding properties towards metal cations and anion are studied.
Firstly, we synthesized a calix[4]arene derivative with the structure of open-chain containing two amide units and four thiourea units. Metal cation extraction experiments demonstrate that calix[4]arene derivative containing amide and thiourea units shows much better extraction property towards transition metal ions than that of calixarene derivative only containing amide groups, and it exhibits a good extraction selectivity towards Co~(2+), Cs~+.
Secondly, a novel N-calix[4]arene aza-crown ether derivative is synthesized. Metal cation extraction experiments demonstrate that calix[4]arene derivative containing amide and thiourea units shows good extraction property towards soft metal ions.
Thirdly, dumbbell-biscalix[4]arenes aza-crown ether are synthesized. Metal cation extraction experiments demonstrate that the novel compounds show excellent extraction property towards transition metal ions and poor extraction property towards alkali metal, and they exhibit a good extraction selectivity towards Pb~(2+), Ag~+ and Ni~(2+). The compound 3a exhibits a good extraction selectivity towards Co~(2+). It is found that the extraction percentage of these new calix[4]arene derivatives for soft cations are higher than that of calixarene derivative only containing amide gronps.
The anion binding extraction experiments suggest that these derivatives exhibit excellent recognition towards anion. UV-vis is used to study the binding property of novel compounds towards ~-OOC(CH_2)4_COO~- anions, and their binding constants are calculated. The results show that it possesses good complexation abilities towards ~-OOC(CH_2)_4COO~-, and 1:1 complex compound is formed between host and guest molecules.
引文
1.Lehn J.M.Supramolecular chenistrygxcope and perspectives:Molecules-Supermolecules -Molecular devices[J].Journal of Imclusion Phenomena and Macrocyclic Chenistry,1998,6(4):351-356.
2.Lehn J.M.Supramolecular chenistry-scope perspectives molecules,supermolecules evices[J].Angew.Chem.Int.Ed.Engl.,1988,27:89-112.
3.Bohmer V.Calixarenes macrocycles with(almost)unlimited possibilities[J].Angew.Chem.Int.Ed.Engl.,1995,34:713-745.
4.Pochini R.,Ungaro R.,"Calixarenes and related hosts"[J].comprehensive supramolecular chemistry,Pergamon Press Oxford,1996,(2):103-105.
5.赵邦屯,张衡益,刘育.基于杯芳烃主体的分子自组装研究进展[J].有机化学,2005,25(8):913-925.
6.Casnati A.,Sansone F.Ungaro R.,Peptido and glycocalixarenes:playing with hydrogen bonds around hydrophobic cavities[J].Acc.Chem.Res.,2003,36:246-254.
7.王春,何锡文.超分子在质量敏感压电化学传感器中的应用[J].分析测试学报,2001,20(1):84-87.
8.张书胜,何新亚.杯芳烃及其衍生物在色谱和毛细管电泳中的应用[J].化学通报,2001,64(4):226-231.
9.Ikeda A.,Shinkai S.Novel Cavity design using calix[n]arene skeletons:toward molecular recognition and metal binding[J].Chem.Rev.,1997,97:1710-1734.
10.郑炎松.杯芳烃的配位性质[J].化学进展,1999,11(3):275-285.
11.Ngah W.,Endud C.S.,Mayanar R.Removal of copper(Ⅱ)ions from aqueous solution onto chitosan and cross-linked chitosan beads[J].Reactive and Functional Polymers,2002,50(2):181-190.
12.王建玲,林琳.杯芳烃固定液分子识别的热力学性质[J].分析测试学报,1998,17(5): 40-43.
13.Baeyer A.Ueber der Verbindungen der Aldehyde Unit den Phenolen and Aromatischen Kohlenwasser Stoffen[J].Chem.Ber,1872,25:1094-1010.
14.Zinke A.,Ziegler E.,Zur Kenntnis des Hartungs-prozesses yon phenol Formaldehyde Harzen[J].Chem.Ber.,1944,77:264-269.
15.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.,1978,43:4905-4910.
16.Molenveld P.,Engbersen J.F.,Reinhoudt D.N.,et al.Dinuclear bisimi-dazolyl-Cu calix[41arenes as metalloenzyme models,synthesis and bifunctional catalysis in phosphate diester transe-sterification[J].J.Org.Chem.,1999,64:6337-6342.
17.Rondelez Y.,Sdndque Q.,Rager,M.et al.Biomimetic copper(1)CO complexes:a structural and dynamic study of a calix[6]arene-based supramolecular system[J].Eur.J.Chem.,2000,6:4218-4223.
18.郭兵,冯亚青等.新型主体分子-杯芳烃研究进展[J],合成化学,2000,8(5):395-398.
19.刘育,尤长城,张衡黼.超分子化学[M].天津:南开大学出版社,2001:333-356.
20.Gutsche C.D.,Dhawan B.,Levine L.A.Calixarens,royal society of chemistry[J].J.Am.Chem.Soc.,1982,104:2652-2655.
21.Knop A.,Bohmer V.,Pilato L.A.Phenol-Formaldehyde polymers[J].Comprehensive Polymer Science,1989(5):611-647.
22.Nakamoto Y.,Ishida S.I.Calix[7]arene from 4-tert-butylphenol and formaldehyde[J].Makromol Chem.Rapid Commun,1982,3:705-710.
23.Dumazet J.B.,Regrnouf-de-Vains R.Lamartime.Sythesis and characterization of p-tert-butyl-cllix[9,10,11 and 12]arenes[J],Synth.Commun,1991,27:2547-2551.
24.Hayes B.T.,Hunter R.F.Phemol-formaldehyde and alliedresins Ⅵ:Rationl synthesis of a cyc -lic tetramuclear p-cresol novolak[J].Appl.Chem.,1958,8:743-748.
25.Facile K.No.Synthesis of p-phenyl homooxa-calix[4]arenes[J].Bull Korean chem.Soc.,1999,20(1):33-35.
26.Bohmer V.,Merkel L.,Kunz U.Calix[4]arenes with four differently substituted phenolic units[J].J.Org.Chem.,1987,35:896-899.
27.Bohmer V.,Jung K.,Schoen M.,etal.Direct symthesis of calix[4]arenes with two different phenolic units in alitermating order[J].J.Org.Chem.,1992,57:790-794.
28.Pagoria P.F.,Gutsche C.D.Functionalized calixarenes:the direct substitution route[J].J.Org.Chem.,1984,88(7):106-120.
29.Fu D.K.,Xu B.,Swager T.M.3-methylcalix[4]arene:a new versalile precursor to inherently chiral calix[4]arene[J],J.Org.Chem.,1996,61:802-808.
30.Zhong Z.L.,Li J.S.,Lu X.R.,et al.The imporovement of the cyclization step in the stepwicse synthesis of calix[4]arenes[J].Chem.Chinese Univ.,1998,19:83-86.
31.Sone T.,Ohba Y.,Oriya K.,et al.Synthesis and properties of sulfur-bridged analogs of p-tert-But-ylclaix[4]arene[J].Tetrahedron,1997,53:10689-10692.
32.Kumagai H.,aseawa M.,iyamari S.,ctal.Facile synethesis 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.
33.Hoorn W.P.,rank C.J.M.,einhoudt D.N.Conformatonal characteristcs of ethers and esters of p-tert-butylcalix[5]arene[J].J.Org.Chem.,1996,61:7180-7184.
34.Levine L.A.,Gutsche C.D.Calixarene,royal society of chemistry[J].J.Am.Chem.Soc.,1982,104:2652-2655.
