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Frontiers of Chemistry in China

ISSN 1673-3495

ISSN 1673-3614(Online)

CN 11-5726/O6

Front. Chem. China    2010, Vol. 5 Issue (2) : 184-192    https://doi.org/10.1007/s11458-010-0109-5
Research articles
Zn 2+ cation triggers self-assembly of cyclen into a stable metallogel
Tianmin SHU,Junchen WU,Ying ZOU,Keyin LIU,Liqing CHEN,Tao YI,
Department of Chemistry and Laboratory of Advanced Materials, Fudan University, Shanghai 200433, China;
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Abstract A novel type of ligands contained 1,4,7,10-tetrazacyclododecane and functionalized by two azobenzene moieties grafted with two alkyl chains was designed and synthesized. The ligands with long alkyl chains can form metallogels in the presence of Zn2+ cations. The formation of metallogel was followed by NMR and electronic spectral detection. The morphology of the xerogels is varied with the equivalent of Zn2+ cations and the concentration of the gel. Spectral and structural analysis indicated that the driving forces of the gel formation were attributed to intermolecular hydrophobic interactions between alkyl chains and π-π interaction between azobenzenes.
Keywords cyclen      metallogel      self-assembly      azobenzene      
Issue Date: 05 June 2010
 Cite this article:   
Tianmin SHU,Junchen WU,Ying ZOU, et al. Zn 2+ cation triggers self-assembly of cyclen into a stable metallogel[J]. Front. Chem. China, 2010, 5(2): 184-192.
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https://academic.hep.com.cn/fcc/EN/10.1007/s11458-010-0109-5
https://academic.hep.com.cn/fcc/EN/Y2010/V5/I2/184
Lehn, J. M., Supramolecular Chemistry: Concepts and Perspectives; VCH: Weinheim, 1995
Steed, J. W.; Atwood, J. L., SupramolecularChemistry; Wiley: Chichester, 2000
Whitesides, G. M.; Simanek, E. E.; Mathias, J. P.; Seto, C. T.; Chin, D.; Mammen, M.; Gordon, D. M., Acc. Chem. Res. 1995, 28, 37―44

doi: 10.1021/ar00049a006
Philip, D.; Stoddart, J. F., Angew. Chem. Int. Ed. 1996, 35, 1155―1196
Piguet, C.; Bernardinelli, G.; Hopfgartner, G., Chem. Rev. 1997, 97, 2005―2062

doi: 10.1021/cr960053s
Holliday, B. J.; Mirkin, C. A., Angew. Chem. Int. Ed. 2001, 40, 2022―2043

doi: 10.1002/1521-3773(20010601)40:11<2022::AID-ANIE2022>3.0.CO;2-D
Prins, L. J.; Reinhoudt, D. N.; Timmerman, P., Angew. Chem. Int. Ed. 2001, 40, 2382―2426

doi: 10.1002/1521-3773(20010702)40:13<2382::AID-ANIE2382>3.0.CO;2-G
Cram, D. J., Angew. Chem. Int. Ed. 1998, 27, 1009―1020
Pedersen, C. J., Angew. Chem. Int. Ed. 1998, 27, 1021―1027
Himeda, Y.; Hiratani, K.; Kasuga, K.; Hirose, T., Chem. Lett. 1993, 9, 1475―1478

doi: 10.1246/cl.1993.1475
Gaikwad, A. G.; Noguchi, H.; Yoshio, M., Sep. Sci. Technol. 1991, 26, 853―867

doi: 10.1080/01496399108050501
Gasperov, V.; Lindoy, L. F.; Parkin, A.; Turner, P., J. Mol. Struct. 2007, 839, 132―136

doi: 10.1016/j.molstruc.2006.11.011
Develay, S.; Tripier, R.; Bernier, N.; Le Baccon, M.; Patinec, V.; Serratrice, G.; Handel, H., Dalton Trans. 2007, 1038―1046

doi: 10.1039/b616862k
Aoki, S.; Sakurama, K.; Matsuo, N.; Yamada, Y.; Takasawa, R.; Tanuma, S.; Shiro, M.; Takeda, K.; Kimura, E., Chem. Eur. J. 2006, 12, 9066―9080

doi: 10.1002/chem.200600379
Trivedi, D. R.; Dastidar, P., Cryst. Growth Des. 2006, 6, 2114―2121

doi: 10.1021/cg060325c
Hancock, R. D.; Dobson, S. M.; Evers, A.; Wade, P. W.; Ngwenya, M. P.; Boeyens, J. C. A.; Wainwright, K. P., J. Am. Chem. Soc. 1988, 110, 2788―2794

doi: 10.1021/ja00217a016
Hancock, R. D.; Wade, P. W.; Ngwenya, M. P.; De Sousa, A. S.; Damu, K. V., Inorg. Chem. 1990, 29, 1968―1974
Akkaya, E. U.; Huston, M. E.; Czarnik, A. W., J. Am. Chem. Soc. 1990, 112, 3590―3593

