基于杯［4］芳烃的光、电活性受体的合成、表征及识别性质研究
|
摘要
鉴于荧光传感和电化学识别受体研究对超分子化学、生命科学以及材料化学发展所具有的重大理论意义,在离子传输、荧光传感器、电化学分子器件和分子开关等高科技领域所具有的重要应用价值,本论文开展了基于杯[4]芳烃的光、电活性受体分子的设计、合成及识别性质研究,取得了创新性的研究成果。主要内容如下:
1、简要总结了基于杯芳烃的光、电活性受体的设计、合成及在超分子荧光传感和电化学识别等方面的研究进展。
2、本论文共设计、合成了2个系列,11种未见文献报道的杯[4]芳烃衍生物,其结构经IR、~1H NMR、~(13)C NMR、MS和元素分析所表征。
3、设计、合成了4种基于1,2,3-triazole杂环桥联的新型二茂铁杯[4]芳烃开链冠醚受体R1-R4。研究发现,受体R1-R4具有优异的电化学性质,可选择性电化学识别H_2PO_4~-、Eu~(3+)、Co~(2+)等阴、阳离子。
4、首次设计、合成了2种基于喹啉为荧光探针基团、1,2,3-triazole杂环为桥联基团的新型杯[4]芳烃开链冠醚受体R5和R6。紫外和荧光滴定研究表明,R5和R6能选择性识别Eu~(3+)、Zn~(2+)等过渡金属离子。
本论文所设计、合成的光、电活性杯[4]芳烃受体不仅丰富了杯芳烃化学的研究内容,而且为构建新型荧光传感器和电化学分子器件提供了一条新的途径,具有重要的理论意义和应用前景。
The investigation on both photochemical sensing and electrochemical recognition is an area of increasing interest. It is great important to both supramolecular chemistry and materials science. The photo- and redox-active receptors are widespread applied in many fields such as ion transport, molecular switches, chemical molecular devices and chemical sensors. Therefore, a study on design, synthesis and recognition properties of calixarene based photo- and redox-active receptors containing ferrocene or quinoline units was carried out. The main results are as follows:
1.The recent development of calixarene based photo- and redox-active receptors, including molecular design, synthesis, and their applications in supramolecular recognition and sensing properties, was briefly reviewed.
2.A total of 11 new calix[4]arene derivatives were synthesized. Their structures were fully characterized by elemental analysis, IR, ~1H NMR, ~(13)C NMR and MS.
3.Four novel calix[4]arene based 1, 2, 3-triazole-bridgrd ferrocene receptors were synthesized in excellent yields via copper(I)-catalyzed azide-alkyne cycloaddition. Their recognition properties towards both cations and anions were investigated by CV and UV methods. It was found that these receptors exhibit a high selectivity for electrochemical sensing of H_2PO_4~-, Eu~(3+)and Co~(2+) ions.
4.The first examples of calix[4]arene based 1,2, 3-triazole-linked quinoline receptors were prepared in good yields by click reaction. Their recognition behaviors towards anion and cation species were studied by UV and fluorescence titration techniques. These receptors show a good selectivity for fluorescent sensing of Zn~(2+) and Eu~(3+) ions.
1、简要总结了基于杯芳烃的光、电活性受体的设计、合成及在超分子荧光传感和电化学识别等方面的研究进展。
2、本论文共设计、合成了2个系列,11种未见文献报道的杯[4]芳烃衍生物,其结构经IR、~1H NMR、~(13)C NMR、MS和元素分析所表征。
3、设计、合成了4种基于1,2,3-triazole杂环桥联的新型二茂铁杯[4]芳烃开链冠醚受体R1-R4。研究发现,受体R1-R4具有优异的电化学性质,可选择性电化学识别H_2PO_4~-、Eu~(3+)、Co~(2+)等阴、阳离子。
4、首次设计、合成了2种基于喹啉为荧光探针基团、1,2,3-triazole杂环为桥联基团的新型杯[4]芳烃开链冠醚受体R5和R6。紫外和荧光滴定研究表明,R5和R6能选择性识别Eu~(3+)、Zn~(2+)等过渡金属离子。
本论文所设计、合成的光、电活性杯[4]芳烃受体不仅丰富了杯芳烃化学的研究内容,而且为构建新型荧光传感器和电化学分子器件提供了一条新的途径,具有重要的理论意义和应用前景。
The investigation on both photochemical sensing and electrochemical recognition is an area of increasing interest. It is great important to both supramolecular chemistry and materials science. The photo- and redox-active receptors are widespread applied in many fields such as ion transport, molecular switches, chemical molecular devices and chemical sensors. Therefore, a study on design, synthesis and recognition properties of calixarene based photo- and redox-active receptors containing ferrocene or quinoline units was carried out. The main results are as follows:
1.The recent development of calixarene based photo- and redox-active receptors, including molecular design, synthesis, and their applications in supramolecular recognition and sensing properties, was briefly reviewed.
2.A total of 11 new calix[4]arene derivatives were synthesized. Their structures were fully characterized by elemental analysis, IR, ~1H NMR, ~(13)C NMR and MS.
3.Four novel calix[4]arene based 1, 2, 3-triazole-bridgrd ferrocene receptors were synthesized in excellent yields via copper(I)-catalyzed azide-alkyne cycloaddition. Their recognition properties towards both cations and anions were investigated by CV and UV methods. It was found that these receptors exhibit a high selectivity for electrochemical sensing of H_2PO_4~-, Eu~(3+)and Co~(2+) ions.
4.The first examples of calix[4]arene based 1,2, 3-triazole-linked quinoline receptors were prepared in good yields by click reaction. Their recognition behaviors towards anion and cation species were studied by UV and fluorescence titration techniques. These receptors show a good selectivity for fluorescent sensing of Zn~(2+) and Eu~(3+) ions.
引文
1.(a)Lehn,J.- M.Angew.Chem.,Int.Ed.Engl.1988,27,89.(b)Lehn,J.- M.Angew.Chem.,Int.Ed.Engl.1990,29,1304.(c)Liu,Y.;You,C.H.;Zhang,H.Y.Supramolecular Chemitry Molecular Recognition and Assembly of Synthetic Receptors.Nan Kai University Press 2001.
2.Gutsche,C.D.In Calixarenes,in Monographs in Supramolecular Chemistry,Ed.Stoddart,J.F.Royal Society of Chemistry,London,1989.
3.Bohemer,V.Angew.Chem.,Int.Ed.Engl.1995,34,715.
4.Takeshita,M.;Shinkai,S.Chem.Soc.Jpn.1995,68,1088.
5.Gutsche,C.D.Calixarenes Revised,Royal Society of Chemistry,Cambridge,UK,1998,vol.6.
6.Afari,Z.;Bohmer,V.;Harrowfield,J.;Vicens,J.,(Eds.).Calixarenes 2001.Kluwer Acad.Publ.:Dordrecht.2001.
7.Beinert,H.B.;Holm,R.H.;Munck,E.Science.1997,277,653.
8.Lhotak,P.Top.Curr.Chem.2005,255,65.
9.Lee,S.H.;Kim,S.H.;Kim,S.K.;Jung,J.H.;Kim,J.S.J.Org.Chem.2005,70,9288.
10.Chen,Yuan-Yin,Zhang,Chun-Lei,Gong,Shu-Ling.Chinese Journal of Organic Chemistry.2007,27,795-805.
11.Lehn,J.M.Supramolecular Chemistry-Concepts and Perspectives,VCH,Weinheim,Germany,1995.