35.陆国元,陈中俊.杯[4]芳烃衍生物的合成和构象研究[J].高等学校化学学报,1996,17(8):1244-1246.
36.李建森,陈远荫.桥联杯[6]芳烃研究进展[J].有机化学,2000,20(6):841-849.
37.苏晓渝,谢如刚.超分子自组装中的非共价键协同作用[J].化学研究与应用,2007,19(12):1304-1310.
38.钟志梅,姚俊学.杯芳烃及其衍生物的研究进展[J].内蒙古石油化工,2005,31(2):9-11.
39.Bell S.E.J.,Browne V.,McKee M.A.,et al.Structure of p-Phenylcalix[5]arene Dichloroform Solvate[J].J.Chem.Soc.,2005,26(2):337-341.
40.Grote G.M.,Verboom W.,Veggel F.C.,et al.Conformational extremes in the suoramolecular assemblies of para-sjlronato-calix[8]arene[J].J.Chem.Soc.,2006,30:987-990.
41.Rudkevich D.M,Verboom W.Supramolecular Structures fron Lysine Peptides and Carbon Dioxide[J].J.Org.Chem.,2006,71:8696-8705.
42.陈朗星,郭洪声,何锡文.杯芳烃的功能化修饰及其在分子识别中的应用[J].化学进展,2001,13(3):210-215.
43.Mairana D.,Zouhair A.,Natalia K.,et al.Thiacrowncalix[4]arene derivatives:synthesis and complexing properties[J].Super.Chem.,2005,17(3):221-226.
44.Seangpraserkij R.,Asfari Z.,Amaud F.,et al.Schiff base p-tert-butylcalix[4]arenes,synthesis and metal ion complexation[J].J.Org.Chem.,199459:1741-1745.
45.Rudkevich D.M.,Veboom W.,Reinhoudt D.N.Calix[4]arene salenes:A bifunctional receptor for NaH_2PO_4[J].J.Org.Chem.,1994,59:3683-3688.
46.Bohmer V.,Mogck O.,Ports M.,et al.NMR studies of the renersible dimerization and guest exchange processes of tetra urea calix[4]arenes using a derivative with lower syrmetry[J].J.Am.Chem.Soc.,1997,16:1581-1585.
47.Gusche C.D.,Nam K.C.Synthesis,porperties and metal complexation of aminocalixarenes[J].J.Am.Chem.Soc.,1988,110:6153-6157.
48.Casellato U.,Tamburini S.,Tomasin P.,et al.Heero-dinuclear sodium-lanthanide(Ⅲcomplexes with an asymmetric compartmental macrocycle[J].Chem.,Common.,2000,2:145-146.
49.Li X.,Gong S.L.,Zhang C.L.,et al.(1+1)or(2+2)Coupling for bis(tosyloxyethoxy)benanenes with calix[4]arene and thiacalix[4]arene[J].Tetrahedron letters,2006,47:7695-7698.
50.张德华,吕鉴泉.芘冠醚双功能化杯[4]芳烃的合成与表征[J].化学试剂,2006,28(10):627-628,631.
51.王巍,龚淑玲,孟令芝,等.单炔基桥联双杯[4]芳烃的合成与对溶剂分子的包合性能[J].高等学校化学学报,2005,26(8):1467-1470.
52.Castellano R.K.,Nuckolls C.,Rebek J.Transfer of chiral information through molecular assembly[J].J.Am.Chem.Soc.,1999,121:11156-11163.
53.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.
54.Vazquez M.L.,Franco C.M.,Cepeda A.,et al.Liquid chromatographic study of the interaction between aflatoxins and β-cyclodextrin[J].Anal.Chem.Acta.,1992,269:239-247.
55.郑琴,龚淑玲,张春雷,等.双杯芳烃研究进展[J].化学进展,2007,19(5):722-734.
56.Beer P.D.,Keefe A.D.Slawin A.M.Z.,et al.Highly Ordered Smectic Phases from Polar Calix[4]arene Derivatives[J].J.Chem.Soc.Dalton Tram.,1990,(12):3675-3682.
57.Shinkai S.Araki K.,Matsuda T.,et al.NMR and crystallographic studies of p-sulfonatocalix[4]arene-guest complex[J].J.Am.Chem.Soc.,1990,112(25):9053-9058.
58.Santoyo-Gonzalez E,Tortes-Pinedo A.,Barria C.S.Mono-and Dinuclear Oxovanadium (V)calixarene Complexes and Their Activity as Oxidation Catalysts[J].J.Org.Chem.,2000(21):3587-3593.
59.Beer P.D.,Gale P.D.,Hesek D.Synthesis and characterization of chiral catenanes based on rigid calix[4]arene[J].Tetrahedron Lett.,I995,36(5):767-770.
60.杨发福,郑林禄,季衍卿等.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(2):268-270.
61.吉傲,郑炎松,刘劲强,等.含氮杯[4]芳烃的合成[J].化学与生物工程,2007,24(4):44-46.
62.安琳,颜朝国.杯芳烃偶氮类衍生物对金属离子的萃取作用[J].化学研究,2007,18(1):84-85.
63.戈云,吴萍,韩军,等.四-(p羟基苯基)杯[4]间苯二酚芳烃的烃基化和酰胺化反应[J].有机化学,2006,26(5):681-684.
64.肖元晶,吴晓军,曾振亚,等.一类新型四酰胺杯[4]氮杂冠醚的合成及阴离子识别研究[J]. 化学学报,2003,61(12):1986-1990.
65.Ivan I.,Omran A.,Svetlana E.,et al.The synthesis of tetracarbonyl derivatives of thiacalix[4]aren -e in different conformations and their complexation properties towards alkali metal ions[J].Tetrahedron,2003,59:1469-1476.
66.Iki N.,Morohashi N.,Narumi F.,et al.Novel molecular receptors based on a thiacalix[4]arene platform.Preparations of the di-and tetracarboxylic acid derivatives and their binding properties towards transition metal ions[J].Tetrahedron Letters,1999,40:7337-7341.
67.Tastny'V.,Stibor I.,Dvori H.,et al.Synthesis of(thia)calix[4]arene oligomers:towards calixarene-based dendrimers[J].Tetrahedron,2004,60:3383-3391.
68.夏琳,邱桂学.化学科学的研究新领域-超分子化学[J].化学推进剂与高分子材料,2007,5(1):33-37.
69.张穗娟,李琼芳,李如芳.关于超分子化学[J].广东化工,2004,31(6):36-37.
70.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.
71.Chawia H.M.,Srinivas K.Synthesis of new chromogenic calix[8]arenes as potential reagents for detection of amines[J].J.Chem.Soc.,Chem.Comrnun.,1994.1(220):2593-2594.
72.Zhang L,Agodinea L.,LuT.,et al.Preparative Enantiomer Separation of the Anesthetic Enflurane by Gas Inclusion Chromatography[J].Angew.Chem.Int.Ed.Engl.1990,29:939-941.
73.Nakamato Y.,Ishida S.Calix[7]Arene from 4-tert-butylphenol and fromaldehyde[J].Makromol Chem.Rapid Commun.,1982,3:705-707.
74.Barteri M.,Pispisa B.Effeet of pH on thestreospeclfic peroxidatic activity of Chiral association complexes between iron(111)chelate ions and polypeptides[J].MakromoI Chem.Rapid Commun.,1982:715-721.
75.Bott S.G.,Coleman A.W.,Atwood J.L.Intercalation of cationic,anionic and Molecular species by organic hosts.Prevaration and crystal structure of[NH_4]_6[calix[4]arenesulfonate][MeOSO_3].cnt-dot(H_2O)_2[J].J.Am.Chem.Soc.1988,110:610-611.
