Thiatriphyrin(2.1.1): A Core‐Modified Contracted Porphyrin
2013; Wiley; Volume: 125; Issue: 12 Linguagem: Inglês
10.1002/ange.201209678
ISSN1521-3757
AutoresDaiki Kuzuhara, Yuka Sakakibara, Shigeki Mori, Tetsuo Okujima, Hidemitsu Uno, Hiroko Yamada,
Tópico(s)Magnetism in coordination complexes
ResumoAngewandte ChemieVolume 125, Issue 12 p. 3444-3447 Zuschrift Thiatriphyrin(2.1.1): A Core-Modified Contracted Porphyrin† Dr. Daiki Kuzuhara, Dr. Daiki Kuzuhara Graduate School of Materials Science, Nara Institute of Science and Technology, Ikoma 630-0192 (Japan)Search for more papers by this authorYuka Sakakibara, Yuka Sakakibara Graduate School of Materials Science, Nara Institute of Science and Technology, Ikoma 630-0192 (Japan)Search for more papers by this authorDr. Shigeki Mori, Dr. Shigeki Mori Department of Molecular Science, Integrated Center for Sciences, Ehime University, Matsuyama 790-8577 (Japan)Search for more papers by this authorProf. Dr. Tetsuo Okujima, Prof. Dr. Tetsuo Okujima Department of Chemistry and Biology, Graduate School of Science and Engineering, Ehime University, Matsuyama 790-8577 (Japan)Search for more papers by this authorProf. Dr. Hidemitsu Uno, Prof. Dr. Hidemitsu Uno Department of Chemistry and Biology, Graduate School of Science and Engineering, Ehime University, Matsuyama 790-8577 (Japan)Search for more papers by this authorProf. Dr. Hiroko Yamada, Corresponding Author Prof. Dr. Hiroko Yamada [email protected] Graduate School of Materials Science, Nara Institute of Science and Technology, Ikoma 630-0192 (Japan) CREST, JST, Chiyoda-ku, Tokyo 102-0075 (Japan)Graduate School of Materials Science, Nara Institute of Science and Technology, Ikoma 630-0192 (Japan)Search for more papers by this author Dr. Daiki Kuzuhara, Dr. Daiki Kuzuhara Graduate School of Materials Science, Nara Institute of Science and Technology, Ikoma 630-0192 (Japan)Search for more papers by this authorYuka Sakakibara, Yuka Sakakibara Graduate School of Materials Science, Nara Institute of Science and Technology, Ikoma 630-0192 (Japan)Search for more papers by this authorDr. Shigeki Mori, Dr. Shigeki Mori Department of Molecular Science, Integrated Center for Sciences, Ehime University, Matsuyama 790-8577 (Japan)Search for more papers by this authorProf. Dr. Tetsuo Okujima, Prof. Dr. Tetsuo Okujima Department of Chemistry and Biology, Graduate School of Science and Engineering, Ehime University, Matsuyama 790-8577 (Japan)Search for more papers by this authorProf. Dr. Hidemitsu Uno, Prof. Dr. Hidemitsu Uno Department of Chemistry and Biology, Graduate School of Science and Engineering, Ehime University, Matsuyama 790-8577 (Japan)Search for more papers by this authorProf. Dr. Hiroko Yamada, Corresponding Author Prof. Dr. Hiroko Yamada [email protected] Graduate School of Materials Science, Nara Institute of Science and Technology, Ikoma 630-0192 (Japan) CREST, JST, Chiyoda-ku, Tokyo 102-0075 (Japan)Graduate School of Materials Science, Nara Institute of Science and Technology, Ikoma 630-0192 (Japan)Search for more papers by this author First published: 11 February 2013 https://doi.org/10.1002/ange.201209678Citations: 18 † We thank S. Katao for the measurements of X-ray diffraction and M. Yamamura and Y. Nishikawa for ESIMS measurements. This research was partly supported by Grants-in-Aid (No. 24655034 to H.Y. and D.K.) and the Green Photonics Project at NAIST sponsored by the Ministry of Education, Culture, Sports, Science and Technology, MEXT (Japan). 