Artigo Revisado por pares

Visual Chiral Recognition through Enantioselective Metallogel Collapsing: Synthesis, Characterization, and Application of Platinum–Steroid Low‐Molecular‐Mass Gelators

2011; Wiley; Volume: 123; Issue: 29 Linguagem: Inglês

10.1002/ange.201180620

ISSN

1521-3757

Autores

Tao Tu, Weiwei Fang, Xiaoling Bao, Xinbao Li, Karl Heinz Dötz,

Tópico(s)

Polyoxometalates: Synthesis and Applications

Resumo

Angewandte ChemieVolume 123, Issue 29 p. 6731-6735 Zuschrift Visual Chiral Recognition through Enantioselective Metallogel Collapsing: Synthesis, Characterization, and Application of Platinum–Steroid Low-Molecular-Mass Gelators† Dr. Tao Tu, Corresponding Author Dr. Tao Tu [email protected] Shanghai Key Laboratory of Molecular Catalysts and Innovative Materials, Department of Chemistry, Fudan University, 220 Handan Road, 200433, Shanghai (China), Fax: (+86) 21-65102412Shanghai Key Laboratory of Molecular Catalysts and Innovative Materials, Department of Chemistry, Fudan University, 220 Handan Road, 200433, Shanghai (China), Fax: (+86) 21-65102412Search for more papers by this authorWeiwei Fang, Weiwei Fang Shanghai Key Laboratory of Molecular Catalysts and Innovative Materials, Department of Chemistry, Fudan University, 220 Handan Road, 200433, Shanghai (China), Fax: (+86) 21-65102412Search for more papers by this authorXiaoling Bao, Xiaoling Bao Shanghai Key Laboratory of Molecular Catalysts and Innovative Materials, Department of Chemistry, Fudan University, 220 Handan Road, 200433, Shanghai (China), Fax: (+86) 21-65102412Search for more papers by this authorXinbao Li, Xinbao Li Shanghai Key Laboratory of Molecular Catalysts and Innovative Materials, Department of Chemistry, Fudan University, 220 Handan Road, 200433, Shanghai (China), Fax: (+86) 21-65102412Search for more papers by this authorProf. Karl Heinz Dötz, Prof. Karl Heinz Dötz Kekulé-Institute of Organic Chemistry and Biochemistry, University of Bonn (Germany)Search for more papers by this author Dr. Tao Tu, Corresponding Author Dr. Tao Tu [email protected] Shanghai Key Laboratory of Molecular Catalysts and Innovative Materials, Department of Chemistry, Fudan University, 220 Handan Road, 200433, Shanghai (China), Fax: (+86) 21-65102412Shanghai Key Laboratory of Molecular Catalysts and Innovative Materials, Department of Chemistry, Fudan University, 220 Handan Road, 200433, Shanghai (China), Fax: (+86) 21-65102412Search for more papers by this authorWeiwei Fang, Weiwei Fang Shanghai Key Laboratory of Molecular Catalysts and Innovative Materials, Department of Chemistry, Fudan University, 220 Handan Road, 200433, Shanghai (China), Fax: (+86) 21-65102412Search for more papers by this authorXiaoling Bao, Xiaoling Bao Shanghai Key Laboratory of Molecular Catalysts and Innovative Materials, Department of Chemistry, Fudan University, 220 Handan Road, 200433, Shanghai (China), Fax: (+86) 21-65102412Search for more papers by this authorXinbao Li, Xinbao Li Shanghai Key Laboratory of Molecular Catalysts and Innovative Materials, Department of Chemistry, Fudan University, 220 Handan Road, 200433, Shanghai (China), Fax: (+86) 21-65102412Search for more papers by this authorProf. Karl Heinz Dötz, Prof. Karl Heinz Dötz Kekulé-Institute of Organic Chemistry and Biochemistry, University