12.Atwood,J.L.;Davies,J.E.;Macnicol,D.D.;Vogtle,.F.;Lehn,J.M. Comprehensive Supramolecular Chemistry,Pergamon,1996.
13.Beer,E D.;Keefe,A.D.;Drew,M.G.B.J.Orgmet.Chem.1988,353,C10.
14.Beer,P D.;Keefe,A.D.;Slawin,A.M.Z.;Williams,D.J.J.Chem.Soc.,Dalton Trans.1990,3675.
15.Beer,E D.;Chen,Z.;Drew,M.G.B.;Gale,E A.J.Chem.Soc.,Chem.Commun.1995,1851.
16.Beer,P.D.;Gale,P.A.;Chen,Z.;Drew,M.G.B.Supramol.Chem.1996,7,241.
17.Beer,P.D.;Chen,Z.;Goulden,A.J.;Graydon,A.;Stokes,S.E.;Wear,T.J.Chem.Sot.,Chem.Commun.1993,1834.
18.Gale,P.A.;Chen,Z.;Drew,M.G.B.;Heath,J.A.;Beer,P.D.Polyhedron,1998,17,405.
19.Evans,A.J.;Matthews,S.E.;Cowley,A.R.;Beer,E D.J.Chem.Sot.,Dalton Trans.2003,4644.
20.Tomapatanaget,B.;Tuntulani,T.Tetrahedron Lett.2001,42,8105.
21.Tomapatanaget,B.;Tuntulani,T.Org.Lett.2003,5,1539.
22.Brindley,G.D.;Fox,O.D.;Beer,P.D.J.Chem.Soc.,Dalton Trans.2000,4354.
23.Cooper,J.B.;Drew,M.G.B.;Beer,P.D.J.Chem.Sot.,Dalton Trans.2000,2721.
24.Evans,A.J.;Beer,P.D.J.Chem.Soe.,Dalton Trans.2003,4451.
25.高永宏,硕士学士论文,山东师范大学,济南,2006.
26.张晓玲,硕士学士论文,山东师范大学,济南,2007.
27.Beer,P.D.;Keefe,A.D.J.Organomet.Chem.1989,375,C40.
28.Beer,P.D.;Hayes,E.J.Coord.Chem.Rev.2003,240,167.
29.(a)Beer,P.D.;Keefe,A.D.;Drew,M.G.B.J.Orgmet.Chem.1989,378,437.(b)Beer,P.D.Chem.Commun.1996,689.
30.Chung,T.D.;Kim,H.J.Incl.Phenom.Mol.Recognit.Chem.,1998,32,179.
31.(a)Reddy,P.A.;Kashyap,R.P.;Watson,W.M.;Gutsche,C.D.Isr.J.Chem.1992,32,89.(b)Beer,P.D.;Chen,Z.;Gale,P.A.Tetrahedron 1994,50,931.(c)Chung,T.D.;Park,J.;Kim,J.;Lim,H.;Choi,M.-J.;Kim,J.R.;Chang,S.-K.;Kim,H.Anal Chem.2001,73,3975.(d)Kerdpaiboon,N.;Tomapatanaget,B.;Chailapakul, O.; Tuntulani, T. J. Org. Chem. 2005, 70, 4797. (e) Webber, P. R. A.; Beer, P. D.; Chen, G. Z.; Felix, V.; Drew, M. G. B. J. Am. Chem. Soc. 2003, 125, 5774. (f) - Michael, D.; Lankshear; Andrew, R.; Cowley; Beer, P. D. Chem. Commun. 2006, 612.
32. (a) Nam, K. C.; Kang, S. O.; Jeong, H. S.; Jeon, S. Tetrahedron Lett. 1999, 40, 7343. (b) Jeong, H.; Choi, E. M.; Kang, S. O.; Nam, K. C; Jeon. S. J. Electroana. Chem. 2000, 485, 154. (c) Ki, Y. J.; Kang, S. O.; Cho, E. J.; Jeon, S.; Nam, K. C. Bull. Korean Chem. Soc. 2000, 21, 1152. (d) Cho, E. J.; Hwang, S. S.; Oh, J. ML; Kyoung, L. H.; Jeon, S.; Nam, K. C. Bull. Korean Chem. Soc. 2001, 22, 782. (e) Kang, S. O.; Oh, J. M.; Yang, Y. S.; Chun, J. C.; Jeon, S.; Nam, K. C. Bull. Korean Chem. Soc. 2002,23,145. (f) Yang, Y.-S.; Ko, S. W.; Song, I.-H.; Ryu, B. J.; Nam, K. C. Bull. Korean Chem. Soc. 2003,24,681.
33. Beer, P. D.; Chen, Z.; Goulden, A. J.; Grieve, A.; Hesek, D.; Szemes, F.; Wear, T. J. Chem. Soc, Chem. Commun. 1994, 1269.
34. Szemes, F.; Hesek, D.; Chen, Z.; Dent, S. W.; Drew, M. G. B.; Goulden, A. J.; Graydon, A. R.; Grieve, A.; Mortimer, R. J.; Wear, T.; Weightman, J. S.; Beer, P. D. Inorg. Chem. 1996, 35, 5868.
35. Trippe, G.; Derf, F. L.; Lyskawa, J.; Mazari, M.; Roncali, J.; Gorgues, A.; Levillain, E.; Salle, M. Chem. Eur. J. 2004,10, 6497.
36. Lyskawa, J.; Derf, R L.; Levillain, E.; Mazari, M.; Salle, M.; Dubois, L.; Viel, P.; Bureau, C.; Palacin, S. J. Am. Chem. Soc. 2004,126,12194.
37. Gorgues, A.; Hudhomme, P.; Salle, M. Chem. Rev. 2004,104, 5151.
38. Nielsen, K. A.; Jeppesen, J. O.; Levillain, E.; Becher, J. Angew. Chem., Int. Ed. 2003,42,187.
39. Nielsen, K. A.; Cho, W.-S.; Jeppesen, J. O.; Lynch, V. M.; Becher, J.; Sessler, J. L. J. Am. Chem. Soc. 2004,126, 16296.
40. Regnouf-de-Vains, J.-B.; Salle, M.; Lamartine, R. J. Chem. Soc, Perkin Trans. 2 1997,2461.
41. Zhao, B.-T.; Blesa, M.-J.; Mercier, N.; Derf, F. L.; Salle, M. J. Org. Chem. 2005, 70,6254.
42.Zhao,B.-T.;Blesa,M.-J.;Mercier,N.;Derf,F.L.;Salle,M.New J.Chem.2005,29,1164.
43.Chen,-Z.;Gale,P.A.;Beer,P.D.J.Electroana.Chem.1995,393,113.
44.Sun,X.-Y.;Chan,C.-S.;Wong,M.-S.;Wong,W.-Y.Tetrahedron 2006,62,7846.
45.Kim,J.S.;Lee,S.H.;Kim,S.H.;Kim,S.K.;Jung,J.H.J.Org.Chem.2005,70,9288.
46.Bernard,V.Molecular Fluorescence:Principles and Applications,Wiley-VCH Verlag GmbH,New York,2001,273-350.
47.Su.M.;Liu.Y.;Ma.H.;Ma.Q.;Wang.Z.;Yang.J.;Wang.M.Chem.Commute.2001,11,960-961.
48.Ma.H.;Jarzak.U.;Thiemann.W.NewJ.Chem.2001,25,872-874.
