Artigo Acesso aberto Revisado por pares

Light‐Triggered Guest Uptake and Release by a Photochromic Coordination Cage

2012; Wiley; Volume: 52; Issue: 4 Linguagem: Inglês

10.1002/anie.201207373

ISSN

1521-3773

Autores

Muxin Han, Reent Michel, Bice He, Yu‐Sheng Chen, Dietmar Stalke, Michael John, Guido H. Clever,

Tópico(s)

Molecular Sensors and Ion Detection

Resumo

Angewandte Chemie International EditionVolume 52, Issue 4 p. 1319-1323 Communication Light-Triggered Guest Uptake and Release by a Photochromic Coordination Cage† Muxin Han, Muxin Han Institute for Inorganic Chemistry, Georg-August University Göttingen, Tammannstrasse 4, 37077 Göttingen (Germany) http://www.clever-lab.deSearch for more papers by this authorReent Michel, Reent Michel Institute for Inorganic Chemistry, Georg-August University Göttingen, Tammannstrasse 4, 37077 Göttingen (Germany) http://www.clever-lab.deSearch for more papers by this authorDr. Bice He, Dr. Bice He Institute for Inorganic Chemistry, Georg-August University Göttingen, Tammannstrasse 4, 37077 Göttingen (Germany) http://www.clever-lab.deSearch for more papers by this authorDr. Yu-Sheng Chen, Dr. Yu-Sheng Chen Center for Advanced Radiation Source (ChemMatCARS), The University of Chicago c/o APS/ANL (USA)Search for more papers by this authorProf. Dr. Dietmar Stalke, Prof. Dr. Dietmar Stalke Institute for Inorganic Chemistry, Georg-August University Göttingen, Tammannstrasse 4, 37077 Göttingen (Germany) http://www.clever-lab.deSearch for more papers by this authorDr. Michael John, Dr. Michael John Institute for Inorganic Chemistry, Georg-August University Göttingen, Tammannstrasse 4, 37077 Göttingen (Germany) http://www.clever-lab.deSearch for more papers by this authorProf. Dr. Guido H. Clever, Corresponding Author Prof. Dr. Guido H. Clever [email protected] Institute for Inorganic Chemistry, Georg-August University Göttingen, Tammannstrasse 4, 37077 Göttingen (Germany) http://www.clever-lab.deInstitute for Inorganic Chemistry, Georg-August University Göttingen, Tammannstrasse 4, 37077 Göttingen (Germany) http://www.clever-lab.deSearch for more papers by this author Muxin Han, Muxin Han Institute for Inorganic Chemistry, Georg-August University Göttingen, Tammannstrasse 4, 37077 Göttingen (Germany) http://www.clever-lab.deSearch for more papers by this authorReent Michel, Reent Michel Institute for Inorganic Chemistry, Georg-August University Göttingen, Tammannstrasse 4, 37077 Göttingen (Germany) http://www.clever-lab.deSearch for more papers by this authorDr. Bice He, Dr. Bice He Institute for Inorganic Chemistry, Georg-August University Göttingen, Tammannstrasse 4, 37077 Göttingen (Germany) http://www.clever-lab.deSearch for more papers by this authorDr. Yu-Sheng Chen, Dr. Yu-Sheng Chen Center for Advanced Radiation Source (ChemMatCARS), The University of Chicago c/o APS/ANL (USA)Search for more papers by this authorProf. Dr. Dietmar Stalke, Prof. Dr. Dietmar Stalke Institute for Inorganic Chemistry, Georg-August University Göttingen, Tammannstrasse 4, 37077 Göttingen (Germany) http://www.clever-lab.deSearch for more papers by this authorDr. Michael John, Dr. Michael John