76.MckerVey M.A.,Seward E.M.,Ferguson G.,et al.Synthesis and x-ray crystal slructure of a calixI4]arene tetracarbonate-acetonitrile(1:1)chathrate[J].J.Org.Chem.1986,51:3581-3584.
77.Rizzoli C.,Andreetti G.D.,Ungaro R.,et al.On the separalion of motions in theory of polyatomic molecularspectra[M].J.Mol.Struct.,1982,87:133-139.
78.Aoyama Y.,Tanaka Y.,Toi H.,et al.Transport from Multiple Alk-ali Cation Mixture Using a Liquid Membrane System Containing a Series of Calixarene Carriers[J].J.Am.Chem.Soc.,1988,1110:634-636.
79.陈再鸿,林俊,郑南峰,等.球烯与对叔丁基杯[8]烃苯醚形成超分子包合物的研究[J].厦门大学学报(自然科学版),1999,38(4):547-551.
80.Atwood J.L.,Kontsantonis G.A.,Raston C.L.Purification of C60 andC70 by selective complexation with calixarenes[J].Nature.,1994,368:229-231.
81.Gutsche C.D,Levine.L.Synthesis of a Functionalizable Calix[4]arene in a Conformationally Rigid Cone Comformation[J].J.Am.Chem.Soc.,1982,104:2652-2655.
82.史春越,曹家庆,范平.杯芳烃对有机小分子识别作用的研究进展[J].辽宁大学学报(自然科学版),2003,30(1):82-86.
83.Zielenkiewicz W.,Mareinowiez A.,Poznanski J.,et al.Compexation of isoleucine by phosphorylated calyx[4]arene in methanol,followed by calorimetry,NMR and UV-VIS spectroscopies and molecular modeling methods[J].Journal of Molecular Liquids,2005,121:8-14.
84.Liu Y.,Ma Y.H.,Chen Y.,et al.Molecular recognition thermodynamics of pyridine derivatives by sulfonatocalixarenes at different pH values[J].J.Org.Chem.,2006,71:6468-6473.
85.韩宝航,刘育,陈荣悌.水溶性杯芳烃对染料客体分子的包结配位作用[J].化学学报,2001,59(4):550-555.
86.Mate S.K.,Szabo K.,Lemli B.,et al.Host-guest interaction between water-soluble calix[6]arene hexasulfonate and p-nitrophenol[J].Thermochimiea Acta,2005,425:121-126.
87.Iwamolto K.,Araki K.,Shimkai S.Conformations and Struerures of Tetra-o-alkylptert-butylca lis[4]arene[J].J.Org.Chem.1991,56:4956-4962.
88.Shinkai S.,Araki K.,Koreishi H.On the Acidity of the Hydroxyl G roup in Calixarenes and the Dissociation-dependent Conformational Change[J].Chem.Lett.,1986,56:1351-1353.
89.Shinkai S.On the Origin of High Ionophricity of 1,3-Alternate Calix[4]arenes[J].J.Am.Chem.Soc.,116:3102-3110.
90.Chawia H.M.,Srimivas K.Syntyesis and Structure of a Capping Calix[6]arenewith 1,2,4,5-etra-kis(bromomethyl)benzene[J].Tetrahedron.1995,51:2709-2711.
91.Doneld B.,Gary D.C.,Domenico C.Asylnmetrically-substituted Calix[4]arene[J].J.Chem.Soc.,chem.commum.,1995:675-678.
92.Loeber C.,Matt D.Alremation Alkylation of p-tert-Calixarene in the Precenee of weak base[J].J.Org.Chem.,1995,60:4126-4128.
93.Chawla H.M.,Srinivas K.Synthesis of new chromogenic calix[8]arenes[J].Tetrahedron Letters.1994,35:2925-2928.
94.陈淑华,李东红.杯芳烃类受体的分子识别作用研究进展[J].有机化学,1999,19(4):339-347.
95.Pudkebich D.,Verhoeven M.,Reinhoudt D.5,9-Methanobenzoannulenam In-es Improved synthesis of 11-amino-5,9-methanobenzo[8]annulenes[J].J.Chem.Soc.Perkin Transl.1995,1:133-140.
96.袁立华,黄枢.靛酚型生色杯[4]芳烃及其与金属离子络合的紫外-可见光谱研究[J].合成化学.1995,3(3):194-197.
97.余天祥,杨先金.杯[4]双硫脲化合物的合成及其对H_2PO_4~-络合作用[J].武汉大学学报:自然科学版,1999,45(6):811-813.
98.Bulgler J.,Hoek A.,et al.Interconnective host-fuest complexation of cyclodextrin-calix[4]arene couples[J].J.Am.Chem.Soc.,1999,121:28-33.
99.Halouani H.,Bonnamour I.D.,Perrin M.,et al.First synthesis and struture of ketoimine calix[4]arene:complexation and extraction studies[J].J.Org.Chem.,2004,69:6521-6527.
100.Metibier R.,Leray I.,Valeur B.Lead and mercury sensing by calixarene based fluoroionophores bearing two or four dansyl fluorophores[J].J.Chem.Eur.,2004,10:4480-4490.
101.Deligue X.Multicavitands Ⅱ:Synthesis of a non cetrommetric hollow molecular unit(koiand)based on fusion of two p-tert-butylealix[4]arenes byboth silicon and titanium atoms[J].Tetrajedron Lett.,1993,34(47):7561-7564.
102.杨发福,陈远荫.大环杯芳烃冠醚的研究现状与展望[J].合成化学,2003,11(3):203-208.
103.Izatt N.E.,Bruening R.L.,Krakowiak K.E.,etal.Contributions of professor Reed M.Izatt to molecular recogimtion technology:from laboratory to commercial application[J].Ind.Eng.Chem.Res.,2000,39:3405-3411.
104.Casnti A.,Bonetti F.,Sansone F.,et al.Experimental and theoretical evidence of the bidentate binding mode of dichloroacetamido groups at the upper rin of calix[4]arene hydrogen-bonding anion receptors[M].Collection of Czechoslovak Chemical Communications,2004,69(5):1063-1079.
105.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 Chew.Int.Ed.Engl.,2005,44(11):1672-1675.
106.Liu Y.,Wang H.,Zhang H.Y.,et al.Metallo-capped polyrotaxane containing calix[4]arenes and cyclodextrins and its highly selective binding for Ca~(2+)[J].Chem.,Commun(Camb),2004,21(20):2266-2267.
107.Hu J.X.,Leonard J.,Gokel George W.Probing alkali metal-p interactions with the side chain reside of tryptophan[J].Proceedings of the national academy of sciences of the united states of aneicis,2002,124(31):9022-9023.
108.王云艳,蔡亚华,颜朝国.杯芳烃树枝型酰胺衍生物的合成和对金属离子的识别[J].应用化,2006,23(3):278-280.
109.Kim B.,Balasubramanian R.,Walesk P.,et al.Self-Assembly of Resorcinarene-Stabilized Gold Nanopartiele Arrays.Supramol[M].Chem.,2005,17:173-180.
110.吴萍,韩军,戈云,等.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.
111.Buldmann P.,Pretsche E.,Badder E.Ion-selective electrodes and bulk opt odes[J].Chem.Rev,1998,8(4):1593-1595.
112.Oconnor F.,Svehla A.,et al.Calixarenes-based potentiometer ion-selective electrodes for silver[J],Talanta.,1992,39(11):1594-1599.