49.Kim J.S.,Quang.,D.T.Chem.Rev.2007,107,3780-3799
50.Leray,I.;Valeur,B.;O'Reilly,F.;Jiwan,J.L.H.;Soumillion,J.P.;Valeur,B.Chem.Commun.1999,795.
51.Leray,I.;Metivier,R.;Valeur,B.Chem.Commun.2003,996.
52.Leray,I.;Metivier,R.;Valeur,B.Chem.Eur.J.2004,10,4480.
53.Kim,J.S.;Bok,J.H.;Kim,H.J.;Lee,J.W.;Kim,S.K.;Choi,J.K.;Vicens,J.Tetrahedron Lett.2006,47,1237.
54.Huang,Z.-T.;Liu,J.M.;Zheng,Q.-Y.;Yang,J.-L.;Chen,C.-F.Tetrahedron Lett.2002,43,9209.
55.Chen,Q.-Y.;Chen,C.-F.Tetrahedron Lett.2005,46,165.
56.Diamond,D.;Perez-Jimenez,C.;Harris,S.J.J.Chem.Soc.,Chem.Commun.1993,480.
57.Vicens,J.;Unob,F.;Asfari,Z.Tetrahedron Lett.1998,39,2951-2954.
58.Kim,J.S.;Nob,K.H.;Lee,S.H.;Kim,S.K.;Kim,S.K.;Yoon,J.J.Org.Chem.2003,68,597.
59.Kim,J.S.;Yang,S.H.;Shon,O.J.;Park,K.M.;Lee,S.S.;Park,H.J.;Kim,M.J.;Lee,J.H.;Bull.Korean Chem.Soc.2002,23,1585.
60.(a)Dabestani,R.;Ji,H.F.;Brown,G.M.;Chem.Commun.1999,609.(b)Huang,Z.T.;Bu,J.H.;Zheng,Q.Y.;Chen,C.F.Org.Lett.2004,6,3301.(c)Jin,T. Chem. Commun. 1999, 2491. (d) Ji, H.-F.; Dabestani, R.; Brown, G. M.. J. Am. Chem. Soc. 2000,122,9306.
61. Kim, K. S.; Yoon, J.; Kim, S. K.; Singh, N. J. Chem. Soc. Rev. 2006, 35, 355.
62. Shinkai, S.; Aoki, I.; Kawabata, H.; Nakashima, K. J. Chem. Soc, Chem. Commun. 1991,1771.
63. Shinkai, S.; Matsumoto, H. Tetrahedron Lett. 1996,37,77.
64. Shinkai, S.; Aoki, I.; Sakaki, T.J. Chem. Soc, Chem. Commun. 1992, 730.
65. Kim, J. S.; Lee, J. Y.; Kim, S. K.; Jung, J. H. J. Org. Chem. 2005, 70,1463.
66. Kim, J. S.; Lee, S. H.; Kim, S. H.; Kim, S. K.; Jung, J. H. J. Org. Chem. 2005, 70, 9288.
67. Kim, J. S.; Lee, S. H.; Kim, J. Y.; Kim, S. K.; Lee, J. H. Tetrahedron. 2004, 60, 5171.
68. Kim, J. S.; Kim, S. H.; Choi, J. K.; Kim, S. K.; Sim, W. Tetrahedron Lett. 2006, 47, 3737.
69. Kim, J. S.; Choi, J. K.; Kim, S. H.; Yoon, J.; Lee, K.-H.; Bartsch, R. A. J. Org. Chem. 2006,71,8011.
70. Kim, J. S.; Kim, S. K.; Kim, S. H.; Kim, H. J.; Lee, S. H.; Lee, S. W.; Ko, J.; Bartsch, R. A. Inorg. Chem. 2005,44, 7866.
71. Kim, S. K.; Lee, S. H.; Lee, J. Y; Lee, J. Y; Bartsch, R. A.; Kim, J. S. J. Am. Chem. Soc 2004,126,16499
72. Bodenant, B.; Weil, T.; Businelli-Pourcel, M.; Fages, F.; Barbe, B.; Pianet, I.; Laguerre, M. J. Org. Chem. 1999, 64, 7034.
73. Reinhoudt, D. N.; van der Veen, N. J.; Flink, S.; Deij, M. A.; Egberink, R. J. M; van Veggel, F. C. J. M.; J. Am. Chem. Soc 2000,122, 6112
74. Kim, J. S.; Shon, O. J.; Rim, J. A.; Kim, S. K.; Yoon, J. J. Org. Chem. 2002, 67, 2348.
75. Diamond, D.; Schazmann, B.; Alhashimy, N. J. Am. Chem. Soc. 2006,128, 8607.
76. Zhang, H.; Han, L. F.; Zachariasse, K. A.; Jiang, Y. B. Org.Lett. 2005, 7, 4217.
77. Farruggia, G.; Iotti, S.; Prodi, L.; Montalti, M.; Zaccheroni, N.; Savage, P. B.; Trapani, V.; Sale, P.; Wolf, F. J. Am. Chem. Soc. 2006,128, 344.
78.Chen,C.H.;Shi,J.M.Coord.Chem.Rev.1998,171,161.
79.Tang,C.W.;VanSlyke,S.A.Appl.Phys.Lett.1987,51,913.
80.Toma,H.E.;Bagatin,I.A.New J.Chem.2000,24,841.
81.Toma,H.E.;Legnani,C.;Reyes,R.;Cremona,M.;Bagatin,I.A.Appl.Phys.Lett.2004,85,10.
82.Casnati,A.;Sansone,F.;Sartori,A.;Prodi,L.;Montalti,M.;Zaccheroni,N.;Ugozzoli,F.;Ungaro,R.Eur.J Org.Chem.2003,1475.
83.Chen,Y.Y.;Zhang,C.L.;Gong,S.L.;Luo,Z.Y.;Wu,X.J.Supramol.Chem.2006,18,483.
84.He,Y.B.;Huang,H.;Meng,L.Z.;Wu,C.T.;Yu,T.X.Chem.Lett.1999,1329.
85.Loffler,F.;Luning,U.;Gohar,G.New J.Chem.2000,24,935.
86.Leray,I.;Asfari,Z.;Vicens,J.;Valeur,B.J.Chem.Soc.,Perkin Trans.2 2002,1429.
87.Leray,I.;Malval,J.P.;Valeur,B.New J.Chem.2005,29,1089.
88.(a)Sharpless,K.B.;Lewis,W.G.;Green,L.G.;Finn,M.G.Angew.Chem.,Int.Ed.2002,41,1053.(b)Sharpless,K.B.;Rostovtsev,;V.V.;Green,L.G.;Fokin,V.V.Angew.Chem.,Int.Ed.2002,41,2596.(c)Sharpless,K.B.;Chan,T.R.;Robert,H.;Fokin,V.V.Org.Lett.2004,6,2853.
89.(a)Moorhouse,A.D.;Santos,A.M.;Gunaratnam,M.;Moore,M.;Neidle,S.;Moses,J.E.J.Am.Chem.Soe.2006,128,15972-15973.(b)Burley,G.A.;Gierlich,J.;Mofid,M.R.;Nir,H.;Tal,S.;Eichen,Y.;Carell,T.J.Am.Chem.Soc.2006,128,1398-1399.(c)Helms,B.;Mynar,J.L.;Hawker,C.J.;Frechet,J.M.J.J.Am.Chem.Soc.2004.126,15020-15021.(d)Rozkiewicz,D.I.;Janczewski,D.;Verboom,W.;Ravoo,B.J.;Reinhoudt,D.N.Angew.Chem.,Int.Ed.2006,45,5292-5296.
