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Temperature‐Controlled Supramolecular Vesicles Modulated by p ‐Sulfonatocalix[5]arene with Pyrene

2010; Wiley; Volume: 16; Issue: 27 Linguagem: Inglês

10.1002/chem.201000991

ISSN

1521-3765

Autores

Kui Wang, Dong‐Sheng Guo, Yu Liu,

Tópico(s)

Luminescence and Fluorescent Materials

Resumo

Chemistry – A European JournalVolume 16, Issue 27 p. 8006-8011 Communication Temperature-Controlled Supramolecular Vesicles Modulated by p-Sulfonatocalix[5]arene with Pyrene Kui Wang, Kui Wang Department of Chemistry, State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071 (P.R. China), Fax: (+86) 22-23503625Search for more papers by this authorDong-Sheng Guo Dr., Dong-Sheng Guo Dr. Department of Chemistry, State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071 (P.R. China), Fax: (+86) 22-23503625Search for more papers by this authorYu Liu Prof. Dr., Yu Liu Prof. Dr. [email protected] Department of Chemistry, State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071 (P.R. China), Fax: (+86) 22-23503625Search for more papers by this author Kui Wang, Kui Wang Department of Chemistry, State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071 (P.R. China), Fax: (+86) 22-23503625Search for more papers by this authorDong-Sheng Guo Dr., Dong-Sheng Guo Dr. Department of Chemistry, State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071 (P.R. China), Fax: (+86) 22-23503625Search for more papers by this authorYu Liu Prof. Dr., Yu Liu Prof. Dr. [email protected] Department of Chemistry, State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071 (P.R. China), Fax: (+86) 22-23503625Search for more papers by this author First published: 12 July 2010 https://doi.org/10.1002/chem.201000991Citations: 82Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Graphical Abstract Supramolecular vesicles were successfully constructed on the basis of host–guest complex formation between p-sulfonatocalix[5]arene and 1-pyrenemethylaminium. The obtained vesicles exhibit benign water solubility, self-labeled fluorescence, and more importantly, temperature-response characteristics; these features mean that the vesicles can act as potential delivery models for special substrates (see figure; DOX=doxorubicin hydrochloride). References 1 1aS. Zhou, C. Burger, B. Chu, M. Sawamura, N. Nagahama, M. Toganoh, U. E. Hackler, H. Isobe, E. Nakamura, Science 2001, 291, 1944– 1947; 1bA. Mueller, D. F. O'Brien, Chem. Rev. 2002, 102, 727– 757; 1cD. E. Discher, A. Eisenberg, Science 2002, 297, 967– 973; 1dD. M. Vriezema, M. C. Aragonès, J. A. A. W. Elemans, J. J. L. M. Cornelissen, A. E. Rowan, R. J. M. Nolte, Chem. Rev. 2005, 105, 1445– 1489; 1eT. Kunitake, Angew. Chem. 1992, 104, 692– 710; Angew. Chem. Int. Ed. Engl. 1992, 31, 709– 726; 1fS. Kolusheva, T. Shahal, R. Jelinek, J. Am. Chem. Soc. 2000, 122, 776– 780; 1gT. Renkes, H. J. Schäfer, P. M. Siemens, E. Neumann, Angew. Chem. 2000, 112, 2566– 2570; Angew. Chem. Int. Ed. 2000, 39, 2512– 2516; 1hB. J. Ravoo, R. Darcy, Angew. Chem. 2000, 112, 4494– 4496; Angew. Chem. Int. Ed. 2000, 39, 4324– 4326; 1iM. Brettreich, S. Burghardt, C. Böttcher, T. Bayerl, S. Bayerl, A. Hirsch, Angew. Chem. 2000, 112, 1915– 1918; Angew. Chem. Int. Ed. 2000, 39, 1845– 1848; 1jA. M. Cassell, C. L. Asplund, J. M. Tour, Angew. Chem. 1999, 111, 2565– 2568; Angew. Chem. Int. Ed. 1999, 38, 2403– 2405; 1kT. Dwars, E. Paetzold, G. Oehme, Angew. Chem. 2005, 117, 7338– 7364; Angew. Chem. Int. Ed. 2005, 44, 7174– 7199. 