113.Malinowska E.,Brzozxa Z.Silver selective electrode based on throatier fictionalized calyx[4]arenas as ionospheres[J].Anal Chem.Acta.,1994,298(2):253-256.
114.Carden D.E.,Diamond D.,Miller A.J.An improved Na~+ selective microelectrode for intracellular measurements in plant cells[J].Exp Bot.2001,52(359):1353-1358.
115.Oconnor K.,Svehla G.,Harris S.J.,et al.Calixarenes-based potentiometer ion-selective electrodes for silver[J],Talanta.,1992,39(11):1594-1599.
116.Malinowska E.,Brzrzka Z.,Kasiura Y.,et al.Silver selective electrodes based on thioether functionalizedcalix[4]arenes as ionophores[J].Anal.Chim.Acta.,1994,298:245-248.
117.Buffenoir A.,Bidan Q.,Chalumeau B.,et al.Immobilisation at an electrode surface of calix[4]arches bearing electropolymerisable[J].Electroanal.Chem.,1998,451:261-267.
118.Arrigan D.M.,Svehla Q.,Harris S.J.,et al.Use of calixarenes as modifiers of carbon paste electrodes or voltammetric analysis[J].Electroanalysis,1994,6:97-102.
119.王志欣,陈义.杯芳烃涂层毛细管分离单胺类神经递质[J].化学通报,2001(4):243-2440.
120.Buriks R.S.,Fauke A.R.,Mange F.E.Oxyalkylated Cyclic Phenol-Aldehyde Resins and Uses [J].U.S.Patent.,1977,4(32):514.
121.郑炎松,沈之荃.杯芳烃的催化性质[J].化学通报,1998,4:27-31.
122.Cacciapaglia R.,Casnati A.,Mandolini L.,et al.Remarkable Metal ion Catalysis of Methanolysis of O,O'-oxybis(ethyleneoxyethylerre)-tert-butylealix[4]arene Monoacetate[J].J.Chem.Soc.Commun(S0022-4936).,1992(18):1291-1293.
123.Casnati A.,Cacciapagli A.R.,Luigi M.,et al.The Barium(Ⅱ)Complex of p-tert-butylealix[4]areue-crown-5:a Novel Nucleo-philic Catalyst with Transacylase Activity[J].J.Am.Chem. Soc(S0002-7863).,1992,114(27):10956-10958.
124.Baldini L.,Bracchini C.,Cacciapaglia R.,et al.Catalysis of Acyt Group Transfer by a Double-Displacement Mechanism:TheCleavage of Aryt Esters Catalyzed by Calixcrown-Ba~(2+)Complexes[J].Chem.Eur.J.(S0947-539).,2000,6(8):1318-1321.
1.刘育,尤长城,张衡益.超分子化学[M].天津:南开大学出版社,2001:333-356.
2.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.Soc.,1999,20:953-956.
3.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,2002,12:1040-1043.
4.杨发福,蔡秀琴,季衍卿,等.含酰胺和硫脲单元的杯[4]芳烃衍生物的合成[J].合成化学,2005,13:53-54.
5.王云艳,蔡亚华,颜朝国.杯芳烃树枝型酰胺衍生物的合成和对金属离子的识别[J].应用化学,2006,23(3):278-282.
6.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.
7.Dieleman C.,Steyer S.,Jeunesse C.et al.Diphosphine based on an inherently chiral ealix[4]arene scaffold:synthesis and use in enantioselective catalysis[J].J.Chem.Soc.Dalton Trans.,2001:2508-2517.
8.Bohmer V.Calixarenes macrocycles with(almost)unlimited possibilities[J].Angew.Chem.Int.Ed.Engl.,1995,34:713-745.
9.Oueslati I.,Abidi R.,Thuery P.,et al.Synthesis and complexing properties of methylated calix[4](aza)crown derivatives[J].Tetrahedron,2000,41:8263-8267.
10.Oueslati I.,Abidi R.,Thuery P.,et al.Synthesis and eomplexing properties of methylated calix[4](aza)crown derivatives[J].Tertahedron,2000,41:8263-8267.
11.赵邦屯.一些杯[4]芳烃衍生物的分子识别及其组装[D].南开大学博士论文,2001:24-30.
1 Bohmor V.Calixarenes,macrocycles with(almost)unlimited possibilities[J].Angew.Chem.,Int.Ed.Engl.,1995,34:713-717.
2 Marchand A.P.,Chong H.S.,Takhi M.,et al.Svnthesis and alkali metal pirate extraction studies of Ptert-Butyl-Calix[4]arene crown ethers bridged at the lower rim with pyridy 1 units[J].Tetrahedron,2000,56(20):3121-3129.
3 Zhang W.C.,Zhu Y.,Li E.C.,et al.Synthesis conformation and metal-binding properties of calix[6]agene derivatives[J].Tetrahedron,2000,56(21):3365-3370.
4 Jung Y.E.,Song B.M.,Chang S.K.Molecular recognition of alkyl-and arylalkyl-amines in dichloromethane and chloroform by Calix[4]-Crown ethers[J].J.Chem.Soc.Perkins Trans.,1995(2):2031-2037.
5 Van Loon J.D.,Janssen R.G.,Verboom W.et al.Hydrogen bonded calix-[41arene aggregates[J].Tetrahedron Lett.,1992,33(35):5125-5128.
6 Mogek O.,Boehmer V.,Vogt W.Hydrogen bonded homo-and heterodimers of tetraurea derivatives of calix[4]arenes[J].Tetrahedron,1996,52(25):8489-8496.
7 Gutsehe C.D.,Dhawan B.,No K.H.,et al.Calixarenes[4]The synthesis characterization and properties of the ealixarenes from ptert-butylphenol[J].J.Am.Chem.Soc.,1981,103(13):3782-3792.
8 舒和庆,张蓉仙,沈小平.新型双-1,2-酰胺桥联杯[4]芳烃对碱金属苦味酸盐的加合性质[J].江苏大学学报,2004,25:172-173.
9 陈淑华,李东红,袁立华等.杯芳烃受体的分子识别作用研究进展[J].有机化学,1999,19(4):339-347.
10 Oueslati I.,Abidi R.,Thuery P.,et al.Synthesis of calix[4]arene(amido)monocrowns and their photoresponsive derivatives[J].Tetrahedron.Lett.,2000,41:8263-8265.
1.陈素萍.第三代主体超分子化合物-杯芳烃的研究[J].南通职业大学学报,2005,19(4):104-108.
2.Yang F.F.,zhao x.,Huang H.Y.et al.Synthesis and Complexation Properties of Novel Biscalixarene Composed of Calix[4]arene and Thiacalix[4]arene Subunits[J].Chin.Chem.Letters.,2006,17(8):1029-1032.
3.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.Soc.,1999,20(8):953-956.
4.Wan B.W.,Jin C.M.,Guo X.,et al.Synthesisof schiff base calix 4 arene crowns[J].Chin.Chem.Lett.,2002,13(6):699-700.
5.杨发福,黄翠玉,赵夏,等.硫杂杯-1,3-2,4-氮杂双冠醚的合成与氨基酸配合性能.高等学校化化学报[J],2007,28(5):885-888.
6.Song K.C.,Choi M.G.,Ryu d.H.,et al.Rationetric chemosensing of Mg~(2+)ions by a calix[4]arene diamide derivative[J].Tetrahedron Lett.,2007,48:5397-5400.
7.Gulderen U.A.,Shahabuddin M.,Dilek E.G,et al.The synthesis and metal cation extraction studies of novel polymer-bound calix(aza)crowns[J].Functional Polymers,2008,68:125-132.