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 Das kontrahierte Porphyrin Thiatriphyrin(2.1.1) mit modifiziertem Kern, das als freie Base instabil ist, wurde durch McMurry-Kupplung mit p-Tolylsubstituenten ausgestattet und dann in verschiedene Alkoxy-substituierte Derivate umgewandelt (siehe Schema; DBU=1,8-Diazabicyclo[5.4.0]undec-7-en). Diese wurden in Gegenwart von Trifluoressigsäure in protonierte Thiatriphyrine(2.1.1) überführt, die moderate Aromatizität aufweisen. Supporting Information As a service to our authors and readers, this journal provides supporting information supplied by the authors. Such materials are peer reviewed and may be re-organized for online delivery, but are not copy-edited or typeset. Technical support issues arising from supporting information (other than missing files) should be addressed to the authors. Filename Description ange_201209678_sm_miscellaneous_information.pdf14.8 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. Meller, A. Ossko, Monatsh. Chem. 1972, 103, 150–155; 10.1007/BF00912939 CASWeb of Science®Google Scholar 1bC. G. Claessens, D. González-Rodríguez, T. Torres, Chem. Rev. 2002, 102, 835–853. 10.1021/cr0101454 CASPubMedWeb of Science®Google Scholar 2 2aY. Inokuma, J. H. Kwon, T. K. Ahn, M.-C. Yoo, D. Kim, A. Osuka, Angew. Chem. 2006, 118, 975–978; 10.1002/ange.200503426 Google ScholarAngew. Chem. Int. Ed. 2006, 45, 961–964; 10.1002/anie.200503426 CASPubMedWeb of Science®Google Scholar 2bY. Inokuma, Z. S. Yoon, D. Kim, A. Osuka, J. Am. Chem. Soc. 2007, 129, 4747–4761; 10.1021/ja069324z CASPubMedWeb of Science®Google Scholar 2cY. Inokuma, A. Osuka, Dalton Trans. 2008, 2517–2526; 10.1039/b719808f CASPubMedWeb of Science®Google Scholar 2dA. Osuka, E. Tsurumaki, T. Tanaka, Bull. Chem. Soc. Jpn. 2011, 84, 679–697. 10.1246/bcsj.20110118 CASWeb of Science®Google Scholar 3N. Kobayashi, Y. Takeuchi, A. Matsuda, Angew. Chem. 2007, 119, 772–774; 10.1002/ange.200603520 Google ScholarAngew. Chem. Int. Ed. 2007, 46, 758–760. 10.1002/anie.200603520 CASPubMedWeb of Science®Google Scholar 4 4aB. del Rey, U. Keller, T. Torres, G. Rojo, F. Agulló-López, S. Nonell, C. Martí, S. Brasselet, I. Ledoux, J. Zyss, J. Am. Chem. Soc. 1998, 120, 12808–12817; 10.1021/ja980508q CASWeb of Science®Google Scholar 4bE. Tsurumaki, Y. Inokuma, S. Easwaramoorthi, J. M. Lim, D. Kim, A. Osuka, Chem. Eur. J. 2009, 15, 237–247; 10.1002/chem.200801802 CASPubMedWeb of Science®Google Scholar 4cS. Easwaramoorthi, J.-Y. Shin, S. Cho, P. Kim, Y. Inokuma, E. Tsurumaki, A. Osuka, D. Kim, Chem. Eur. J. 2009, 15, 12005–12017. 10.1002/chem.200901671 CASPubMedWeb of Science®Google Scholar 5 5aY. Inokuma, S. Easwaramoorthi, S. Y. Jang, K. S. Kim, D. Kim, A. Osuka, Angew. Chem. 2008, 120, 4918–4921; 10.1002/ange.200801192 Google ScholarAngew. Chem. Int. Ed. 2008, 47, 4840–4843. 10.1002/anie.200801192 CASPubMedWeb of Science®Google Scholar 6 6aY.-H. Chen, J.-H. Chang, G.-R. Lee, I.-W. Wu, J.-H. Fang, C.-I. Wu, T.-W. Pi, Appl. Phys. Lett. 2009, 95, 133302; 10.1063/1.3237173 CASWeb of Science®Google Scholar 6bG. E. Morse, M. G. Helander, J. F. Maka, Z.