Institute for Inorganic Chemistry, Georg-August University Göttingen, Tammannstrasse 4, 37077 Göttingen (Germany) http://www.clever-lab.deSearch for more papers by this authorProf. Dr. Guido H. Clever, Corresponding Author Prof. Dr. Guido H. Clever [email protected] Institute for Inorganic Chemistry, Georg-August University Göttingen, Tammannstrasse 4, 37077 Göttingen (Germany) http://www.clever-lab.deInstitute for Inorganic Chemistry, Georg-August University Göttingen, Tammannstrasse 4, 37077 Göttingen (Germany) http://www.clever-lab.deSearch for more papers by this author First published: 03 December 2012 https://doi.org/10.1002/anie.201207373Citations: 434 † M.H. thanks the CaSuS program of Lower Saxony for a PhD fellowship. We thank the Fonds der Chemischen Industrie for financial support, R. Machinek and Prof. Dr. C. Griesinger for NMR measurements, and Dr. H. Frauendorf for ESI measurements. ChemMatCARS Sector 15 is principally supported by the National Science Foundation/Department of Energy under grant No. NSF/CHE-0822838. Use of the Advanced Photon Source was supported by the U.S. Department of Energy, Office of Science, Office of Basic Energy Sciences, Contract No. DE-AC02-06CH11357. Read 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 Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat Graphical Abstract A guiding light is sufficient to switch back and forth between the flexible and the stretched, rigid form of a self-assembled coordination cage based on two square-planar-coordinated PdII ions and four ligands with a photochromic dithienylethene (DTE) backbone. The light-driven interconversion is clean and reversible and allows to control the encapsulation and release of the guest [B12F12]2−. 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 anie_201207373_sm_miscellaneous_information.pdf2.8 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 1aA. Rajbanshi, B. A. Moyer, R. Custelcean, Cryst. Growth Des. 2011, 11, 2702; 1bW. Meng, B. Breiner, K. Rissanen, J. D. Thoburn, J. K. Clegg, J. R. Nitschke, Angew. Chem. 2011, 123, 3541; Angew. Chem. Int. Ed. 2011, 50, 3479. 2 2aP. Mal, B. Breiner, K. Rissanen, J. R. Nitschke, Science 2009, 324, 1697; 2bI. A. Riddell, M. M. J. Smulders, J. K. Clegg, J. R. Nitschke, Chem. Commun. 2011, 47, 457. 3 3aD. Cram, M. Tanner, R. Thomas, Angew. Chem. 1991, 103, 1048; Angew. Chem. Int. Ed. Engl. 1991, 30, 1024; 3bK. Goto, R. Okazaki, Liebigs Ann./Recueil 1997, 2393; 3cM. Ziegler, J. Brumaghim, K. Raymond, Angew. Chem. 2000, 112, 4285; Angew. Chem. Int. Ed. 2000, 39, 4119; 3dD. Fiedler, R. G. Bergman, K. N. Raymond, Angew. Chem. 2006, 118, 759; Angew. Chem. Int. Ed. 2006, 45, 745; 3eM. Kawano, Y. Kobayashi, T. Ozeki, M. Fujita, J. Am. Chem. Soc. 2006, 128, 6558; 3fF. Hapiot, S. Tilloy, E. Monflier, Chem. Rev. 2006, 106, 767; 3gT. Iwasawa, R. J. Hooley, J. Rebek, Science 2007, 317, 493; 3hR. J. Hooley, J. Rebek, Chem. Biol. 2009, 16, 255; 3iC.-Y. Gao, L. Zhao, M.-X. Wang, J. Am. Chem. Soc. 2012, 134, 824. 4 4aJ. L. Sessler, P. Gale, W.