8.吕鉴泉,何锡文,陈朗星,等.新型主体分子噻唑偶氮基杯[n]芳烃衍生物的合成及其对重金属离子的识别[J].高等学校化学学报,2002,23(2):191-194.
9.赵邦屯.一些杯[4]芳烃衍生物的分子识别及其组装[D].南开大学博士论文,2001:24-30.
10.刘顺英,王法军,隗兰华,肖旺等.多酰胺杯[4]芳烃中性阴离子受体的合成与识别性能[J].中国科学,2003,33(6):504-510.
11.Connors K.A.,Binding Constants[M],John Wiley and Sons,1987:126-130.
12.Xiao Y.J.,Wu X.J.,He Y.B.,et al.Synthesis of a New Type Tetraamides Bridged Calix[4]arene[J].Aeta Chimica sinica,2003,61(6):1986-1990.
2.Lehn J.M.Supramolecular chenistry-scope perspectives molecules,supermolecules evices[J].Angew.Chem.Int.Ed.Engl.,1988,27:89-112.
3.Bohmer V.Calixarenes macrocycles with(almost)unlimited possibilities[J].Angew.Chem.Int.Ed.Engl.,1995,34:713-745.
4.Pochini R.,Ungaro R.,"Calixarenes and related hosts"[J].comprehensive supramolecular chemistry,Pergamon Press Oxford,1996,(2):103-105.
5.赵邦屯,张衡益,刘育.基于杯芳烃主体的分子自组装研究进展[J].有机化学,2005,25(8):913-925.
6.Casnati A.,Sansone F.Ungaro R.,Peptido and glycocalixarenes:playing with hydrogen bonds around hydrophobic cavities[J].Acc.Chem.Res.,2003,36:246-254.
7.王春,何锡文.超分子在质量敏感压电化学传感器中的应用[J].分析测试学报,2001,20(1):84-87.
8.张书胜,何新亚.杯芳烃及其衍生物在色谱和毛细管电泳中的应用[J].化学通报,2001,64(4):226-231.
9.Ikeda A.,Shinkai S.Novel Cavity design using calix[n]arene skeletons:toward molecular recognition and metal binding[J].Chem.Rev.,1997,97:1710-1734.
10.郑炎松.杯芳烃的配位性质[J].化学进展,1999,11(3):275-285.
11.Ngah W.,Endud C.S.,Mayanar R.Removal of copper(Ⅱ)ions from aqueous solution onto chitosan and cross-linked chitosan beads[J].Reactive and Functional Polymers,2002,50(2):181-190.
12.王建玲,林琳.杯芳烃固定液分子识别的热力学性质[J].分析测试学报,1998,17(5): 40-43.
13.Baeyer A.Ueber der Verbindungen der Aldehyde Unit den Phenolen and Aromatischen Kohlenwasser Stoffen[J].Chem.Ber,1872,25:1094-1010.
14.Zinke A.,Ziegler E.,Zur Kenntnis des Hartungs-prozesses yon phenol Formaldehyde Harzen[J].Chem.Ber.,1944,77:264-269.
15.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.,1978,43:4905-4910.
16.Molenveld P.,Engbersen J.F.,Reinhoudt D.N.,et al.Dinuclear bisimi-dazolyl-Cu calix[41arenes as metalloenzyme models,synthesis and bifunctional catalysis in phosphate diester transe-sterification[J].J.Org.Chem.,1999,64:6337-6342.
17.Rondelez Y.,Sdndque Q.,Rager,M.et al.Biomimetic copper(1)CO complexes:a structural and dynamic study of a calix[6]arene-based supramolecular system[J].Eur.J.Chem.,2000,6:4218-4223.
18.郭兵,冯亚青等.新型主体分子-杯芳烃研究进展[J],合成化学,2000,8(5):395-398.
19.刘育,尤长城,张衡黼.超分子化学[M].天津:南开大学出版社,2001:333-356.
20.Gutsche C.D.,Dhawan B.,Levine L.A.Calixarens,royal society of chemistry[J].J.Am.Chem.Soc.,1982,104:2652-2655.
21.Knop A.,Bohmer V.,Pilato L.A.Phenol-Formaldehyde polymers[J].Comprehensive Polymer Science,1989(5):611-647.
22.Nakamoto Y.,Ishida S.I.Calix[7]arene from 4-tert-butylphenol and formaldehyde[J].Makromol Chem.Rapid Commun,1982,3:705-710.
23.Dumazet J.B.,Regrnouf-de-Vains R.Lamartime.Sythesis and characterization of p-tert-butyl-cllix[9,10,11 and 12]arenes[J],Synth.Commun,1991,27:2547-2551.
24.Hayes B.T.,Hunter R.F.Phemol-formaldehyde and alliedresins Ⅵ:Rationl synthesis of a cyc -lic tetramuclear p-cresol novolak[J].Appl.Chem.,1958,8:743-748.
25.Facile K.No.Synthesis of p-phenyl homooxa-calix[4]arenes[J].Bull Korean chem.Soc.,1999,20(1):33-35.
26.Bohmer V.,Merkel L.,Kunz U.Calix[4]arenes with four differently substituted phenolic units[J].J.Org.Chem.,1987,35:896-899.
27.Bohmer V.,Jung K.,Schoen M.,etal.Direct symthesis of calix[4]arenes with two different phenolic units in alitermating order[J].J.Org.Chem.,1992,57:790-794.
28.Pagoria P.F.,Gutsche C.D.Functionalized calixarenes:the direct substitution route[J].J.Org.Chem.,1984,88(7):106-120.
29.Fu D.K.,Xu B.,Swager T.M.3-methylcalix[4]arene:a new versalile precursor to inherently chiral calix[4]arene[J],J.Org.Chem.,1996,61:802-808.
30.Zhong Z.L.,Li J.S.,Lu X.R.,et al.The imporovement of the cyclization step in the stepwicse synthesis of calix[4]arenes[J].Chem.Chinese Univ.,1998,19:83-86.
31.Sone T.,Ohba Y.,Oriya K.,et al.Synthesis and properties of sulfur-bridged analogs of p-tert-But-ylclaix[4]arene[J].Tetrahedron,1997,53:10689-10692.
32.Kumagai H.,aseawa M.,iyamari S.,ctal.Facile synethesis 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.
33.Hoorn W.P.,rank C.J.M.,einhoudt D.N.Conformatonal characteristcs of ethers and esters of p-tert-butylcalix[5]arene[J].J.Org.Chem.,1996,61:7180-7184.
34.Levine L.A.,Gutsche C.D.Calixarene,royal society of chemistry[J].J.Am.Chem.Soc.,1982,104:2652-2655.
35.陆国元,陈中俊.杯[4]芳烃衍生物的合成和构象研究[J].高等学校化学学报,1996,17(8):1244-1246.
36.李建森,陈远荫.桥联杯[6]芳烃研究进展[J].有机化学,2000,20(6):841-849.
37.苏晓渝,谢如刚.超分子自组装中的非共价键协同作用[J].化学研究与应用,2007,19(12):1304-1310.
38.钟志梅,姚俊学.杯芳烃及其衍生物的研究进展[J].内蒙古石油化工,2005,31(2):9-11.
39.Bell S.E.J.,Browne V.,McKee M.A.,et al.Structure of p-Phenylcalix[5]arene Dichloroform Solvate[J].J.Chem.Soc.,2005,26(2):337-341.
40.Grote G.M.,Verboom W.,Veggel F.C.,et al.Conformational extremes in the suoramolecular assemblies of para-sjlronato-calix[8]arene[J].J.Chem.Soc.,2006,30:987-990.