1.Steed,J.W.;Atwood,J.L.Supramolecular chemistry;John Wiley& Sons:New York.2000,pp.197-249.
2.(a)Kim,J.S.;Quang,D.T.Chem.Rev.2007,107,3780-3799.(b)Beer,P.D.;Gale,P.A.Angew.Chem.Int.Ed.2001,40,486-516.
3.(a)Kuo,L.-J.;Liao,J.-H.;Chen,C.-T.;Huang,C.-H.;Chen,C.-S.;Fang,J.-M.Org.Lett.2003,5,1821-1824.(b)Stone,D.L.;Smith,D.K.;McGrail,P.T.;J.Am.Chem.Soc.2002,124,856-864.(c)Beer,P.D.;Chen,G.Z.;Goulden,A.J.;Graydon,A.;Stoke,S.E.;Wear,T.J.Chem.Soc.,Chem.Commun.1993,1834-1836.(d)Tomapatanaget,B.;Tuntulani,T.;Chailapakul,O.Org.Lett.2003,5,1539-1542.
4.(a)Evans,A.J.;Matthews,S.E.;Cowley,A.R.;Beer,P.D.;Dalton Trans.2003,4644-4650.(b)Oton,F.;Tairraga,A.;Velasco,M.D.;Molina,P.Dalton Trans.2005,1159-1161.(c)Oton,F.;Tarraga,A.;Espinosa,A.;Velasco,M.D.;Molina,P.J.Org.Chem.2006,71,4590-4598.
5.(a)Beer,P.D.;Drew,M.G.B.;Smith,D.K.;J.Organomet.Chem.1997,543,259-261.(b)Beyer,L.;Richter,R.;Seidelmann,O.J.Organomet.Chem.1998,561,199-201.
6.(a)Beer,P.D.;Keefe,A.D.;Drew,M.G.B.J.Organomet.Chem.1988,353,C10-C12.(b)Murashima,T.;Tsukiyama,S.;Fujii,S.;Hayata,K.;Sakai,H.;Miyazawa,T.;Yamada,T.;Org.Biomol.Chem.2005,3,4060-4064.
7.(a)Sharpless,K.B.;Kolb,H.C.;Finn,M.G Angew.Chem.,lnt.Ed.2001,40,2004.(b)Sharpless,K.B.;Lewis,W.G.;Green,L.G.;Finn,M.G.Angew.Chem., Int.Ed 2002,41,1053.(c)Sharpless,K.B.;Rostovtsev,V.V.;Green,L.G.;Fokin,V.V.Angew.Chem.,Int.Ed.2002,41,2569.(d)Sharpless,K.B.;Chan,T.R.;Robert,H.;Fokin,V.V.Org.Lett.2004,6,2853.
8.(a)Moorhouse,A.D.;Santos,A.M.;Gunaratnam,M.;Moore,M.;Neidle,S.;Moses,J.E.J.Am.Chem.Soc.2006,128,15972-15973.(b)Burley,G.A.;Gierlich,J.;Mofid,M.R.;Nir,H.;Tal,S.;Eichen,Y.;Carell,T.J.Am.Chem.Soc.2006,128,1398-1399.(c)Helms,B.;Mynar,J.L.;Hawker,C.J.;Frechet,J.M.J.J.Am.Chem.Soc.2004.126,15020-15021.(d)Rozkiewicz,D.I.;Janczewski,D.;Verboom,W.;Ravoo,B.J.;Reinhoudt,D.N.Angew.Chem.,Int.Ed 2006,45,5292-5296.(f)Catia,O.;Jaime,R.A.;Eric,C.;Sandra,A.;Didier,A.Angew.Chem.,Int.Ed.2007,46,872.
9.张晓玲,硕士学位论文,山东师范大学,济南,2007
10.Gutsche,C.D.;Dhawan,B.;Muthukrishnan,K.H.N,R.J.Am.Chem.Soc.1981,103,3782-3792.
11.Park,W.K.C.;Meunier,S.J.;Zanini,D.;Roy,R.Carbohydr.Lett.1995,1,179-184.
12.(a)Nabeshima,T.;Saiki,T.;Iwabuchi,J.;Akine,S.J.Am.Chem.Soc.2005,127,5507-5511(b)Rosenblum,M.;Brawn,N.;Papenmeier,J.;Applebaum,M.J.Organomet.Chem.1966,6,173-180.
13.Jornoe,C.W.;Christensen,C.;Meldal,M.J.Org.Chem.2002,67,3057.
14.Li,Z.;Seo,T.S.;Ju,J.Tetrahedron Lett.2004,45,3143.
15.Huisgen,R.In 1,3-Dipolar Cycloaddition Chemistry Ed.:Padwa A.,Wiley,New York 1984,1-176.
16.Gothelf,K.V.;Jorgensen,K.;A.Chem.Rev.1998,98,863.
17.Najim,A.A.;Yaseen,A.A.;Asmehan,A.Heteroat.Chem.2004,15,380.
18.Gutsche,C.D.In Calixarenes,in Monographs in Supramolecular Chemistry,Ed.Stoddart,J.F.Royal Society of Chemistry London,1989.
19.Moon,K.;Kaifer,A.E.J.Am.Chem.Soc.2004,126,15016.
20.Saji,T.Chem.Lett.1986,275.
21.Plenio,H.;Aberle,C.Chem.Eur.J.2001,7,4438.
22.Bourgel,C.;Boyd,A.S.F.;Cooke,G.;deCremires,H.A.;Duclairoir,F.A.M.;Rot-ello,V.M.Chem.Commun.2001,1954.
23.Beer,P.D.;Gale,P.A.;Chen,G.Z.J.Chem.Soc.,Dalton Trans.1999,1897.
24.Beer,P.D.;Danks,J.P.;Hesek,D.;McAleer,J.F.J.Chem.Soc.Chem.Commun.1993,1735.
25.(a)Beer,P.D.;Chen,Z.;Goulden,A.J.;Graydon,A.R.;Stokes,S.E.;Wear,T.J.Chem.Soc.Chem.Commun.1993,1834.(b)Beer,P.D.;Graydon,A.R.;Johnson,A.O.M.;Smith,D.K.Inorg.Chem.1997,36,2112.
26.Beer,P.D.;Pratt,M.D.Polyhedron.2003,22,649.
27.Sohn,Y.S.;Hendrickson,D.N.;Gray,H.B.;J.Am.Chem.Soc.1971,93,3603-3612.
28.Beer,P.D.;Chen,Z.;Drew,M.G.B.;Johnson,A.O.M.;Smith,D.K.;Spencer,P.Inorg.Chem.Acta.1996,246,143-150.
1.(a)Beer,P.D.;Webber,P.R.A.;Chen,G.Z.;Felix,V.;Drew,M.G.B.J..Am.Chem.Soc.2003,125,5774.(b)Nielsen,K.A.;Jeppesen,J.O.;Levillain,E.;Becher,J.Angew.Chem.,Int.Ed.2003,42,187.(c)Lyskawa,J.;Derf,F.L.;Levillain,E.;Mazari,M.;Salle,M.;Dubois,L.;Viel,P.;Bureau,C.;Palacin,S.J.Am.Chem.Soc.2004,126,12194.(d)Zhao,B.-T.;Blesa,M.J.;Mercier,N.;Derf,F.L.;Salle,M.J.Org.Chem.2005,70,6254.
