3-Boryl-2,2′-bithiophene as a Versatile Core Skeleton for Full-Color Highly Emissive Organic Solids†
Atsushi Wakamiya Dr.
Department of Chemistry, Graduate School of Science, Nagoya University, and SORST, Japan Science and Technology Agency, Chikusa, Nagoya 464-8602, Japan, Fax: (+81) 52-789-5947
Search for more papers by this authorKenji Mori
Department of Chemistry, Graduate School of Science, Nagoya University, and SORST, Japan Science and Technology Agency, Chikusa, Nagoya 464-8602, Japan, Fax: (+81) 52-789-5947
Search for more papers by this authorShigehiro Yamaguchi Prof. Dr.
Department of Chemistry, Graduate School of Science, Nagoya University, and SORST, Japan Science and Technology Agency, Chikusa, Nagoya 464-8602, Japan, Fax: (+81) 52-789-5947
Search for more papers by this authorAtsushi Wakamiya Dr.
Department of Chemistry, Graduate School of Science, Nagoya University, and SORST, Japan Science and Technology Agency, Chikusa, Nagoya 464-8602, Japan, Fax: (+81) 52-789-5947
Search for more papers by this authorKenji Mori
Department of Chemistry, Graduate School of Science, Nagoya University, and SORST, Japan Science and Technology Agency, Chikusa, Nagoya 464-8602, Japan, Fax: (+81) 52-789-5947
Search for more papers by this authorShigehiro Yamaguchi Prof. Dr.
Department of Chemistry, Graduate School of Science, Nagoya University, and SORST, Japan Science and Technology Agency, Chikusa, Nagoya 464-8602, Japan, Fax: (+81) 52-789-5947
Search for more papers by this authorThis work was partially supported by SORST, JST, and the TOYOTA Motor Co.
Graphical Abstract
Farbenfroh: Durch Einstellen der Elektronendonoreigenschaften des π-konjugierten Bithiophen-Gerüsts wurden intensiv emittierende Festkörper erhalten, deren Maxima einen großen Teil des sichtbaren Spektrums abdecken (siehe Bild). Eine tiefrote Fluoreszenz mit großer Stokes-Verschiebung um 200 nm resultiert aus einem intramolekularen Charge-Transfer(CT)-Übergang vom verdrillten Bithiophen auf das Borzentrum.
Supporting Information
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References
- 1Examples of highly emissive organic solids:
- 1aC.-T. Chen, C.-L. Chiang, Y.-C. Lin, L.-H. Chan, C.-H. Huang, Z.-W. Tsai, C.-T. Chen, Org. Lett. 2003, 5, 1261;
- 1bH. Langhals, O. Krotz, K. Polborn, P. Mayer, Angew. Chem. 2005, 117, 2479;
10.1002/ange.200461610 Google ScholarAngew. Chem. Int. Ed. 2005, 44, 2427;
- 1cS. H. Lee, B.-B. Jang, Z. H. Kafafi, J. Am. Chem. Soc. 2005, 127, 9071;
- 1dY. Kim, J. Bouffard, S. E. Kooi, T. M. Swager, J. Am. Chem. Soc. 2005, 127, 13726;
- 1eZ. Xie, B. Yang, F. Li, G. Cheng, L. Liu, G. Yang, H. Xu, L. Ye, M. Hanif, S. Liu, D. Ma, Y. Ma, J. Am. Chem. Soc. 2005, 127, 14152;
- 1fA. Hayer, V. Halleux, A. Köhler, A. El-Garoughy, E. W. Meijer, J. Barberá, J. Tant, J. Levin, M. Lehmann, J. Gierschner, J. Cornil, Y. H. Geerts, J. Phys. Chem. B 2006, 110, 7653.
- 2C.-H. Zhao, A. Wakamiya, Y. Inukai, S. Yamaguchi, J. Am. Chem. Soc. 2006, 128, 15934.
- 3Reviews on organoboron materials:
- 3aC. D. Entwistle, T. B. Marder, Angew. Chem. 2002, 114, 3051;
10.1002/1521-3757(20020816)114:16<3051::AID-ANGE3051>3.0.CO;2-R Google ScholarAngew. Chem. Int. Ed. 2002, 41, 2927;10.1002/1521-3773(20020816)41:16<2927::AID-ANIE2927>3.0.CO;2-L CAS PubMed Web of Science® Google Scholar
- 3bC. D. Entwistle, T. B. Marder, Chem. Mater. 2004, 16, 4574.