2Y. Wang, H. Xu, X. Zhang, Adv. Mater. 2009, 21, 2849– 2864. 3 3aN. Kimizuka, T. Kawasaki, T. Kunitake, J. Am. Chem. Soc. 1993, 115, 4387– 4388; 3bN. Kimizuka, T. Kawasaki, K. Hirata, T. Kunitake, J. Am. Chem. Soc. 1998, 120, 4094– 4104. 4 4aW. Pisula, M. Kastler, D. Wasserfallen, J. W. F. Robertson, F. Nolde, C. Kohl, K. Müllen. Angew. Chem. 2006, 118, 834–838; Angew. Chem. Int. Ed. 2006, 45, 819– 823; Angew. Chem. Int. Ed. 2006, 45, 819– 823; 4bC. Wang, S. Yin, S. Chen, H. Xu, Z. Wang, X. Zhang, Angew. Chem. 2008, 120, 9189– 9192; Angew. Chem. Int. Ed. 2008, 47, 9049– 9052; 4cA. Okabe, T. Fukushima, K. Ariga, T. Aida, Angew. Chem. 2002, 114, 3564– 3567; Angew. Chem. Int. Ed. 2002, 41, 3414– 3417. 5 5aF. Würthner, Chem. Commun. 2004, 1564– 1579; 5bX. Zhang, Z. Chen, F. Würthner, J. Am. Chem. Soc. 2007, 129, 4886– 4887; 5cX. Zhang, S. Rehm, M. M. Safont-Sempere, F. Würthner, Nat. Chem. 2009, 1, 623– 629. 6 6aY. Wang, N. Ma, Z. Wang, X. Zhang, Angew. Chem. 2007, 119, 2881– 2884; Angew. Chem. Int. Ed. 2007, 46, 2823– 2826; 6bP. Wan, Y. Jiang, Y. Wang, Z. Wang, X. Zhang, Chem. Commun. 2008, 5710– 5712; 6cY. H. Ko, E. Kim, I. Hwang, K. Kim, Chem. Commun. 2007, 1305– 1315; 6dK. Kim, W. S. Jeon, J.-K. Kang, J. K. Lee, S. Y. Jon, T. Kim, K. Kim, Angew. Chem. 2003, 115, 2395– 2398; Angew. Chem. Int. Ed. 2003, 42, 2293– 2296; 6eC. Park, I. H. Lee, S. Lee, Y. Song, M. Rhue, C. Kim, Proc. Natl. Acad. Sci. USA 2006, 103, 1199– 1203. 7D.-S. Guo, K. Chen, H.-Q. Zhang, Y. Liu, Chem. Asian J. 2009, 4, 436– 445. 8 8aF. Perret, A. N. Lazar, A. W. Coleman, Chem. Commun. 2006, 2425– 2438; 8bA. W. Coleman, S. Jebors, S. Cecillon, P. Perret, D. Garin, D. Marti-Battle, M. Moulin, New J. Chem. 2008, 32, 780– 782; 8cK. Wang, D.-S. Guo, H.-Q. Zhang, D. Li, X.-L. Zheng, Y. Liu, J. Med. Chem. 2009, 52, 6402– 6412; 8dV. D. Uzunova, C. Cullinane, K. Brix, W. M. Nau, A. I. Day, Org. Biomol. Chem. 2010, 8, 2037– 2042; 8eV. J. Stella, R. A. Rajewski, Pharm. Res. 1997, 14, 556– 567; 8fK. Uekama, F. Hirayama, T. Irie, Chem. Rev. 1998, 98, 2045– 2076. 9 9aY. J. Jeon, P. K. Bharadwaj, S. W. Choi, J. W. Lee, K. Kim, Angew. Chem. 2002, 114, 4654– 4656; Angew. Chem. Int. Ed. 2002, 41, 4474– 4476; 9bB. Jing, X. Chen, X. Wang, C. Yang, Y. Xie, H. Qiu, Chem. Eur. J. 2007, 13, 9137– 9142; 9cJ. Zeng, K. Shi, Y. Zhang, X. Sun, B. Zhang, Chem. Commun. 2008, 3753– 3755. 10A. Ikeda, S. Shinkai, Chem. Rev. 1997, 97, 1713– 1734. 11J. N. Israelachvilli, Intermolecular and Surface Forces, Academic Press, New York, 1985. 12M. Kellermann, W. Bauer, A. Hirsch, B. Schade, K. Ludwig, C. Böttcher, Angew. Chem. 2004, 116, 3019– 3022; Angew. Chem. Int. Ed. 2004, 43, 2959– 2962. 13M. Lee, S.-J. Lee, L.-H. Jiang, J. Am. Chem. Soc. 2004, 126, 12724– 12725. 14aE.-H. Ryu, Y. Zhao, Org. Lett. 2004, 6, 3187– 3189; 14bK. Sugiyama, K. Esumi, Y. Koide, Langmuir 1996, 12, 6006– 6010. 15 15aY. Tanaka, M. Miyachi, Y. Kokube, Angew. Chem. 1999, 111, 565– 567; Angew. Chem. Int. Ed. 1999, 38, 504– 506; 15bS. Houmadi, D. Coquière, L. Legrand, M. C. Fauré, M. Goldmann, O. Reinaud, S. Rémita, Langmuir 2007, 23, 4849– 4855; 15cN. Micali, V. Villari, G. M. L. Consoli, F. Cunsolo, C. Geraci, Phys. Rev. E 2006, 73, 051904– 051908. 