41.Rudkevich D.M,Verboom W.Supramolecular Structures fron Lysine Peptides and Carbon Dioxide[J].J.Org.Chem.,2006,71:8696-8705.
42.陈朗星,郭洪声,何锡文.杯芳烃的功能化修饰及其在分子识别中的应用[J].化学进展,2001,13(3):210-215.
43.Mairana D.,Zouhair A.,Natalia K.,et al.Thiacrowncalix[4]arene derivatives:synthesis and complexing properties[J].Super.Chem.,2005,17(3):221-226.
44.Seangpraserkij R.,Asfari Z.,Amaud F.,et al.Schiff base p-tert-butylcalix[4]arenes,synthesis and metal ion complexation[J].J.Org.Chem.,199459:1741-1745.
45.Rudkevich D.M.,Veboom W.,Reinhoudt D.N.Calix[4]arene salenes:A bifunctional receptor for NaH_2PO_4[J].J.Org.Chem.,1994,59:3683-3688.
46.Bohmer V.,Mogck O.,Ports M.,et al.NMR studies of the renersible dimerization and guest exchange processes of tetra urea calix[4]arenes using a derivative with lower syrmetry[J].J.Am.Chem.Soc.,1997,16:1581-1585.
47.Gusche C.D.,Nam K.C.Synthesis,porperties and metal complexation of aminocalixarenes[J].J.Am.Chem.Soc.,1988,110:6153-6157.
48.Casellato U.,Tamburini S.,Tomasin P.,et al.Heero-dinuclear sodium-lanthanide(Ⅲcomplexes with an asymmetric compartmental macrocycle[J].Chem.,Common.,2000,2:145-146.
49.Li X.,Gong S.L.,Zhang C.L.,et al.(1+1)or(2+2)Coupling for bis(tosyloxyethoxy)benanenes with calix[4]arene and thiacalix[4]arene[J].Tetrahedron letters,2006,47:7695-7698.
50.张德华,吕鉴泉.芘冠醚双功能化杯[4]芳烃的合成与表征[J].化学试剂,2006,28(10):627-628,631.
51.王巍,龚淑玲,孟令芝,等.单炔基桥联双杯[4]芳烃的合成与对溶剂分子的包合性能[J].高等学校化学学报,2005,26(8):1467-1470.
52.Castellano R.K.,Nuckolls C.,Rebek J.Transfer of chiral information through molecular assembly[J].J.Am.Chem.Soc.,1999,121:11156-11163.
53.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.
54.Vazquez M.L.,Franco C.M.,Cepeda A.,et al.Liquid chromatographic study of the interaction between aflatoxins and β-cyclodextrin[J].Anal.Chem.Acta.,1992,269:239-247.
55.郑琴,龚淑玲,张春雷,等.双杯芳烃研究进展[J].化学进展,2007,19(5):722-734.
56.Beer P.D.,Keefe A.D.Slawin A.M.Z.,et al.Highly Ordered Smectic Phases from Polar Calix[4]arene Derivatives[J].J.Chem.Soc.Dalton Tram.,1990,(12):3675-3682.
57.Shinkai S.Araki K.,Matsuda T.,et al.NMR and crystallographic studies of p-sulfonatocalix[4]arene-guest complex[J].J.Am.Chem.Soc.,1990,112(25):9053-9058.
58.Santoyo-Gonzalez E,Tortes-Pinedo A.,Barria C.S.Mono-and Dinuclear Oxovanadium (V)calixarene Complexes and Their Activity as Oxidation Catalysts[J].J.Org.Chem.,2000(21):3587-3593.
59.Beer P.D.,Gale P.D.,Hesek D.Synthesis and characterization of chiral catenanes based on rigid calix[4]arene[J].Tetrahedron Lett.,I995,36(5):767-770.
60.杨发福,郑林禄,季衍卿等.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(2):268-270.
61.吉傲,郑炎松,刘劲强,等.含氮杯[4]芳烃的合成[J].化学与生物工程,2007,24(4):44-46.
62.安琳,颜朝国.杯芳烃偶氮类衍生物对金属离子的萃取作用[J].化学研究,2007,18(1):84-85.
63.戈云,吴萍,韩军,等.四-(p羟基苯基)杯[4]间苯二酚芳烃的烃基化和酰胺化反应[J].有机化学,2006,26(5):681-684.
64.肖元晶,吴晓军,曾振亚,等.一类新型四酰胺杯[4]氮杂冠醚的合成及阴离子识别研究[J]. 化学学报,2003,61(12):1986-1990.
65.Ivan I.,Omran A.,Svetlana E.,et al.The synthesis of tetracarbonyl derivatives of thiacalix[4]aren -e in different conformations and their complexation properties towards alkali metal ions[J].Tetrahedron,2003,59:1469-1476.
66.Iki N.,Morohashi N.,Narumi F.,et al.Novel molecular receptors based on a thiacalix[4]arene platform.Preparations of the di-and tetracarboxylic acid derivatives and their binding properties towards transition metal ions[J].Tetrahedron Letters,1999,40:7337-7341.
67.Tastny'V.,Stibor I.,Dvori H.,et al.Synthesis of(thia)calix[4]arene oligomers:towards calixarene-based dendrimers[J].Tetrahedron,2004,60:3383-3391.
68.夏琳,邱桂学.化学科学的研究新领域-超分子化学[J].化学推进剂与高分子材料,2007,5(1):33-37.
69.张穗娟,李琼芳,李如芳.关于超分子化学[J].广东化工,2004,31(6):36-37.
70.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.
71.Chawia H.M.,Srinivas K.Synthesis of new chromogenic calix[8]arenes as potential reagents for detection of amines[J].J.Chem.Soc.,Chem.Comrnun.,1994.1(220):2593-2594.
72.Zhang L,Agodinea L.,LuT.,et al.Preparative Enantiomer Separation of the Anesthetic Enflurane by Gas Inclusion Chromatography[J].Angew.Chem.Int.Ed.Engl.1990,29:939-941.
73.Nakamato Y.,Ishida S.Calix[7]Arene from 4-tert-butylphenol and fromaldehyde[J].Makromol Chem.Rapid Commun.,1982,3:705-707.
74.Barteri M.,Pispisa B.Effeet of pH on thestreospeclfic peroxidatic activity of Chiral association complexes between iron(111)chelate ions and polypeptides[J].MakromoI Chem.Rapid Commun.,1982:715-721.
75.Bott S.G.,Coleman A.W.,Atwood J.L.Intercalation of cationic,anionic and Molecular species by organic hosts.Prevaration and crystal structure of[NH_4]_6[calix[4]arenesulfonate][MeOSO_3].cnt-dot(H_2O)_2[J].J.Am.Chem.Soc.1988,110:610-611.
76.MckerVey M.A.,Seward E.M.,Ferguson G.,et al.Synthesis and x-ray crystal slructure of a calixI4]arene tetracarbonate-acetonitrile(1:1)chathrate[J].J.Org.Chem.1986,51:3581-3584.
77.Rizzoli C.,Andreetti G.D.,Ungaro R.,et al.On the separalion of motions in theory of polyatomic molecularspectra[M].J.Mol.Struct.,1982,87:133-139.
78.Aoyama Y.,Tanaka Y.,Toi H.,et al.Transport from Multiple Alk-ali Cation Mixture Using a Liquid Membrane System Containing a Series of Calixarene Carriers[J].J.Am.Chem.Soc.,1988,1110:634-636.