-S. Cho, S. J. Rowan, Anion Receptor Chemistry (Monographs in Supramolecular Chemistry), Royal Society of Chemistry, London, 2006; 4bR. Custelcean, J. Bosano, P. V. Bonnesen, V. Kertesz, B. P. Hay, Angew. Chem. 2009, 121, 4085; Angew. Chem. Int. Ed. 2009, 48, 4025; 4cS. O. Kang, J. M. Llinares, V. W. Day, K. Bowman-James, Chem. Soc. Rev. 2010, 39, 3980; 4dM. Wang, V. Vajpayee, S. Shanmugaraju, Y.-R. Zheng, Z. Zhao, H. Kim, P. S. Mukherjee, K.-W. Chi, P. J. Stang, Inorg. Chem. 2011, 50, 1506; 4eJ. A. Thomas, Dalton Trans. 2011, 40, 12005. 5 5aT. D. Nguyen, Y. Liu, S. Saha, K. C. F. Leung, J. F. Stoddart, J. I. Zink, J. Am. Chem. Soc. 2007, 129, 626; 5bP. Mal, D. Schultz, K. Beyeh, K. Rissanen, J. R. Nitschke, Angew. Chem. 2008, 120, 8421; Angew. Chem. Int. Ed. 2008, 47, 8297; 5cF. Schmitt, J. Freudenreich, N. P. E. Barry, L. Juillerat-Jeanneret, G. Süss-Fink, B. Therrien, J. Am. Chem. Soc. 2012, 134, 754; 5dZ. Ma, B. Moulton, Coord. Chem. Rev. 2011, 255, 1623; 5eJ. E. M. Lewis, E. L. Gavey, S. A. Cameron, J. D. Crowley, Chem. Sci. 2012, 3, 778. 6 6aD. Vriezema, M. Aragones, J. Elemans, J. Cornelissen, A. Rowan, R. Nolte, Chem. Rev. 2005, 105, 1445; 6bM. Yoshizawa, J. K. Klosterman, M. Fujita, Angew. Chem. 2009, 121, 3470; Angew. Chem. Int. Ed. 2009, 48, 3418; 6c Molecular Encapsulation: Organic Reactions in Constrained Systems (Eds.: ), Wiley, Hoboken, 2010; 6dM. J. Wiester, P. A. Ulmann, C. A. Mirkin, Angew. Chem. 2011, 123, 118; Angew. Chem. Int. Ed. 2011, 50, 114. 7For one way out of this dilemma, see: 7aD. Fiedler, H. van Halbeek, R. G. Bergman, K. N. Raymond, J. Am. Chem. Soc. 2006, 128, 10240; 7bC. J. Hastings, M. D. Pluth, R. G. Bergman, K. N. Raymond, J. Am. Chem. Soc. 2010, 132, 6938. 8For other approaches towards light-triggered catalysis, see: 8aD. Sud, T. B. Norsten, N. R. Branda, Angew. Chem. 2005, 117, 2055; Angew. Chem. Int. Ed. 2005, 44, 2019; 8bR. S. Stoll, S. Hecht, Angew. Chem. 2010, 122, 5176; Angew. Chem. Int. Ed. 2010, 49, 5054; 8cJ. Wang, B. L. Feringa, Science 2011, 331, 1429; 8dU. Lüning, Angew. Chem. 2012, 124, 8285; Angew. Chem. Int. Ed. 2012, 51, 8163. 9G. H. Clever, S. Tashiro, M. Shionoya, J. Am. Chem. Soc. 2010, 132, 9973. 10 10aH. Dube, D. Ajami, J. Rebek, Angew. Chem. 2010, 122, 3260; Angew. Chem. Int. Ed. 2010, 49, 3192; 10bH. Dube, J. Rebek, Angew. Chem. 2012, 124, 3261; Angew. Chem. Int. Ed. 2012, 51, 3207. 11The blocking of voltage-gated ion channels by light-switchable binders is comparable to encapsulation processes in artificial cages: M. R. Banghart, A. Mourot, D. L. Fortin, J. Z. Yao, R. H. Kramer, D. Trauner, Angew. Chem. 2009, 121, 9261; Angew. Chem. Int. Ed. 2009, 48, 9097. 12G. H. Clever in Molecules at Work (Ed.: ), Wiley-VCH, Weinheim, 2012. 13M. Irie, M. Kato, J. Am. Chem. Soc. 1985, 107, 1024. 14S. Shinkai, M. Ishihara, K. Ueda, O. Manabe, J. Incl. Phenom. 1984, 2, 111. 15M. Blank, L. Soo, N. Wassermann, B. Erlanger, Science 1981, 214, 70. 16R. Rojanathanes, T. Tuntulani, W. Bhanthumnavin, M. Sukwattanasinitt, Org. Lett. 2005, 7, 3401. 17A. Ueno, H. Yoshimura, R. Saka, T. Osa, J. Am. Chem. Soc. 1979, 101, 2779. 18 18aR. Reuter, N. Hostettler, M. Neuburger, H. Wegner, Eur. J. Org. Chem. 2009, 5647; 18bN. Iwasawa, H. Takahagi, K. Ono, K. Fujii, H. Uekusa, Chem. Commun. 2012, 48, 7477; 18cS. Chen, L.