16N. Basilio, L. García-Río, Chem. Eur. J. 2009, 15, 9315– 9319. 17C. Bize, J.-C. Garrigues, M. Blanzat, I. Rico-Lattes, O. Bistri, B. Colasson, O. Reinaud, Chem. Commun. 2010, 46, 586– 588. 18K. Kalyanasundaram, J. K. Thomas, J. Am. Chem. Soc. 1977, 99, 2039– 2044. 19M. Rehm, M. Frank, J. Schatz, Tetrahedron Lett. 2009, 50, 93– 96. 20L. D. C. Baldi, E. T. Iamazaki, T. D. Z. Atvars, Dyes Pigm. 2008, 76, 669– 676. 21Y. Liu, D.-S. Guo, H.-Y. Zhang, F. Ding, K. Chen, H.-B. Song, Chem. Eur. J. 2007, 13, 466– 472. 22 22aX. Guo, F. C. Szoka, Acc. Chem. Res. 2003, 36, 335– 341; 22bF. Chécot, S. Lecommandoux, Y. Gnanou, H.-A. Klok, Angew. Chem. 2002, 114, 1395– 1399; Angew. Chem. Int. Ed. 2002, 41, 1339– 1343; 22cY. Sumida, A. Masuyama, M. Takasu, T. Kida, Y. Nakatsuji, I. Ikeda, M. Nojima, Langmuir 2001, 17, 609– 612; 22dM. Johnsson, A. Wagenaar, J. B. F. N. Engberts, J. Am. Chem. Soc. 2003, 125, 757– 760; 22eJ. Zhu, R. J. Munn, M. H. Nantz, J. Am. Chem. Soc. 2000, 122, 2645– 2646; 22fD. C. Drummond, M. Zignani, J.-C. Leroux, Prog. Lipid Res. 2000, 39, 409– 460. 23M. Nakayama, T. Okano, T. Miyazaki, F. Kohori, K. Sakai, M. Yokoyama, J. Controlled Release 2006, 115, 46– 56. 24 24aD.-S. Guo, K. Wang, Y. Liu, J. Inclusion Phenom. Macrocyclic Chem. 2008, 62, 1– 21; 24bZ. Chen, A. Lohr, C. R. Saha-Möller, F. Würthner, Chem. Soc. Rev. 2009, 38, 564– 584; 24cZ. Chen, V. Stepanenko, V. Dehm, P. Prins, L. D. A. Siebbeles, J. Seibt, P. Marquetand, V. Engel, F. Würthner, Chem. Eur. J. 2007, 13, 436– 449. 25C. Giacomelli, V. Schmidt, R. Borsali, Macromolecules 2007, 40, 2148– 2157. 26 26aH. Yin, Z. Zhou, J. Huang, R. Zheng, Y. Zhang, Angew. Chem. 2003, 115, 2238– 2241; Angew. Chem. Int. Ed. 2003, 42, 2188– 2191; 26bH. Yin, Y. Lin, J. Huang, J. Ye, Langmuir 2007, 23, 4225– 4230; 26cH. Yin, J. Huang, Y. Lin, Y. Zhang, S. Qiu, J. Ye, J. Phys. Chem. B 2005, 109, 4104– 4110; 26dR. T. Buwalda, M. C. A. Stuart, J. B. F. N. Engberts, Langmuir 2000, 16, 6780– 6786; 26eS. V. G. Menon, C. Manohar, F. Lequeux, Chem. Phys. Lett. 1996, 263, 727– 732; 26fD. Otten, L. Löbbecke, K. Beyer, Biophys. J. 1995, 68, 584– 597; 26gP. R. Majhi, A. Blump, J. Phys. Chem. B 2002, 106, 10753– 10763; 26hK. Bryskhe, S. Bulut, U. Olsson, J. Phys. Chem. B 2005, 109, 9265– 9274; 26iP. A. Hassan, B. S. Valaulikar, C. Manohar, F. Kern, L. Bourdieu, S. J. Candau, Langmuir 1996, 12, 4350– 4357; 26jK. Tsuchiya, H. Nakanishi, H. Sakai, M. Abe, Langmuir 2004, 20, 2117– 2122; 26kH. Yin, J. Huang, Y. Gao, H. Fu, Langmuir 2005, 21, 2656– 2659; 26lB. F. B. Silva, E. F. Marques, U. Olsson, Langmuir 2008, 24, 10746– 10754. 27J. W. Steed, C. P. Johnson, C. L. Barnes, R. K. Juneja, J. L. Atwood, S. Reilly, R. L. Hollis, P. H. Smith, D. L. Clark, J. Am. Chem. Soc. 1995, 117, 11426– 11433. Citing Literature Supporting Information Detailed facts of importance to specialist readers are published as "Supporting Information". Such documents are peer-reviewed, but not copy-edited or typeset. They are made available as submitted by the authors. Filename Description chem_201000991_sm_miscellaneous_information.pdf1.2 MB miscellaneous_information Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article. Volume16, Issue27July 19, 2010Pages 8006-8011 ReferencesRelatedInformation

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