79.陈再鸿,林俊,郑南峰,等.球烯与对叔丁基杯[8]烃苯醚形成超分子包合物的研究[J].厦门大学学报(自然科学版),1999,38(4):547-551.
80.Atwood J.L.,Kontsantonis G.A.,Raston C.L.Purification of C60 andC70 by selective complexation with calixarenes[J].Nature.,1994,368:229-231.
81.Gutsche C.D,Levine.L.Synthesis of a Functionalizable Calix[4]arene in a Conformationally Rigid Cone Comformation[J].J.Am.Chem.Soc.,1982,104:2652-2655.
82.史春越,曹家庆,范平.杯芳烃对有机小分子识别作用的研究进展[J].辽宁大学学报(自然科学版),2003,30(1):82-86.
83.Zielenkiewicz W.,Mareinowiez A.,Poznanski J.,et al.Compexation of isoleucine by phosphorylated calyx[4]arene in methanol,followed by calorimetry,NMR and UV-VIS spectroscopies and molecular modeling methods[J].Journal of Molecular Liquids,2005,121:8-14.
84.Liu Y.,Ma Y.H.,Chen Y.,et al.Molecular recognition thermodynamics of pyridine derivatives by sulfonatocalixarenes at different pH values[J].J.Org.Chem.,2006,71:6468-6473.
85.韩宝航,刘育,陈荣悌.水溶性杯芳烃对染料客体分子的包结配位作用[J].化学学报,2001,59(4):550-555.
86.Mate S.K.,Szabo K.,Lemli B.,et al.Host-guest interaction between water-soluble calix[6]arene hexasulfonate and p-nitrophenol[J].Thermochimiea Acta,2005,425:121-126.
87.Iwamolto K.,Araki K.,Shimkai S.Conformations and Struerures of Tetra-o-alkylptert-butylca lis[4]arene[J].J.Org.Chem.1991,56:4956-4962.
88.Shinkai S.,Araki K.,Koreishi H.On the Acidity of the Hydroxyl G roup in Calixarenes and the Dissociation-dependent Conformational Change[J].Chem.Lett.,1986,56:1351-1353.
89.Shinkai S.On the Origin of High Ionophricity of 1,3-Alternate Calix[4]arenes[J].J.Am.Chem.Soc.,116:3102-3110.
90.Chawia H.M.,Srimivas K.Syntyesis and Structure of a Capping Calix[6]arenewith 1,2,4,5-etra-kis(bromomethyl)benzene[J].Tetrahedron.1995,51:2709-2711.
91.Doneld B.,Gary D.C.,Domenico C.Asylnmetrically-substituted Calix[4]arene[J].J.Chem.Soc.,chem.commum.,1995:675-678.
92.Loeber C.,Matt D.Alremation Alkylation of p-tert-Calixarene in the Precenee of weak base[J].J.Org.Chem.,1995,60:4126-4128.
93.Chawla H.M.,Srinivas K.Synthesis of new chromogenic calix[8]arenes[J].Tetrahedron Letters.1994,35:2925-2928.
94.陈淑华,李东红.杯芳烃类受体的分子识别作用研究进展[J].有机化学,1999,19(4):339-347.
95.Pudkebich D.,Verhoeven M.,Reinhoudt D.5,9-Methanobenzoannulenam In-es Improved synthesis of 11-amino-5,9-methanobenzo[8]annulenes[J].J.Chem.Soc.Perkin Transl.1995,1:133-140.
96.袁立华,黄枢.靛酚型生色杯[4]芳烃及其与金属离子络合的紫外-可见光谱研究[J].合成化学.1995,3(3):194-197.
97.余天祥,杨先金.杯[4]双硫脲化合物的合成及其对H_2PO_4~-络合作用[J].武汉大学学报:自然科学版,1999,45(6):811-813.
98.Bulgler J.,Hoek A.,et al.Interconnective host-fuest complexation of cyclodextrin-calix[4]arene couples[J].J.Am.Chem.Soc.,1999,121:28-33.
99.Halouani H.,Bonnamour I.D.,Perrin M.,et al.First synthesis and struture of ketoimine calix[4]arene:complexation and extraction studies[J].J.Org.Chem.,2004,69:6521-6527.
100.Metibier R.,Leray I.,Valeur B.Lead and mercury sensing by calixarene based fluoroionophores bearing two or four dansyl fluorophores[J].J.Chem.Eur.,2004,10:4480-4490.
101.Deligue X.Multicavitands Ⅱ:Synthesis of a non cetrommetric hollow molecular unit(koiand)based on fusion of two p-tert-butylealix[4]arenes byboth silicon and titanium atoms[J].Tetrajedron Lett.,1993,34(47):7561-7564.
102.杨发福,陈远荫.大环杯芳烃冠醚的研究现状与展望[J].合成化学,2003,11(3):203-208.
103.Izatt N.E.,Bruening R.L.,Krakowiak K.E.,etal.Contributions of professor Reed M.Izatt to molecular recogimtion technology:from laboratory to commercial application[J].Ind.Eng.Chem.Res.,2000,39:3405-3411.
104.Casnti A.,Bonetti F.,Sansone F.,et al.Experimental and theoretical evidence of the bidentate binding mode of dichloroacetamido groups at the upper rin of calix[4]arene hydrogen-bonding anion receptors[M].Collection of Czechoslovak Chemical Communications,2004,69(5):1063-1079.
105.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 Chew.Int.Ed.Engl.,2005,44(11):1672-1675.
106.Liu Y.,Wang H.,Zhang H.Y.,et al.Metallo-capped polyrotaxane containing calix[4]arenes and cyclodextrins and its highly selective binding for Ca~(2+)[J].Chem.,Commun(Camb),2004,21(20):2266-2267.
107.Hu J.X.,Leonard J.,Gokel George W.Probing alkali metal-p interactions with the side chain reside of tryptophan[J].Proceedings of the national academy of sciences of the united states of aneicis,2002,124(31):9022-9023.
108.王云艳,蔡亚华,颜朝国.杯芳烃树枝型酰胺衍生物的合成和对金属离子的识别[J].应用化,2006,23(3):278-280.
109.Kim B.,Balasubramanian R.,Walesk P.,et al.Self-Assembly of Resorcinarene-Stabilized Gold Nanopartiele Arrays.Supramol[M].Chem.,2005,17:173-180.
110.吴萍,韩军,戈云,等.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.
111.Buldmann P.,Pretsche E.,Badder E.Ion-selective electrodes and bulk opt odes[J].Chem.Rev,1998,8(4):1593-1595.
112.Oconnor F.,Svehla A.,et al.Calixarenes-based potentiometer ion-selective electrodes for silver[J],Talanta.,1992,39(11):1594-1599.
113.Malinowska E.,Brzozxa Z.Silver selective electrode based on throatier fictionalized calyx[4]arenas as ionospheres[J].Anal Chem.Acta.,1994,298(2):253-256.
114.Carden D.E.,Diamond D.,Miller A.J.An improved Na~+ selective microelectrode for intracellular measurements in plant cells[J].Exp Bot.2001,52(359):1353-1358.
115.Oconnor K.,Svehla G.,Harris S.J.,et al.Calixarenes-based potentiometer ion-selective electrodes for silver[J],Talanta.,1992,39(11):1594-1599.
116.Malinowska E.,Brzrzka Z.,Kasiura Y.,et al.Silver selective electrodes based on thioether functionalizedcalix[4]arenes as ionophores[J].Anal.Chim.Acta.,1994,298:245-248.