2.Kim,J.S.;Quang,D.T.Chem.Rev.2007,107,3780.
3.Chen,Q.-Y.;Chen,C.-F.Tetrahedron Lett.2005,46,165.
4.Kim,J.S.;Bok,J.H.;Kim,H.J.;Lee,J.W.;Kim,S.K.;Choi,J.K.;Vicens,J.Tetrahedron Lett.2006,47,1237.
5.Reinhoudt,D.N.;van der Veen,N.J.;Flink,S.;Deij,M.A.;Egberink,R.J.M.;van Veggel,F.C.J.M.;J.Am.Chem.Soc.2000,122,6112.
6.Leray,I.;Metivier,R.;Valeur,B.Chem.Commun.2003,996.
7.Diamond,D.;Schazmann,B.;Alhashimy,N.J.Am.Chem.Soc.2006,128,8607.
8.(a)Sharpless,K.B.;Lewis,W.G.;Green,L.G.;Finn,M.G.Angew.Chem.,Int.Ed 2002,41,1053.(b)Sharpless,K.B.;Rostovtsev,V.V.;Green,L.G.;Fokin, V. V. Angew. Chem., Int. Ed. 2002, 41, 2569. (c) Sharpless, K. B.; Chan, T. R.; Robert, H.; Fokin, V. V. Org. Lett. 2004,6,2853.
9. Farruggia, G.; Iotti, S.; Prodi, L.; Montalti, M.; Zaccheroni, N.; Savage, P. B.; Trapani, V.; Sale, P.; Wolf, F. J. Am. Chem. Soc. 2006,128, 344.
10. Torn(?)e, C. W,; Christensen, C; Meldal, M. J. Org. Chem. 2002, 67, 3057.
11. Li, Z.; Seo T. S.; Ju, J. Tetrahedron Lett. 2004,45, 3143.
12. Jaime, C.; Mendoza, J; Prados, P.; Nieto, P. M.; Sanchez, C. J. Org. Chem., 1991, 56, 3372.
13. Iwamoto, K.; Araki, K.; Shinkai, S. J. Org. Chem. 1991,56,4955.
14. Gutsche, C. D.; Dhawan, B.; No, K. H.; Muthukrishnan, R. J. Am. Chem. Soc. 1981,103, 3782.
15. Toma, H. E.; Bagatin, I. A. New. J. Chem. 2000,24, 841.
16. Unob, F.; Asfari, Z.; Vicens, J. Tetrahedron Lett. 1998, 39, 2951.
17. Chen, Y. Y.; Zhang, C. L.; Gong, S. L.; Luo, Z. Y; Wu, X. J. Supramol. Chem. 2006,18,483.
18. Gutsche, C. D.; Iqbal, M. Org. Synth. 1990, 68, 234.
19. Nabeshima, T.;.Saiki, T.; Iwabuchi, J.; Akine, S. J. Am. Chem. Soc. 2005, 127, 5507.
20. Jose, G.; Rodriguze, J. G.; Antonio, O.; Rosa, M. M. J. Orgmet. Chem. 1996, 513, 71.
2.Gutsche,C.D.In Calixarenes,in Monographs in Supramolecular Chemistry,Ed.Stoddart,J.F.Royal Society of Chemistry,London,1989.
3.Bohemer,V.Angew.Chem.,Int.Ed.Engl.1995,34,715.
4.Takeshita,M.;Shinkai,S.Chem.Soc.Jpn.1995,68,1088.
5.Gutsche,C.D.Calixarenes Revised,Royal Society of Chemistry,Cambridge,UK,1998,vol.6.
6.Afari,Z.;Bohmer,V.;Harrowfield,J.;Vicens,J.,(Eds.).Calixarenes 2001.Kluwer Acad.Publ.:Dordrecht.2001.
7.Beinert,H.B.;Holm,R.H.;Munck,E.Science.1997,277,653.
8.Lhotak,P.Top.Curr.Chem.2005,255,65.
9.Lee,S.H.;Kim,S.H.;Kim,S.K.;Jung,J.H.;Kim,J.S.J.Org.Chem.2005,70,9288.
10.Chen,Yuan-Yin,Zhang,Chun-Lei,Gong,Shu-Ling.Chinese Journal of Organic Chemistry.2007,27,795-805.
11.Lehn,J.M.Supramolecular Chemistry-Concepts and Perspectives,VCH,Weinheim,Germany,1995.
12.Atwood,J.L.;Davies,J.E.;Macnicol,D.D.;Vogtle,.F.;Lehn,J.M. Comprehensive Supramolecular Chemistry,Pergamon,1996.
13.Beer,E D.;Keefe,A.D.;Drew,M.G.B.J.Orgmet.Chem.1988,353,C10.
14.Beer,P D.;Keefe,A.D.;Slawin,A.M.Z.;Williams,D.J.J.Chem.Soc.,Dalton Trans.1990,3675.
15.Beer,E D.;Chen,Z.;Drew,M.G.B.;Gale,E A.J.Chem.Soc.,Chem.Commun.1995,1851.
16.Beer,P.D.;Gale,P.A.;Chen,Z.;Drew,M.G.B.Supramol.Chem.1996,7,241.
17.Beer,P.D.;Chen,Z.;Goulden,A.J.;Graydon,A.;Stokes,S.E.;Wear,T.J.Chem.Sot.,Chem.Commun.1993,1834.
18.Gale,P.A.;Chen,Z.;Drew,M.G.B.;Heath,J.A.;Beer,P.D.Polyhedron,1998,17,405.
19.Evans,A.J.;Matthews,S.E.;Cowley,A.R.;Beer,E D.J.Chem.Sot.,Dalton Trans.2003,4644.
20.Tomapatanaget,B.;Tuntulani,T.Tetrahedron Lett.2001,42,8105.
21.Tomapatanaget,B.;Tuntulani,T.Org.Lett.2003,5,1539.
22.Brindley,G.D.;Fox,O.D.;Beer,P.D.J.Chem.Soc.,Dalton Trans.2000,4354.
23.Cooper,J.B.;Drew,M.G.B.;Beer,P.D.J.Chem.Sot.,Dalton Trans.2000,2721.
24.Evans,A.J.;Beer,P.D.J.Chem.Soe.,Dalton Trans.2003,4451.
25.高永宏,硕士学士论文,山东师范大学,济南,2006.
26.张晓玲,硕士学士论文,山东师范大学,济南,2007.
27.Beer,P.D.;Keefe,A.D.J.Organomet.Chem.1989,375,C40.
28.Beer,P.D.;Hayes,E.J.Coord.Chem.Rev.2003,240,167.
29.(a)Beer,P.D.;Keefe,A.D.;Drew,M.G.B.J.Orgmet.Chem.1989,378,437.(b)Beer,P.D.Chem.Commun.1996,689.
30.Chung,T.D.;Kim,H.J.Incl.Phenom.Mol.Recognit.Chem.,1998,32,179.
31.(a)Reddy,P.A.;Kashyap,R.P.;Watson,W.M.;Gutsche,C.D.Isr.J.Chem.1992,32,89.(b)Beer,P.D.;Chen,Z.;Gale,P.A.Tetrahedron 1994,50,931.(c)Chung,T.D.;Park,J.;Kim,J.;Lim,H.;Choi,M.-J.;Kim,J.R.;Chang,S.-K.;Kim,H.Anal Chem.2001,73,3975.(d)Kerdpaiboon,N.;Tomapatanaget,B.;Chailapakul, O.; Tuntulani, T. J. Org. Chem. 2005, 70, 4797. (e) Webber, P. R. A.; Beer, P. D.; Chen, G. Z.; Felix, V.; Drew, M. G. B. J. Am. Chem. Soc. 2003, 125, 5774. (f) - Michael, D.; Lankshear; Andrew, R.; Cowley; Beer, P. D. Chem. Commun. 2006, 612.