-J. Chen, H.-B. Yang, H. Tian, W. Zhu, J. Am. Chem. Soc. 2012, 134, 13596. 19H. Kai, S. Nara, K. Kinbara, T. Aida, J. Am. Chem. Soc. 2008, 130, 6725. 20Covalently attached azobenzenes were used for switching the interior hydrophobicity (but not structure) of a coordination cage: T. Murase, S. Sato, M. Fujita, Angew. Chem. 2007, 119, 5225; Angew. Chem. Int. Ed. 2007, 46, 5133. 21 21aM. Fujita, K. Umemoto, M. Yoshizawa, N. Fujita, T. Kusukawa, K. Biradha, Chem. Commun. 2001, 509; 21bS. J. Dalgarno, N. P. Power, J. L. Atwood, Coord. Chem. Rev. 2008, 252, 825; 21cD. Tranchemontagne, Z. Ni, M. O’Keeffe, O. Yaghi, Angew. Chem. 2008, 120, 5214; Angew. Chem. Int. Ed. 2008, 47, 5136. 22Several other examples of coordination cages obeying the general formula [M2L4]4+ where M is a square-planar-coordinated metal ion, such as PdII or PtII, and L are bis(pyridyl) ligands bridging the two metal centers have been reported; see, for example: 22aD. A. McMorran, P. J. Steel, Angew. Chem. 1998, 110, 3495; Angew. Chem. Int. Ed. 1998, 37, 3295; 22bD. K. Chand, K. Biradha, M. Fujita, Chem. Commun. 2001, 1652; 22cC. Su, Y. P. Cai, C. Chen, M. D. Smith, W. Kaim, H. C. zur Loye, J. Am. Chem. Soc. 2003, 125, 8595; 22dN. L. S. Yue, D. J. Eisler, M. C. Jennings, R. J. Puddephatt, Inorg. Chem. 2004, 43, 7671; 22eG. H. Clever, S. Tashiro, M. Shionoya, Angew. Chem. 2009, 121, 7144; Angew. Chem. Int. Ed. 2009, 48, 7010; 22fP. Liao, B. W. Langloss, A. M. Johnson, E. R. Knudsen, F. S. Tham, R. R. Julian, R. J. Hooley, Chem. Commun. 2010, 46, 4932; 22gN. Kishi, Z. Li, K. Yoza, M. Akita, M. Yoshizawa, J. Am. Chem. Soc. 2011, 133, 11438; 22hG. H. Clever, W. Kawamura, S. Tashiro, M. Shiro, M. Shionoya, Angew. Chem. 2012, 124, 2660; Angew. Chem. Int. Ed. 2012, 51, 2606; 22iS. Freye, J. Hey, A. Torras Galán, D. Stalke, R. Herbst Irmer, M. John, G. H. Clever, Angew. Chem. 2012, 124, 2233; Angew. Chem. Int. Ed. 2012, 51, 2191; 22jD. M. Engelhard, S. Freye, K. Grohe, M. John, G. H. Clever, Angew. Chem. 2012, 124, 4828; Angew. Chem. Int. Ed. 2012, 51, 4747. 23M. Irie, Chem. Rev. 2000, 100, 1685. 24 24aS. Fraysse, C. Coudret, J. P. Launay, Eur. J. Inorg. Chem. 2000, 1581; 24bB. He, O. S. Wenger, J. Am. Chem. Soc. 2011, 133, 17027. 25Y. Ishibashi, M. Fujiwara, T. Umesato, H. Saito, S. Kobatake, M. Irie, H. Miyasaka, J. Phys. Chem. C 2011, 115, 4265. 26G. H. Clever, M. Shionoya, Chem. Eur. J. 2010, 16, 11792. 27 27aT. Weilandt, U. Kiehne, J. Bunzen, G. Schnakenburg, A. Lützen, Chem. Eur. J. 2010, 16, 2418; 27bN. Ousaka, J. K. Clegg, J. R. Nitschke, Angew. Chem. 2012, 124, 1493; Angew. Chem. Int. Ed. 2012, 51, 1464. 28M. Han, J. Hey, W. Kawamura, D. Stalke, M. Shionoya, G. H. Clever, Inorg. Chem. 2012, 51, 9574. 29G. H. Clever, W. Kawamura, M. Shionoya, Inorg. Chem. 2011, 50, 4689. 30P. Thordarson, Chem. Soc. Rev. 2011, 40, 1305. 31R. F. Barth, J. A. Coderre, M. Vicente, T. E. Blue, Clin. Cancer Res. 2005, 11, 3987. 32E. R. Kay, D. A. Leigh, F. Zerbetto, Angew. Chem. 2007, 119, 72; Angew. Chem. Int. Ed. 2007, 46, 72. Citing Literature Volume52, Issue4January 21, 2013Pages 1319-1323 ReferencesRelatedInformation

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