of Bonn (Germany)Search for more papers by this author First published: 06 July 2011 https://doi.org/10.1002/ange.201180620Citations: 61 † Financial support from the National Natural Science Foundation of China (No. 20902011), the Shanghai Municipal Science and Technology Commission (Qimingxing Program No. 10A1400500), the Shanghai Leading Academic Discipline Project (B108), and Shanghai Key Laboratory of Molecular Catalysts and Innovative Materials (2010MCIMKF04), Department of Chemistry, Fudan University is gratefully acknowledged. We thank Prof. Tao Yi and Prof. Qi-Lin Zhou for technical support. Read the full textAboutPDF ToolsRequest permissionAdd to favorites 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 Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat Graphical Abstract Sehen um zu glauben: Die optische chirale Erkennung von (R)- und (S)-Binap gelang mithilfe des enantioselektiven Kollabierens von Metallogelen, die mit neuartigen Gelatoren aus Platin und Pinzettenliganden mit aromatischem, Linker- und Steroidteil hergestellt wurden. Van-der-Waals-Wechselwirkungen, π-Stapelung und Metall-Metall-Bindung führen zur Aggregation und chiralen Erkennung. 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 ange_201180620_sm_miscellaneous_information.pdf11.6 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. References 1 1a Chiral Recognition in the Gas Phase (Ed.: ), Woodhead, Cambridge, UK, 2010; Google Scholar 1b Chirality in Drug Research (Eds.: ), Wiley-VCH, Weinheim, 2006; Google Scholar 1c Chirality in Natural and Applied Science (Eds.: ), Blackwell, Oxford, UK, 2002. Google Scholar 2 2aSelected recent reviews of chiral recognition: G. A. Hembury, V. V. Borovkov, Y. Inoue, Chem. Rev. 2008, 108, 1; 10.1021/cr050005k CASPubMedWeb of Science®Google Scholar 2bL. Pu, Chem. Rev. 2004, 104, 1687; 10.1021/cr030052h CASPubMedWeb of Science®Google Scholar 2cM. W. Peczuh, A. D. Hamilton, Chem. Rev. 2000, 100, 2479; 10.1021/cr9900026 CASPubMedWeb of Science®Google Scholar 2dF. Vögtle, P. Knops, Angew. Chem. 1991, 103, 972; 10.1002/ange.19911030810 Google ScholarAngew. Chem. Int. Ed. Engl. 1991, 30, 958. 10.1002/anie.199109581 Web of Science®Google Scholar 3 3aH.-L. Liu, Q. Peng, Y.-D. Wu, D. Chen, X.-L. Hou, M. Sabat, L. Pu, Angew. Chem. 2010, 122, 612; 10.1002/ange.200904889 Web of Science®Google ScholarAngew. Chem. Int. Ed. 2010, 49, 602; 10.1002/anie.200904889 CASPubMedWeb of Science®Google Scholar 3bL. Chi, J. Zhao, T. D. James, J. Org. Chem. 2008, 73, 4684; 10.1021/jo8007622 CASPubMedWeb of Science®Google Scholar 3cZ.-B. Li, J. Lin, M. Sabat, M. Hyacinth, L. Pu, J. Org. Chem. 2007, 72, 4905; 10.1021/jo0704715 CASPubMedWeb of Science®Google Scholar 3dJ. Heo, C. A. Mirkin, Angew. Chem. 2006, 118, 955; 10.1002/ange.200503343 Google ScholarAngew. Chem. Int. Ed. 2006, 45, 941. 10.1002/anie.200503343 CASPubMedWeb of Science®Google Scholar 4 4aS. J. Wezenberg, E. C. Escudero-Adán, J. Benet-Buchholz, A. W. Kleij, Org. Lett. 2008, 10, 3311; 10.1021/ol801167r CASPubMedWeb of Science®Google Scholar 4bB. García-Acosta, R. Martínez-Máñez, J. V. Ros-Lis, F. Sancenón, J. Soto, Tetrahedron Lett. 2008, 49, 1997; 10.1016/j.tetlet.2008.01.076 CASWeb of Science®Google Scholar 4cW. Kaminsky, E. Haussühl, L. D. Bastin, J. A. Subramony, B. Kahr, J. Cryst. Growth 2002, 234, 523; 10.1016/S0022-0248(01)01591-3 CASWeb of Science®Google Scholar 4dK. Tsubaki, M. Nuruzzaman, T. Kusumoto, N. Hayashi, B.