- 4aP. J. Grisdale, J. L. R. Williams, M. E. Glogowski, B. E. Babb, J. Org. Chem. 1971, 36, 544;
- 4bJ. C. Doty, B. Babb, P. J. Grisdale, M. Glogowski, J. L. R. Williams, J. Organomet. Chem. 1972, 38, 229.
- 5aZ. Yuan, N. J. Taylor, T. B. Marder, I. D. Williams, S. K. Kurtz, L.-T. Cheng, J. Chem. Soc. Chem. Commun. 1990, 1489;
- 5bZ. Yuan, N. J. Taylor, Y. Sun, T. B. Marder, I. D. Williams, L.-T. Cheng, J. Organomet. Chem. 1993, 449, 27;
- 5cZ. Yuan, N. J. Taylor, R. Ramachandran, T. B. Marder, Appl. Organomet. Chem. 1996, 10, 305;
- 5dZ. Yuan, J. C. Collings, N. J. Taylor, T. B. Marder, C. Jardin, J.-F. Halet, J. Solid State Chem. 2000, 154, 5;
- 5eT. B. Marder et al., Chem. Eur. J. 2006, 12, 2758, see the Supporting Information.
- 6aM. Lequan, R. M. Lequan, C. K. Ching, J. Mater. Chem. 1991, 1, 997;
- 6bC. Branger, M. Lequan, R. M. Lequan, M. Barzoukas, A. Fort, J. Mater. Chem. 1996, 6, 555;
- 6cC. Branger, M. Lequan, R. M. Lequan, M. Large, F. Kajzar, Chem. Phys. Lett. 1997, 272, 265.
- 7aT. Noda, Y. Shirota, J. Am. Chem. Soc. 1998, 120, 9714;
- 7bT. Noda, H. Ogawa, Y. Shirota, Adv. Mater. 1999, 11, 283;
- 7cY. Shirota, M. Kinoshita, T. Noda, K. Okumoto, T. Ohara, J. Am. Chem. Soc. 2000, 122, 11021;
- 7dH. Doi, M. Kinoshita, K. Okumoto, Y. Shirota, Chem. Mater. 2003, 15, 1080.
- 8aS. Yamaguchi, T. Shirasaka, K. Tamao, Org. Lett. 2000, 2, 4129;
- 8bS. Yamaguchi, S. Akiyama, K. Tamao, J. Am. Chem. Soc. 2001, 123, 11372;
- 8cS. Yamaguchi, T. Shirasaka, S. Akiyama, K. Tamao, J. Am. Chem. Soc. 2002, 124, 8816;
- 8dY. Kubo, M. Yamamoto, M. Ikeda, M. Takeuchi, S. Shinkai, S. Yamaguchi, K. Tamao, Angew. Chem. 2003, 115, 2082;
10.1002/ange.200250788 Google ScholarAngew. Chem. Int. Ed. 2003, 42, 2036.
- 9aZ.-Q. Liu, Q. Fang, D. Wang, G. Xue, W.-T. Yu, Z.-S. Shao M.-H. Jiang, Chem. Commun. 2002, 2900;
- 9bZ.-Q. Liu, Q. Fang, D.-X. Cao, D. Wang, G.-B. Xu, Org. Lett. 2004, 6, 2933.
- 10aW.-L. Jia, D. Song, S. Wang, J. Org. Chem. 2003, 68, 701;
- 10bW.-L. Jia, D.-R. Bai, T. McCormick, Q.-D. Liu, M. Motala, R.-Y. Wang, C. Seward, Y. Tao, S. Wang, Chem. Eur. J. 2004, 10, 994;
- 10cW. L. Jia, M. J. Moran, Y. Y. Yuan, Z. H. Lu, S. Wang, J. Mater. Chem. 2005, 15, 3326;
- 10dW.-L. Jia, X. D. Feng, D. R. Bai, Z. H. Lu, S. Wang, G. Vamvounis, Chem. Mater. 2005, 17, 164;
- 10eQ.-D. Liu, M. S. Mudadu, R. Thummel, Y. Tao, S. Wang, Adv. Funct. Mater. 2005, 15, 143;
- 10fX. Y. Liu, D. R. Bai, S. Wang, Angew. Chem. 2006, 118, 5601; Angew. Chem. Int. Ed. 2006, 45, 5475.