-H. Lu, T. P. Bender, ACS Appl. Mater. Interfaces 2010, 2, 1934–1944. 10.1021/am1002603 CASWeb of Science®Google Scholar 7 7aK. L. Mutolo, E. I. Mayo, B. P. Rand, S. R. Forrest, M. E. Thompson, J. Am. Chem. Soc. 2006, 128, 8108–8109; 10.1021/ja061655o CASPubMedWeb of Science®Google Scholar 7bN. Beaumont, S. W. Cho, P. Sullivan, D. Newby, K. E. Smith, T. S. Jones, Adv. Funct. Mater. 2012, 22, 561–566. 10.1002/adfm.201101782 CASWeb of Science®Google Scholar 8 8aZ.-L. Xue, Z. Shen, J. Mack, D. Kuzuhara, H. Yamada, T. Okujima, N. Ono, X.-Z. You, N. Kobayashi, J. Am. Chem. Soc. 2008, 130, 16478–16479; 10.1021/ja8068769 CASPubMedWeb of Science®Google Scholar 8bZ.-L. Xue, J. Mack, H. Lu, L. Zhang, X.-Z. You, D. Kuzuhara, M. Stillman, H. Yamada, S. Yamauchi, N. Kobayashi, Z. Shen, Chem. Eur. J. 2011, 17, 4396–4407. 10.1002/chem.201003100 CASPubMedWeb of Science®Google Scholar 9D. Kuzuhara, H. Yamada, Z.-L. Xue, T. Okujima, S. Mori, Z. Shen, H. Uno, Chem. Commun. 2011, 47, 722–724. 10.1039/C0CC04286B CASPubMedWeb of Science®Google Scholar 10K. S. Anju, S. Ramakrishnan, A. Srinivasan, Org. Lett. 2011, 13, 2498–2501. 10.1021/ol200668a CASPubMedWeb of Science®Google Scholar 11L. Latos-Grażyński in The Porphyrin Handbook, Vol. 2 (Eds.: ), Academic Press, San Diego, 2000, pp. 361–416. Google Scholar 12P. J. Chmielewski, L. Latos-Grażyński, Coord. Chem. Rev. 2005, 249, 2510–2533. 10.1016/j.ccr.2005.05.015 CASWeb of Science®Google Scholar 13 13aR. Myśliborski, L. Latos-Grażyński, L. Szterenberg, T. Lis, Angew. Chem. 2006, 118, 3752–3756; 10.1002/ange.200600589 Google ScholarAngew. Chem. Int. Ed. 2006, 45, 3670–3674; 10.1002/anie.200600589 CASPubMedWeb of Science®Google Scholar 13bK. S. Kim, J. M. Lim, R. Myśliborski, M. Pawlicki, L. Latos-Grażyński, D. Kim, J. Phys. Chem. Lett. 2011, 2, 477–481. 10.1021/jz1017366 CASWeb of Science®Google Scholar 14C. H. Lee, K. T. Oh, Tetrahedron Lett. 1999, 40, 1921–1924. 10.1016/S0040-4039(99)00044-1 CASWeb of Science®Google Scholar 15CCDC 912982 (8), 912983 (6 a), and 912984 (TTPH+) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif. Google Scholar 16Gaussian 09, M. Frisch, et al., Gaussian, Inc. Wallingford CT, 2009. Google Scholar 17K. A. Brameld, B. Kuhn, D. C. Reuter, M. Stahl, J. Chem. Inf. Model. 2008, 48, 1–24. 10.1021/ci7002494 CASPubMedWeb of Science®Google Scholar 18A. Młodzianowska, L. Latos-Grażyński, L. Szterenberg, M. Stépień, Inorg. Chem. 2007, 46, 6950–6957. 10.1021/ic700647v CASPubMedWeb of Science®Google Scholar 19 19aA. Berlicka, L. Latos-Grażyński, T. Lis, Angew. Chem. 2005, 117, 5422–5425; 10.1002/ange.200501635 Google ScholarAngew. Chem. Int. Ed. 2005, 44, 5288–5291; 10.1002/anie.200501635 CASPubMedWeb of Science®Google Scholar 19bE. Nojman, A. Berlicka, L. Szterenberg, L. Latos-Grażyński, Inorg. Chem. 2012, 51, 3247–3260. 10.1021/ic2027175 CASPubMedWeb of Science®Google Scholar 20H. J. Callot, E. Schaeffer, J. Org. Chem. 1977, 42, 1567–1570. 10.1021/jo00429a019 CASWeb of Science®Google Scholar 21P. R. Schleyer, C. Maerker, A. Dransfeld, H. Jiao, N. J. R. E. Hommes, J. Am. Chem. Soc. 1996, 118, 6317–6318. 10.1021/ja960582d CASPubMedWeb of Science®Google Scholar Citing Literature Volume125, Issue12March 18, 2013Pages 3444-3447 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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