-G. Wang, K. Fuji, Org. Lett. 2001, 3, 4071; 10.1021/ol016825a CASPubMedWeb of Science®Google Scholar 4eY. Kubo, S. Maeda, S. Tokita, M. Kubo, Nature 1996, 382, 522; 10.1038/382522a0 CASWeb of Science®Google Scholar 4fT. Nishi, A. Ikeda, T. Matsuda, S. Shinkai, J. Chem. Soc. Chem. Commun. 1991, 339; 10.1039/c39910000339 CASWeb of Science®Google Scholar 4gT. Kaneda, K. Hirose, S. Misumi, J. Am. Chem. Soc. 1989, 111, 742. 10.1021/ja00184a058 CASWeb of Science®Google Scholar 5H.-L. Liu, X.-L. Hou, L. Pu, Angew. Chem. 2009, 121, 388; 10.1002/ange.200804538 Web of Science®Google ScholarAngew. Chem. Int. Ed. 2009, 48, 382. 10.1002/anie.200804538 CASPubMedWeb of Science®Google Scholar 6Selected recent reviews: Google Scholar 6a Molecular Gels: Materials with Self-Assembled Fibrillar Networks (Eds.: ), Springer, Dordrecht, 2006; Google Scholar 6bM. George, R. G. Weiss, Acc. Chem. Res. 2006, 39, 489; 10.1021/ar0500923 CASPubMedWeb of Science®Google Scholar 6c"Low Molecular Mass Gelator", Top. Curr. Chem. 2005, 256, 1; Google Scholar 6dN. M. Sangeetha, U. Maitra, Chem. Soc. Rev. 2005, 34, 821; 10.1039/b417081b CASPubMedWeb of Science®Google Scholar 6eF. J. M. Hoeben, P. Jonkheijm, E. W. Meijer, A. P. H. J. Schenning, Chem. Rev. 2005, 105, 1491; 10.1021/cr030070z CASPubMedWeb of Science®Google Scholar 6fL. A. Estroff, A. D. Hamilton, Chem. Rev. 2004, 104, 1201; 10.1021/cr0302049 CASPubMedWeb of Science®Google Scholar 6gJ. H. van Esch, B. L. Feringa, Angew. Chem. 2000, 112, 2351; 10.1002/1521-3757(20000703)112:13 3.0.CO;2-2 Google ScholarAngew. Chem. Int. Ed. 2000, 39, 2263. 10.1002/1521-3773(20000703)39:13 3.0.CO;2-V CASPubMedWeb of Science®Google Scholar 7 7aX. Yu, Q. Liu, J. Wu, M. Zhang, X. Cao, S. Zhang, Q. Wang, L. Chen, T. Yi, Chem. Eur. J. 2010, 16, 9099; 10.1002/chem.201000187 CASPubMedWeb of Science®Google Scholar 7bJ. Wu, T. Yi, T. Shu, M. Yu, Z. Zhou, M. Xu, Y. Zhou, H. Zhang, J. Han, F. Li, C. Huang, Angew. Chem. 2008, 120, 1079; 10.1002/ange.200703946 Google ScholarAngew. Chem. Int. Ed. 2008, 47, 1063. 10.1002/anie.200703946 CASPubMedWeb of Science®Google Scholar 8 8aX. Chen, Z. Huang, S.-Y. Chen, K. Li, X.-Q. Yu, L. Pu, J. Am. Chem. Soc. 2010, 132, 7297; 10.1021/ja102480t CASPubMedWeb of Science®Google Scholar 8bM. de Loos, J. van Esch, R. M. Kellogg, B. L. Feringa, Angew. Chem. 2001, 113, 633; 10.1002/1521-3757(20010202)113:3 3.0.CO;2-R Google ScholarAngew. Chem. Int. Ed. 2001, 40, 613. 10.1002/1521-3773(20010202)40:3 3.0.CO;2-K CASPubMedWeb of Science®Google Scholar 9F. Fages, Angew. Chem. 2006, 118, 1710; 10.1002/ange.200503704 Google ScholarAngew. Chem. Int. Ed. 2006, 45, 1680. 10.1002/anie.200503704 CASPubMedWeb of Science®Google Scholar 10J. Liu, P. He, J. Yan, X. Fang, J. Peng, K. Liu, Y. Fang, Adv. Mater. 2008, 20, 2508. 10.1002/adma.200703195 CASWeb of Science®Google Scholar 11 11aA. Gansäuer, I. Winkler, T. Klawonn, R. J. M. Nolte, M. C. Feiters, H. G. Börner, J. Hentschel, K. H. Dötz, Organometallics 2009, 28, 1377; 10.1021/om801022c CASWeb of Science®Google Scholar 11bT. Klawonn, A. Gansäuer, I. Winkler, T. Lauterbach, D. Franke, R. J. M. Nolte, M. C. Feiters, H. Börner, J. Hentschel, K. H. Dötz, Chem. Commun. 