32. (a) Nam, K. C.; Kang, S. O.; Jeong, H. S.; Jeon, S. Tetrahedron Lett. 1999, 40, 7343. (b) Jeong, H.; Choi, E. M.; Kang, S. O.; Nam, K. C; Jeon. S. J. Electroana. Chem. 2000, 485, 154. (c) Ki, Y. J.; Kang, S. O.; Cho, E. J.; Jeon, S.; Nam, K. C. Bull. Korean Chem. Soc. 2000, 21, 1152. (d) Cho, E. J.; Hwang, S. S.; Oh, J. ML; Kyoung, L. H.; Jeon, S.; Nam, K. C. Bull. Korean Chem. Soc. 2001, 22, 782. (e) Kang, S. O.; Oh, J. M.; Yang, Y. S.; Chun, J. C.; Jeon, S.; Nam, K. C. Bull. Korean Chem. Soc. 2002,23,145. (f) Yang, Y.-S.; Ko, S. W.; Song, I.-H.; Ryu, B. J.; Nam, K. C. Bull. Korean Chem. Soc. 2003,24,681.
33. Beer, P. D.; Chen, Z.; Goulden, A. J.; Grieve, A.; Hesek, D.; Szemes, F.; Wear, T. J. Chem. Soc, Chem. Commun. 1994, 1269.
34. Szemes, F.; Hesek, D.; Chen, Z.; Dent, S. W.; Drew, M. G. B.; Goulden, A. J.; Graydon, A. R.; Grieve, A.; Mortimer, R. J.; Wear, T.; Weightman, J. S.; Beer, P. D. Inorg. Chem. 1996, 35, 5868.
35. Trippe, G.; Derf, F. L.; Lyskawa, J.; Mazari, M.; Roncali, J.; Gorgues, A.; Levillain, E.; Salle, M. Chem. Eur. J. 2004,10, 6497.
36. Lyskawa, J.; Derf, R L.; Levillain, E.; Mazari, M.; Salle, M.; Dubois, L.; Viel, P.; Bureau, C.; Palacin, S. J. Am. Chem. Soc. 2004,126,12194.
37. Gorgues, A.; Hudhomme, P.; Salle, M. Chem. Rev. 2004,104, 5151.
38. Nielsen, K. A.; Jeppesen, J. O.; Levillain, E.; Becher, J. Angew. Chem., Int. Ed. 2003,42,187.
39. Nielsen, K. A.; Cho, W.-S.; Jeppesen, J. O.; Lynch, V. M.; Becher, J.; Sessler, J. L. J. Am. Chem. Soc. 2004,126, 16296.
40. Regnouf-de-Vains, J.-B.; Salle, M.; Lamartine, R. J. Chem. Soc, Perkin Trans. 2 1997,2461.
41. Zhao, B.-T.; Blesa, M.-J.; Mercier, N.; Derf, F. L.; Salle, M. J. Org. Chem. 2005, 70,6254.
42.Zhao,B.-T.;Blesa,M.-J.;Mercier,N.;Derf,F.L.;Salle,M.New J.Chem.2005,29,1164.
43.Chen,-Z.;Gale,P.A.;Beer,P.D.J.Electroana.Chem.1995,393,113.
44.Sun,X.-Y.;Chan,C.-S.;Wong,M.-S.;Wong,W.-Y.Tetrahedron 2006,62,7846.
45.Kim,J.S.;Lee,S.H.;Kim,S.H.;Kim,S.K.;Jung,J.H.J.Org.Chem.2005,70,9288.
46.Bernard,V.Molecular Fluorescence:Principles and Applications,Wiley-VCH Verlag GmbH,New York,2001,273-350.
47.Su.M.;Liu.Y.;Ma.H.;Ma.Q.;Wang.Z.;Yang.J.;Wang.M.Chem.Commute.2001,11,960-961.
48.Ma.H.;Jarzak.U.;Thiemann.W.NewJ.Chem.2001,25,872-874.
49.Kim J.S.,Quang.,D.T.Chem.Rev.2007,107,3780-3799
50.Leray,I.;Valeur,B.;O'Reilly,F.;Jiwan,J.L.H.;Soumillion,J.P.;Valeur,B.Chem.Commun.1999,795.
51.Leray,I.;Metivier,R.;Valeur,B.Chem.Commun.2003,996.
52.Leray,I.;Metivier,R.;Valeur,B.Chem.Eur.J.2004,10,4480.
53.Kim,J.S.;Bok,J.H.;Kim,H.J.;Lee,J.W.;Kim,S.K.;Choi,J.K.;Vicens,J.Tetrahedron Lett.2006,47,1237.
54.Huang,Z.-T.;Liu,J.M.;Zheng,Q.-Y.;Yang,J.-L.;Chen,C.-F.Tetrahedron Lett.2002,43,9209.
55.Chen,Q.-Y.;Chen,C.-F.Tetrahedron Lett.2005,46,165.
56.Diamond,D.;Perez-Jimenez,C.;Harris,S.J.J.Chem.Soc.,Chem.Commun.1993,480.
57.Vicens,J.;Unob,F.;Asfari,Z.Tetrahedron Lett.1998,39,2951-2954.
58.Kim,J.S.;Nob,K.H.;Lee,S.H.;Kim,S.K.;Kim,S.K.;Yoon,J.J.Org.Chem.2003,68,597.
59.Kim,J.S.;Yang,S.H.;Shon,O.J.;Park,K.M.;Lee,S.S.;Park,H.J.;Kim,M.J.;Lee,J.H.;Bull.Korean Chem.Soc.2002,23,1585.
60.(a)Dabestani,R.;Ji,H.F.;Brown,G.M.;Chem.Commun.1999,609.(b)Huang,Z.T.;Bu,J.H.;Zheng,Q.Y.;Chen,C.F.Org.Lett.2004,6,3301.(c)Jin,T. Chem. Commun. 1999, 2491. (d) Ji, H.-F.; Dabestani, R.; Brown, G. M.. J. Am. Chem. Soc. 2000,122,9306.
61. Kim, K. S.; Yoon, J.; Kim, S. K.; Singh, N. J. Chem. Soc. Rev. 2006, 35, 355.
62. Shinkai, S.; Aoki, I.; Kawabata, H.; Nakashima, K. J. Chem. Soc, Chem. Commun. 1991,1771.
63. Shinkai, S.; Matsumoto, H. Tetrahedron Lett. 1996,37,77.
64. Shinkai, S.; Aoki, I.; Sakaki, T.J. Chem. Soc, Chem. Commun. 1992, 730.
65. Kim, J. S.; Lee, J. Y.; Kim, S. K.; Jung, J. H. J. Org. Chem. 2005, 70,1463.
66. Kim, J. S.; Lee, S. H.; Kim, S. H.; Kim, S. K.; Jung, J. H. J. Org. Chem. 2005, 70, 9288.
67. Kim, J. S.; Lee, S. H.; Kim, J. Y.; Kim, S. K.; Lee, J. H. Tetrahedron. 2004, 60, 5171.
68. Kim, J. S.; Kim, S. H.; Choi, J. K.; Kim, S. K.; Sim, W. Tetrahedron Lett. 2006, 47, 3737.
69. Kim, J. S.; Choi, J. K.; Kim, S. H.; Yoon, J.; Lee, K.-H.; Bartsch, R. A. J. Org. Chem. 2006,71,8011.
70. Kim, J. S.; Kim, S. K.; Kim, S. H.; Kim, H. J.; Lee, S. H.; Lee, S. W.; Ko, J.; Bartsch, R. A. Inorg. Chem. 2005,44, 7866.