117.Buffenoir A.,Bidan Q.,Chalumeau B.,et al.Immobilisation at an electrode surface of calix[4]arches bearing electropolymerisable[J].Electroanal.Chem.,1998,451:261-267.
118.Arrigan D.M.,Svehla Q.,Harris S.J.,et al.Use of calixarenes as modifiers of carbon paste electrodes or voltammetric analysis[J].Electroanalysis,1994,6:97-102.
119.王志欣,陈义.杯芳烃涂层毛细管分离单胺类神经递质[J].化学通报,2001(4):243-2440.
120.Buriks R.S.,Fauke A.R.,Mange F.E.Oxyalkylated Cyclic Phenol-Aldehyde Resins and Uses [J].U.S.Patent.,1977,4(32):514.
121.郑炎松,沈之荃.杯芳烃的催化性质[J].化学通报,1998,4:27-31.
122.Cacciapaglia R.,Casnati A.,Mandolini L.,et al.Remarkable Metal ion Catalysis of Methanolysis of O,O'-oxybis(ethyleneoxyethylerre)-tert-butylealix[4]arene Monoacetate[J].J.Chem.Soc.Commun(S0022-4936).,1992(18):1291-1293.
123.Casnati A.,Cacciapagli A.R.,Luigi M.,et al.The Barium(Ⅱ)Complex of p-tert-butylealix[4]areue-crown-5:a Novel Nucleo-philic Catalyst with Transacylase Activity[J].J.Am.Chem. Soc(S0002-7863).,1992,114(27):10956-10958.
124.Baldini L.,Bracchini C.,Cacciapaglia R.,et al.Catalysis of Acyt Group Transfer by a Double-Displacement Mechanism:TheCleavage of Aryt Esters Catalyzed by Calixcrown-Ba~(2+)Complexes[J].Chem.Eur.J.(S0947-539).,2000,6(8):1318-1321.
1.刘育,尤长城,张衡益.超分子化学[M].天津:南开大学出版社,2001:333-356.
2.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.Soc.,1999,20:953-956.
3.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,2002,12:1040-1043.
4.杨发福,蔡秀琴,季衍卿,等.含酰胺和硫脲单元的杯[4]芳烃衍生物的合成[J].合成化学,2005,13:53-54.
5.王云艳,蔡亚华,颜朝国.杯芳烃树枝型酰胺衍生物的合成和对金属离子的识别[J].应用化学,2006,23(3):278-282.
6.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.
7.Dieleman C.,Steyer S.,Jeunesse C.et al.Diphosphine based on an inherently chiral ealix[4]arene scaffold:synthesis and use in enantioselective catalysis[J].J.Chem.Soc.Dalton Trans.,2001:2508-2517.
8.Bohmer V.Calixarenes macrocycles with(almost)unlimited possibilities[J].Angew.Chem.Int.Ed.Engl.,1995,34:713-745.
9.Oueslati I.,Abidi R.,Thuery P.,et al.Synthesis and complexing properties of methylated calix[4](aza)crown derivatives[J].Tetrahedron,2000,41:8263-8267.
10.Oueslati I.,Abidi R.,Thuery P.,et al.Synthesis and eomplexing properties of methylated calix[4](aza)crown derivatives[J].Tertahedron,2000,41:8263-8267.
11.赵邦屯.一些杯[4]芳烃衍生物的分子识别及其组装[D].南开大学博士论文,2001:24-30.
1 Bohmor V.Calixarenes,macrocycles with(almost)unlimited possibilities[J].Angew.Chem.,Int.Ed.Engl.,1995,34:713-717.
2 Marchand A.P.,Chong H.S.,Takhi M.,et al.Svnthesis and alkali metal pirate extraction studies of Ptert-Butyl-Calix[4]arene crown ethers bridged at the lower rim with pyridy 1 units[J].Tetrahedron,2000,56(20):3121-3129.
3 Zhang W.C.,Zhu Y.,Li E.C.,et al.Synthesis conformation and metal-binding properties of calix[6]agene derivatives[J].Tetrahedron,2000,56(21):3365-3370.
4 Jung Y.E.,Song B.M.,Chang S.K.Molecular recognition of alkyl-and arylalkyl-amines in dichloromethane and chloroform by Calix[4]-Crown ethers[J].J.Chem.Soc.Perkins Trans.,1995(2):2031-2037.
5 Van Loon J.D.,Janssen R.G.,Verboom W.et al.Hydrogen bonded calix-[41arene aggregates[J].Tetrahedron Lett.,1992,33(35):5125-5128.
6 Mogek O.,Boehmer V.,Vogt W.Hydrogen bonded homo-and heterodimers of tetraurea derivatives of calix[4]arenes[J].Tetrahedron,1996,52(25):8489-8496.
7 Gutsehe C.D.,Dhawan B.,No K.H.,et al.Calixarenes[4]The synthesis characterization and properties of the ealixarenes from ptert-butylphenol[J].J.Am.Chem.Soc.,1981,103(13):3782-3792.
8 舒和庆,张蓉仙,沈小平.新型双-1,2-酰胺桥联杯[4]芳烃对碱金属苦味酸盐的加合性质[J].江苏大学学报,2004,25:172-173.
9 陈淑华,李东红,袁立华等.杯芳烃受体的分子识别作用研究进展[J].有机化学,1999,19(4):339-347.
10 Oueslati I.,Abidi R.,Thuery P.,et al.Synthesis of calix[4]arene(amido)monocrowns and their photoresponsive derivatives[J].Tetrahedron.Lett.,2000,41:8263-8265.
1.陈素萍.第三代主体超分子化合物-杯芳烃的研究[J].南通职业大学学报,2005,19(4):104-108.
2.Yang F.F.,zhao x.,Huang H.Y.et al.Synthesis and Complexation Properties of Novel Biscalixarene Composed of Calix[4]arene and Thiacalix[4]arene Subunits[J].Chin.Chem.Letters.,2006,17(8):1029-1032.
3.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.Soc.,1999,20(8):953-956.
4.Wan B.W.,Jin C.M.,Guo X.,et al.Synthesisof schiff base calix 4 arene crowns[J].Chin.Chem.Lett.,2002,13(6):699-700.
5.杨发福,黄翠玉,赵夏,等.硫杂杯-1,3-2,4-氮杂双冠醚的合成与氨基酸配合性能.高等学校化化学报[J],2007,28(5):885-888.
6.Song K.C.,Choi M.G.,Ryu d.H.,et al.Rationetric chemosensing of Mg~(2+)ions by a calix[4]arene diamide derivative[J].Tetrahedron Lett.,2007,48:5397-5400.
7.Gulderen U.A.,Shahabuddin M.,Dilek E.G,et al.The synthesis and metal cation extraction studies of novel polymer-bound calix(aza)crowns[J].Functional Polymers,2008,68:125-132.
8.吕鉴泉,何锡文,陈朗星,等.新型主体分子噻唑偶氮基杯[n]芳烃衍生物的合成及其对重金属离子的识别[J].高等学校化学学报,2002,23(2):191-194.
9.赵邦屯.一些杯[4]芳烃衍生物的分子识别及其组装[D].南开大学博士论文,2001:24-30.
10.刘顺英,王法军,隗兰华,肖旺等.多酰胺杯[4]芳烃中性阴离子受体的合成与识别性能[J].中国科学,2003,33(6):504-510.
11.Connors K.A.,Binding Constants[M],John Wiley and Sons,1987:126-130.
12.Xiao Y.J.,Wu X.J.,He Y.B.,et al.Synthesis of a New Type Tetraamides Bridged Calix[4]arene[J].Aeta Chimica sinica,2003,61(6):1986-1990.