2007, 1894. 10.1039/B701565H CASPubMedWeb of Science®Google Scholar 12 12aT. Tu, X. Bao, W. Assenmacher, H. Peterlik, J. Daniels, K. H. Dötz, Chem. Eur. J. 2009, 15, 1853; 10.1002/chem.200802116 CASPubMedWeb of Science®Google Scholar 12bT. Tu, W. Assenmacher, H. Peterlik, G. Schnakenburg, K. H. Dötz, Angew. Chem. 2008, 120, 7236; 10.1002/ange.200801628 Google ScholarAngew. Chem. Int. Ed. 2008, 47, 7127; 10.1002/anie.200801628 CASPubMedWeb of Science®Google Scholar 12cT. Tu, W. Assenmacher, H. Peterlik, R. Weisbarth, M. Nieger, K. H. Dötz, Angew. Chem. 2007, 119, 6486; 10.1002/ange.200701486 Google ScholarAngew. Chem. Int. Ed. 2007, 46, 6368. 10.1002/anie.200701486 CASPubMedWeb of Science®Google Scholar 13 13aT. Tu, X. Feng, Z. Wang, X. Liu, Dalton Trans. 2010, 39, 10598; 10.1039/c0dt01083a CASPubMedWeb of Science®Google Scholar 13bT. Tu, H. Mao, C. Herbert, M. Xu, K. H. Dötz, Chem. Commun. 2010, 46, 7796; 10.1039/c0cc03107k CASPubMedWeb of Science®Google Scholar 13cT. Tu, J. Malineni, X. Bao, K. H. Dötz, Adv. Synth. Catal. 2009, 351, 1029; 10.1002/adsc.200800768 CASWeb of Science®Google Scholar 13dT. Tu, J. Malineni, K. H. Dötz, Adv. Synth. Catal. 2008, 350, 1791. 10.1002/adsc.200800244 CASWeb of Science®Google Scholar 14A. Takahashi, M. Sakai, T. Kato, Polym. J. 1980, 12, 335. 10.1295/polymj.12.335 CASWeb of Science®Google Scholar 15 15aP. Terech, F. Volino, R. Ramasseul, J. Phys. 1985, 46, 895; 10.1051/jphys:01985004606089500 CASWeb of Science®Google Scholar 15b Small-Angle X-ray Scattering (Eds.: ), Academic Press, London, 1982. Google Scholar 16Selected examples: Google Scholar 16aJ. J. Yan, A. L.-F. Chow, C.-H. Leung, R. W.-Y. Sun, D.-L. Ma, C.-M. Che, Chem. Commun. 2010, 46, 3893; 10.1039/c001216e CASPubMedWeb of Science®Google Scholar 16bY. Chen, K. Li, W. Lu, S. S.-Y. Chui, C.-W. Ma, C.-M. Che, Angew. Chem. 2009, 121, 10093; 10.1002/ange.200905678 Google ScholarAngew. Chem. Int. Ed. 2009, 48, 9909; 10.1002/anie.200905678 CASPubMedWeb of Science®Google Scholar 16cW. Lu, S. S.-Y. Chui, K.-M. Ng, C.-M. Che, Angew. Chem. 2008, 120, 4644; 10.1002/ange.200704450 Google ScholarAngew. Chem. Int. Ed. 2008, 47, 4568; 10.1002/anie.200704450 CASPubMedWeb of Science®Google Scholar 16dW. Lu, N. Zhu, C.-M. Che, Chem. Commun. 2002, 900. 10.1039/b200723a CASPubMedWeb of Science®Google Scholar 17 17aJ.-H. Xie, Q.-L. Zhou, Acc. Chem. Res. 2008, 41, 581; 10.1021/ar700137z CASPubMedWeb of Science®Google Scholar 17bY.-M. Li, F.-Y. Kwong, W.-Y. Yu, A. S. C. Chan, Coord. Chem. Rev. 2007, 251, 2119. 10.1016/j.ccr.2007.07.020 CASWeb of Science®Google Scholar 18 18aJ. Y. Lee, O. K. Farha, J. Roberts, K. A. Scheidt, S. B. T. Nguyen, J. T. Hupp, Chem. Soc. Rev. 2009, 38, 1450; 10.1039/b807080f CASPubMedWeb of Science®Google Scholar 18bL. Ma, C. Abney, W. Lin, Chem. Soc. Rev. 2009, 38, 1248. 10.1039/b807083k CASPubMedWeb of Science®Google Scholar Citing Literature Volume123, Issue29July 11, 2011Pages 6731-6735 This is the German version of Angewandte Chemie. Note for articles published since 1962: Do not cite this version alone. Take me to the International Edition version with citable page numbers, DOI, and citation export. We apologize for the inconvenience. ReferencesRelatedInformation

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