71. Kim, S. K.; Lee, S. H.; Lee, J. Y; Lee, J. Y; Bartsch, R. A.; Kim, J. S. J. Am. Chem. Soc 2004,126,16499
72. Bodenant, B.; Weil, T.; Businelli-Pourcel, M.; Fages, F.; Barbe, B.; Pianet, I.; Laguerre, M. J. Org. Chem. 1999, 64, 7034.
73. Reinhoudt, D. N.; van der Veen, N. J.; Flink, S.; Deij, M. A.; Egberink, R. J. M; van Veggel, F. C. J. M.; J. Am. Chem. Soc 2000,122, 6112
74. Kim, J. S.; Shon, O. J.; Rim, J. A.; Kim, S. K.; Yoon, J. J. Org. Chem. 2002, 67, 2348.
75. Diamond, D.; Schazmann, B.; Alhashimy, N. J. Am. Chem. Soc. 2006,128, 8607.
76. Zhang, H.; Han, L. F.; Zachariasse, K. A.; Jiang, Y. B. Org.Lett. 2005, 7, 4217.
77. Farruggia, G.; Iotti, S.; Prodi, L.; Montalti, M.; Zaccheroni, N.; Savage, P. B.; Trapani, V.; Sale, P.; Wolf, F. J. Am. Chem. Soc. 2006,128, 344.
78.Chen,C.H.;Shi,J.M.Coord.Chem.Rev.1998,171,161.
79.Tang,C.W.;VanSlyke,S.A.Appl.Phys.Lett.1987,51,913.
80.Toma,H.E.;Bagatin,I.A.New J.Chem.2000,24,841.
81.Toma,H.E.;Legnani,C.;Reyes,R.;Cremona,M.;Bagatin,I.A.Appl.Phys.Lett.2004,85,10.
82.Casnati,A.;Sansone,F.;Sartori,A.;Prodi,L.;Montalti,M.;Zaccheroni,N.;Ugozzoli,F.;Ungaro,R.Eur.J Org.Chem.2003,1475.
83.Chen,Y.Y.;Zhang,C.L.;Gong,S.L.;Luo,Z.Y.;Wu,X.J.Supramol.Chem.2006,18,483.
84.He,Y.B.;Huang,H.;Meng,L.Z.;Wu,C.T.;Yu,T.X.Chem.Lett.1999,1329.
85.Loffler,F.;Luning,U.;Gohar,G.New J.Chem.2000,24,935.
86.Leray,I.;Asfari,Z.;Vicens,J.;Valeur,B.J.Chem.Soc.,Perkin Trans.2 2002,1429.
87.Leray,I.;Malval,J.P.;Valeur,B.New J.Chem.2005,29,1089.
88.(a)Sharpless,K.B.;Lewis,W.G.;Green,L.G.;Finn,M.G.Angew.Chem.,Int.Ed.2002,41,1053.(b)Sharpless,K.B.;Rostovtsev,;V.V.;Green,L.G.;Fokin,V.V.Angew.Chem.,Int.Ed.2002,41,2596.(c)Sharpless,K.B.;Chan,T.R.;Robert,H.;Fokin,V.V.Org.Lett.2004,6,2853.
89.(a)Moorhouse,A.D.;Santos,A.M.;Gunaratnam,M.;Moore,M.;Neidle,S.;Moses,J.E.J.Am.Chem.Soe.2006,128,15972-15973.(b)Burley,G.A.;Gierlich,J.;Mofid,M.R.;Nir,H.;Tal,S.;Eichen,Y.;Carell,T.J.Am.Chem.Soc.2006,128,1398-1399.(c)Helms,B.;Mynar,J.L.;Hawker,C.J.;Frechet,J.M.J.J.Am.Chem.Soc.2004.126,15020-15021.(d)Rozkiewicz,D.I.;Janczewski,D.;Verboom,W.;Ravoo,B.J.;Reinhoudt,D.N.Angew.Chem.,Int.Ed.2006,45,5292-5296.
1.Steed,J.W.;Atwood,J.L.Supramolecular chemistry;John Wiley& Sons:New York.2000,pp.197-249.
2.(a)Kim,J.S.;Quang,D.T.Chem.Rev.2007,107,3780-3799.(b)Beer,P.D.;Gale,P.A.Angew.Chem.Int.Ed.2001,40,486-516.
3.(a)Kuo,L.-J.;Liao,J.-H.;Chen,C.-T.;Huang,C.-H.;Chen,C.-S.;Fang,J.-M.Org.Lett.2003,5,1821-1824.(b)Stone,D.L.;Smith,D.K.;McGrail,P.T.;J.Am.Chem.Soc.2002,124,856-864.(c)Beer,P.D.;Chen,G.Z.;Goulden,A.J.;Graydon,A.;Stoke,S.E.;Wear,T.J.Chem.Soc.,Chem.Commun.1993,1834-1836.(d)Tomapatanaget,B.;Tuntulani,T.;Chailapakul,O.Org.Lett.2003,5,1539-1542.
4.(a)Evans,A.J.;Matthews,S.E.;Cowley,A.R.;Beer,P.D.;Dalton Trans.2003,4644-4650.(b)Oton,F.;Tairraga,A.;Velasco,M.D.;Molina,P.Dalton Trans.2005,1159-1161.(c)Oton,F.;Tarraga,A.;Espinosa,A.;Velasco,M.D.;Molina,P.J.Org.Chem.2006,71,4590-4598.
5.(a)Beer,P.D.;Drew,M.G.B.;Smith,D.K.;J.Organomet.Chem.1997,543,259-261.(b)Beyer,L.;Richter,R.;Seidelmann,O.J.Organomet.Chem.1998,561,199-201.
6.(a)Beer,P.D.;Keefe,A.D.;Drew,M.G.B.J.Organomet.Chem.1988,353,C10-C12.(b)Murashima,T.;Tsukiyama,S.;Fujii,S.;Hayata,K.;Sakai,H.;Miyazawa,T.;Yamada,T.;Org.Biomol.Chem.2005,3,4060-4064.
7.(a)Sharpless,K.B.;Kolb,H.C.;Finn,M.G Angew.Chem.,lnt.Ed.2001,40,2004.(b)Sharpless,K.B.;Lewis,W.G.;Green,L.G.;Finn,M.G.Angew.Chem., Int.Ed 2002,41,1053.(c)Sharpless,K.B.;Rostovtsev,V.V.;Green,L.G.;Fokin,V.V.Angew.Chem.,Int.Ed.2002,41,2569.(d)Sharpless,K.B.;Chan,T.R.;Robert,H.;Fokin,V.V.Org.Lett.2004,6,2853.