doi: 10.1021/ja00165a051
Kimura, E.; Koike, T.; Shionoya, M., Structure and Bonding: MetalSite in Proteins and Models; Springer: Berlin, 1997; Vol. 89,p 1―28
Kimura, E.; Koike, T., Chem. Commun. 1998, 1495―1500
Kimura, E.; Kikuta, E., J. Biol. Inorg. Chem. 2000, 5, 139―155

doi: 10.1007/s007750050359
Kimura, E.; Aoki, S., Biometals2001, 14, 191―204

doi: 10.1023/A:1012942511574
Aoki, S.; Kimura, E., Rev. Mol. Biotechnol. 2002, 90, 129―155

doi: 10.1016/S1389-0352(01)00070-8
Aoki, S.; Shiro, M.; Koike, T.; Kimura, E., J. Am. Chem. Soc. 2000, 122, 576―584

doi: 10.1021/ja993352i
Aoki, S.; Iwaida, K.; Hanamoto, N.; Shiro, M.; Kimura, E., J. Am. Chem. Soc. 2002, 124, 5256―5257

doi: 10.1021/ja020029y
Aoki, S.; Jikiba, A.; Takeda, K.; Kimura, E., J. Phys. Org. Chem. 2004, 17, 489―497

doi: 10.1002/poc.773
Aoki, S.; Zulkefeli, M.; Shiro, M.; Kohsako, M.; Takeda, K.; Kimura, E., J. Am. Chem. Soc. 2005, 127, 9129―9139

doi: 10.1021/ja050876b
Kimura, E.; Shiota, T.; Koike, T.; Shiro, M.; Kodama, M., J. Am. Chem. Soc. 1990, 112, 5805―5811

doi: 10.1021/ja00171a020
Koike, T.; Kimura, E., J. Am. Chem. Soc. 1991, 113, 8935―8941

doi: 10.1021/ja00023a048
Zhang, X.; van Eldik, R.; Koike, T.; Kimura, E., Inorg. Chem. 1993, 32, 5749―5755

doi: 10.1021/ic00077a017
Aoki, S.; Kimura, E., J. Am. Chem. Soc. 2000, 122, 4542―4548

doi: 10.1021/ja994537s
Kimura, E., Acc. Chem. Res. 2001, 34, 171―179

doi: 10.1021/ar000001w
Aoki, S.; Kimura, E., Chem. Rev. 2004, 104, 769―787

doi: 10.1021/cr020617u
Terech, P.; Weiss, R. G., Chem. Rev. 1997, 97, 3133―3160

doi: 10.1021/cr9700282
Lehn, J. M., Chem. Soc. Rev. 2007, 36, 151―160

doi: 10.1039/b616752g
van der Laan, S.; Feringa, B. L.; Kellogg, R. M.; van Esch, J., Langmuir2002, 18, 7136―7140

doi: 10.1021/la025561d
Deindörfer, P.; Geiger, T.; Schollmeyer, D.; Ye, J. H.; Zentel, R., J. Mater.Chem. 2006, 16, 351―358
Estroff, L. A.; Hamilton, A. D., Chem. Rev. 2004, 104, 1201―1218

doi: 10.1021/cr0302049
George, S. J.; Ajayaghosh, A., Chem. Eur. J2005, 11, 3217―3227

doi: 10.1002/chem.200401178
Yagai, S.; Kinoshita, T.; Higashi, M.; Kishikawa, K.; Nakanishi, T.; Karatsu, T.; Kitamura, A., J. Am. Chem. Soc. 2007, 129, 13277―13287

doi: 10.1021/ja075257c
Gupta, H.; Jain, S.; Mathur, R.; Mishra, P.; Mishra, A. K.; Velpandian, T., Drug Deliv. 2007, 14, 507―515

doi: 10.1080/10717540701606426
Miravet, J. F.; Escuder, B., Org. Lett. 2005, 7, 4791―4794

doi: 10.1021/ol0514045
Wu, J. C.; Yi, T.; Shu, T. M.; Yu, M. X.; Zhou, Z. G.; Xu, M.; Zhou, Y. F.; Zhang, H. J.; et al, Angew. Chem. Int.Ed. 2008, 47, 1063―1067

doi: 10.1002/anie.200703946
Shu, T.; Wu, J.; Lu, M.; Chen, L.; Yi, T.; Li, F.; Huang, C., J. Mater. Chem. 2008, 18, 886―893

doi: 10.1039/b715462c
Paulusse, J. M. J.; Sijbesma, R. P., Angew. Chem. Int. Ed. 2006, 45, 2334―2337

doi: 10.1002/anie.200503191
Yang, Z.; Ho, P. L.; Liang, G.; Chow, K. H.; Wang, Q.; Cao, Y.; Guo, Z.; Xu, B., J. Am. Chem. Soc. 2007, 129, 266―267

doi: 10.1021/ja0675604
Wang, C.; Zhang, D. Q.; Zhu, D. B., J. Am. Chem. Soc. 2005, 127, 16373―16374
Ajayaghosh, A.; Praveen, V. K., Acc. Chem. Res. 2007, 40, 644―656