- 11aA. Sundararaman, M. Victor, R. Varughese, F. Jäkle, J. Am. Chem. Soc. 2005, 127, 13748;
- 11bK. Parab, K. Venkatasubbaiah, F. Jäkle, J. Am. Chem. Soc. 2006, 128, 12879;
- 11cY. Qin, I. Kiburu, S. Shah, F. Jäkle, Org. Lett. 2006, 8, 5227.
- 12R. Stahl, C. Lambert, C. Kaiser, R. Wortmann, R. Jakober, Chem. Eur. J. 2006, 12, 2358.
- 13
- 13aT. E. Barder, S. D. Walker, J. R. Martinelli, S. L. Buchwald, J. Am. Chem. Soc. 2005, 127, 4685;
- 13bV. Farina, B. Krishnan, J. Am. Chem. Soc. 1991, 113, 9585.
- 14Crystal data for 1 and 8: see the Supporting Information. CCDC-629218 (1) and CCDC-629219 (8) 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.
- 15A similar small solvent dependence was also observed for π-extended 6 and 7, thus indicating that this is a general characteristic for the present π systems: see the Supporting Information.
- 16
- 16aK. R. Justin Thomas, J. T. Lin, M. Velusamy, Y.-T. Tao, C.-H. Chuen, Adv. Funct. Mater. 2004, 14, 83;
- 16bK. R. Justin Thomas, J. T. Lin, Y.-T. Tao, C.-H. Chuen, Adv. Mater. 2002, 14, 822;
- 16cS. Kato, T. Matsumoto, T. Ishi-i, T. Thiemann, M. Shigeiwa, H. Gorohmaru, S. Maeda, Y. Yamashita, S. Mataka, Chem. Commun. 2004, 2342;
- 16dS. Kato, T. Matsumoto, M. Shigeiwa, H. Goroumaru, S. Maeda, T. Ishi-i, S. Mataka, Chem. Eur. J. 2006, 12, 2303;
- 16eQ. Fang, B. Xu, B. Jiang, H. Fu, X. Chen, A. Cao, Chem. Commun. 2005, 1468;
- 16fJ. Jacob, S. Sax, T. Piok, E. J. W. List, A. C. Grimsdale, K. Müllen, J. Am. Chem. Soc. 2004, 126, 6987;
- 16gJ. Qu, C. Kohl, M. Pottek, K. Müllen, Angew. Chem. 2004, 116, 1554; Angew. Chem. Int. Ed. 2004, 43, 1528;
- 16hG. Barbarella, L. Favaretto, G. Sotgiu, M. Zambianchi, A. Bongini, C. Arbizzani, M. Mastragostino, M. Anni, G. Gigli, R. Cingolani, J. Am. Chem. Soc. 2000, 122, 11971;
- 16iS. Beaupré, M. Leclerc, Adv. Funct. Mater. 2002, 12, 192;
- 16jW.-C. Wu, H.-C. Yeh, L.-H. Chan, C.-T. Chen, Adv. Mater. 2002, 14, 1072.
- 17aQ. Hou, Y. Xu, W. Yang, M. Yuan, J. Peng, Y. Cao, J. Mater. Chem. 2002, 12, 2887;
- 17bR. Yang, R. Tian, J. Yan, Y. Zhang, J. Yang, Q. Hou, W. Yang, C. Zhang, Y. Cao, Macromolecules 2005, 38, 244;
- 17cJ. Yang, C. Jiang, Y. Zhang, R. Yang, W. Yang, Q. Hou, Y. Cao, Macromolecules 2004, 37, 1211;
- 17dQ. Peng, Z.-Y. Lu, Y. Huang, M.-G. Xie, S.-H. Han, J.-B. Peng, Y. Cao, Macromolecules 2004, 37, 260;
- 17eX. H. Zhang, B. J. Chen, X. Q. Lin, O. Y. Wong, C. S. Lee, H. L. Kwong, S. T. Lee, S. K. Wu, Chem. Mater. 2001, 13, 1565;
- 17fL.-H. Chan, Y.-D. Lee, C.-T. Chen, Macromolecules 2006, 39, 3262.
- 18
- 18aD. W. Brousmiche, J. M. Serin, J. M. J. Fréchet, G. S. He, T.-C. Lin, S. J. Chung, P. N. Prasad, J. Am. Chem. Soc. 2003, 125, 1448;
- 18bC. Hippius, F. Schlosser, M. O. Vysotsky, V. Böhmer, F. Würthner, J. Am. Chem. Soc. 2006, 128, 3870.
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