8.(a)Moorhouse,A.D.;Santos,A.M.;Gunaratnam,M.;Moore,M.;Neidle,S.;Moses,J.E.J.Am.Chem.Soc.2006,128,15972-15973.(b)Burley,G.A.;Gierlich,J.;Mofid,M.R.;Nir,H.;Tal,S.;Eichen,Y.;Carell,T.J.Am.Chem.Soc.2006,128,1398-1399.(c)Helms,B.;Mynar,J.L.;Hawker,C.J.;Frechet,J.M.J.J.Am.Chem.Soc.2004.126,15020-15021.(d)Rozkiewicz,D.I.;Janczewski,D.;Verboom,W.;Ravoo,B.J.;Reinhoudt,D.N.Angew.Chem.,Int.Ed 2006,45,5292-5296.(f)Catia,O.;Jaime,R.A.;Eric,C.;Sandra,A.;Didier,A.Angew.Chem.,Int.Ed.2007,46,872.
9.张晓玲,硕士学位论文,山东师范大学,济南,2007
10.Gutsche,C.D.;Dhawan,B.;Muthukrishnan,K.H.N,R.J.Am.Chem.Soc.1981,103,3782-3792.
11.Park,W.K.C.;Meunier,S.J.;Zanini,D.;Roy,R.Carbohydr.Lett.1995,1,179-184.
12.(a)Nabeshima,T.;Saiki,T.;Iwabuchi,J.;Akine,S.J.Am.Chem.Soc.2005,127,5507-5511(b)Rosenblum,M.;Brawn,N.;Papenmeier,J.;Applebaum,M.J.Organomet.Chem.1966,6,173-180.
13.Jornoe,C.W.;Christensen,C.;Meldal,M.J.Org.Chem.2002,67,3057.
14.Li,Z.;Seo,T.S.;Ju,J.Tetrahedron Lett.2004,45,3143.
15.Huisgen,R.In 1,3-Dipolar Cycloaddition Chemistry Ed.:Padwa A.,Wiley,New York 1984,1-176.
16.Gothelf,K.V.;Jorgensen,K.;A.Chem.Rev.1998,98,863.
17.Najim,A.A.;Yaseen,A.A.;Asmehan,A.Heteroat.Chem.2004,15,380.
18.Gutsche,C.D.In Calixarenes,in Monographs in Supramolecular Chemistry,Ed.Stoddart,J.F.Royal Society of Chemistry London,1989.
19.Moon,K.;Kaifer,A.E.J.Am.Chem.Soc.2004,126,15016.
20.Saji,T.Chem.Lett.1986,275.
21.Plenio,H.;Aberle,C.Chem.Eur.J.2001,7,4438.
22.Bourgel,C.;Boyd,A.S.F.;Cooke,G.;deCremires,H.A.;Duclairoir,F.A.M.;Rot-ello,V.M.Chem.Commun.2001,1954.
23.Beer,P.D.;Gale,P.A.;Chen,G.Z.J.Chem.Soc.,Dalton Trans.1999,1897.
24.Beer,P.D.;Danks,J.P.;Hesek,D.;McAleer,J.F.J.Chem.Soc.Chem.Commun.1993,1735.
25.(a)Beer,P.D.;Chen,Z.;Goulden,A.J.;Graydon,A.R.;Stokes,S.E.;Wear,T.J.Chem.Soc.Chem.Commun.1993,1834.(b)Beer,P.D.;Graydon,A.R.;Johnson,A.O.M.;Smith,D.K.Inorg.Chem.1997,36,2112.
26.Beer,P.D.;Pratt,M.D.Polyhedron.2003,22,649.
27.Sohn,Y.S.;Hendrickson,D.N.;Gray,H.B.;J.Am.Chem.Soc.1971,93,3603-3612.
28.Beer,P.D.;Chen,Z.;Drew,M.G.B.;Johnson,A.O.M.;Smith,D.K.;Spencer,P.Inorg.Chem.Acta.1996,246,143-150.
1.(a)Beer,P.D.;Webber,P.R.A.;Chen,G.Z.;Felix,V.;Drew,M.G.B.J..Am.Chem.Soc.2003,125,5774.(b)Nielsen,K.A.;Jeppesen,J.O.;Levillain,E.;Becher,J.Angew.Chem.,Int.Ed.2003,42,187.(c)Lyskawa,J.;Derf,F.L.;Levillain,E.;Mazari,M.;Salle,M.;Dubois,L.;Viel,P.;Bureau,C.;Palacin,S.J.Am.Chem.Soc.2004,126,12194.(d)Zhao,B.-T.;Blesa,M.J.;Mercier,N.;Derf,F.L.;Salle,M.J.Org.Chem.2005,70,6254.
2.Kim,J.S.;Quang,D.T.Chem.Rev.2007,107,3780.
3.Chen,Q.-Y.;Chen,C.-F.Tetrahedron Lett.2005,46,165.
4.Kim,J.S.;Bok,J.H.;Kim,H.J.;Lee,J.W.;Kim,S.K.;Choi,J.K.;Vicens,J.Tetrahedron Lett.2006,47,1237.
5.Reinhoudt,D.N.;van der Veen,N.J.;Flink,S.;Deij,M.A.;Egberink,R.J.M.;van Veggel,F.C.J.M.;J.Am.Chem.Soc.2000,122,6112.
6.Leray,I.;Metivier,R.;Valeur,B.Chem.Commun.2003,996.
7.Diamond,D.;Schazmann,B.;Alhashimy,N.J.Am.Chem.Soc.2006,128,8607.
8.(a)Sharpless,K.B.;Lewis,W.G.;Green,L.G.;Finn,M.G.Angew.Chem.,Int.Ed 2002,41,1053.(b)Sharpless,K.B.;Rostovtsev,V.V.;Green,L.G.;Fokin, V. V. Angew. Chem., Int. Ed. 2002, 41, 2569. (c) Sharpless, K. B.; Chan, T. R.; Robert, H.; Fokin, V. V. Org. Lett. 2004,6,2853.
9. Farruggia, G.; Iotti, S.; Prodi, L.; Montalti, M.; Zaccheroni, N.; Savage, P. B.; Trapani, V.; Sale, P.; Wolf, F. J. Am. Chem. Soc. 2006,128, 344.
10. Torn(?)e, C. W,; Christensen, C; Meldal, M. J. Org. Chem. 2002, 67, 3057.
11. Li, Z.; Seo T. S.; Ju, J. Tetrahedron Lett. 2004,45, 3143.
12. Jaime, C.; Mendoza, J; Prados, P.; Nieto, P. M.; Sanchez, C. J. Org. Chem., 1991, 56, 3372.
13. Iwamoto, K.; Araki, K.; Shinkai, S. J. Org. Chem. 1991,56,4955.
14. Gutsche, C. D.; Dhawan, B.; No, K. H.; Muthukrishnan, R. J. Am. Chem. Soc. 1981,103, 3782.
15. Toma, H. E.; Bagatin, I. A. New. J. Chem. 2000,24, 841.
16. Unob, F.; Asfari, Z.; Vicens, J. Tetrahedron Lett. 1998, 39, 2951.
17. Chen, Y. Y.; Zhang, C. L.; Gong, S. L.; Luo, Z. Y; Wu, X. J. Supramol. Chem. 2006,18,483.
18. Gutsche, C. D.; Iqbal, M. Org. Synth. 1990, 68, 234.
19. Nabeshima, T.;.Saiki, T.; Iwabuchi, J.; Akine, S. J. Am. Chem. Soc. 2005, 127, 5507.
20. Jose, G.; Rodriguze, J. G.; Antonio, O.; Rosa, M. M. J. Orgmet. Chem. 1996, 513, 71.