doi: 10.1021/ar7000364
George, M.; Weiss, R. G., Acc. Chem. Res. 2006, 39, 489―497

doi: 10.1021/ar0500923
Boerakker, M. J.; Botterhuis, N. E.; Bomans, P. H. H.; Frederik, P. M.; Meijer, E. M.; Nolte, R. J. M.; Sommerdijk, N. A. J. M., Chem. Eur. J2006, 12, 6071―6080

doi: 10.1002/chem.200600089
Suzuki, T.; Shinkai, S.; Sada, K., Adv. Mater. 2006, 18, 1043―1046

doi: 10.1002/adma.200502552
Shklyarevskiy, I. O.; Jonkheijm, P.; Christianen, P. C. M.; Schenning, A. P. H. J.; Meijer, E. W.; Henze, O.; Kilbinger, A. F. M.; Feast, W. J.; et al, J. Am. Chem. Soc. 2005, 127, 1112―1113

doi: 10.1021/ja0431096
Weng, W.; Beck, J. B.; Jamieson, A. M.; Rowan, S. J., J. Am. Chem. Soc. 2006, 128, 11663―11672

doi: 10.1021/ja063408q
Fages, F., Angew. Chem. Int. Ed. 2006, 45, 1680―1682
Ajayaghosh, A.; Chithra, P.; Varghese, R., Angew. Chem. Int. Ed. 2007, 46, 230―233

doi: 10.1002/anie.200603611
Filby, M. H.; Steed, J. W., Coord. Chem. Rev. 2006, 250, 3200―3218

doi: 10.1016/j.ccr.2006.06.004
Applegarth, L.; Clark, N.; Richardson, A. C.; Parker, A. D. M.; Radosavljevic-Evans, I.; Goeta, A. E.; Howard, J. A. K.; Steed, J. W., Chem. Commun. 2005, 5423―5425
Tam, A. Y.; Wong, K. M.; Wang, G.; Yam, V. W., Chem. Commun.2007, 2028―2030

doi: 10.1039/b705062c
Hui, J. K. H.; Yu, Z.; MacLachlan, M. J., Angew.Chem. Int. Ed. 2007, 46, 7980―7983

doi: 10.1002/anie.200702680
Xing, B.; Choi, M. F.; Xu, B., Chem. Commun.2002, 362―363
Xing, B.; Choi, M. F.; Zhou, Z.; Xu, B., Langmuir2002, 18, 9654―9658

doi: 10.1021/la0256580
Tu, T.; Assenmacher, W.; Peterlik, H.; Weisbarth, R.; Nieger, M.; Dötz, K. H., Angew. Chem. Int. Ed. 2007, 46, 6368―6371

doi: 10.1002/anie.200701486
Zhou, Y.; Xu, M.; Yi, T.; Xiao, S.; Zhou, Z.; Li, F.; Huang, C., Langmuir2007, 23, 202―208

doi: 10.1021/la061530x
Koumura, N.; Kudo, M.; Tamaoki, N., Langmuir2004, 20, 9897―9900

doi: 10.1021/la048334f
de Loos, M.; van Esch, J.; Kellogg, R. M.; Feringa, B. L., Angew. Chem. Int. Ed. 2001, 40, 613―616

doi: 10.1002/1521-3773(20010202)40:3<613::AID-ANIE613>3.0.CO;2-K
Kumar, G. S.; Neckers, D. C., Chem. Rev. 1989, 89, 1915―1925
Kato, T., Science2002, 295, 2414―2418

doi: 10.1126/science.1070967
Mizoshita, N.; Hanabusa, K.; Kato, T., Adv. Funct. Mater. 2003, 13, 313―317

doi: 10.1002/adfm.200304275
Kitamura, T.; Nakaso, S.; Mizoshita, N.; Tochigi, Y.; Shimomura, T.; Moriyama, M.; Ito, K.; Kato, T., J. Am.Chem. Soc. 2005, 127, 14769―14775

doi: 10.1021/ja053496z
Mizoshita, N.; Suzuki, Y.; Hanabusa, K.; Kato, T., Adv. Mater. 2005, 17, 692―696

doi: 10.1002/adma.200401401
Zhao, Y.; Tong, X., Adv. Mater. 2003, 15, 1431―1435

doi: 10.1002/adma.200305120
Singh, A.; Tsao, L. I.; Markowitz, M.; Gaber, B. P., Langmuir1992, 8, 1570―1577

doi: 10.1021/la00042a013
Subat, M.; Borovik, A. S.; König, B., J. Am. Chem. Soc. 2004, 126, 3185―3190

doi: 10.1021/ja038980l
Jung, J. H.; Kobayashi, H.; Masuda, M.; Shimizu, T.; Shinkai, S., J. Am. Chem. Soc. 2001, 123, 8785―8789

doi: 10.1021/ja010508h
Estroff, L. A.; Leiserowitz, L.; Addadi, L.; Weiner, S.; Hamilton, A. D., Adv. Mater. 2003, 15, 38―42

doi: 10.1002/adma.200390004
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