Fusing Porphyrins and Phospholes: Synthesis and Analysis of a Phosphorus-Containing Porphyrin
Corresponding Author
Dr. Tomohiro Higashino
Department of Molecular Engineering, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto, 615-8510 Japan
Search for more papers by this authorTomoki Yamada
Department of Molecular Engineering, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto, 615-8510 Japan
Search for more papers by this authorDr. Tsuneaki Sakurai
Department of Molecular Engineering, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto, 615-8510 Japan
Search for more papers by this authorProf. Dr. Shu Seki
Department of Molecular Engineering, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto, 615-8510 Japan
Search for more papers by this authorCorresponding Author
Prof. Dr. Hiroshi Imahori
Department of Molecular Engineering, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto, 615-8510 Japan
Institute for Integrated Cell Material Sciences (WPI-iCeMS), Kyoto University, Nishikyo-ku, Kyoto, 615-8510 Japan
Search for more papers by this authorCorresponding Author
Dr. Tomohiro Higashino
Department of Molecular Engineering, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto, 615-8510 Japan
Search for more papers by this authorTomoki Yamada
Department of Molecular Engineering, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto, 615-8510 Japan
Search for more papers by this authorDr. Tsuneaki Sakurai
Department of Molecular Engineering, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto, 615-8510 Japan
Search for more papers by this authorProf. Dr. Shu Seki
Department of Molecular Engineering, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto, 615-8510 Japan
Search for more papers by this authorCorresponding Author
Prof. Dr. Hiroshi Imahori
Department of Molecular Engineering, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto, 615-8510 Japan
Institute for Integrated Cell Material Sciences (WPI-iCeMS), Kyoto University, Nishikyo-ku, Kyoto, 615-8510 Japan
Search for more papers by this authorGraphical Abstract
A phosphole-fused porphyrin dimer as a representative of a new class of phosphorus-containing porphyrins was synthesized. This structure exhibits remarkably broadened absorption as well as unique optoelectronic properties and is a good electron acceptor owing to the unique phosphole-fused structure.
Abstract
A phosphole-fused porphyrin dimer, as a representative of a new class of porphyrins with a phosphorus atom, was synthesized for the first time. The porphyrin dimer exhibits remarkably broadened absorption, indicating effective π-conjugation over the two porphyrins through the phosphole moiety. The porphyrin dimer possesses excellent electron-accepting character, which is comparable to that of a representative electron-accepting material, [60]PCBM. These results provide access to a new class of phosphorus-containing porphyrins with unique optoelectronic properties.
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References
- 1
- 1a The Porphyrin Handbook, Vol. 1–10 (Eds.: ), Academic Press, San Diego, 2000;
- 1bD. Gust, T. A. Moore, A. L. Moore, Acc. Chem. Res. 2001, 34, 40–48;
- 1cD. Holten, D. F. Bocian, J. S. Lindsey, Acc. Chem. Res. 2002, 35, 57–69;
- 1dH. Imahori, J. Phys. Chem. B 2004, 108, 6130–6143;
- 1eM. Ethirajan, Y. Chen, P. Joshi, R. K. Pandey, Chem. Soc. Rev. 2011, 40, 340–362;
- 1fT. Tanaka, A. Osuka, Chem. Soc. Rev. 2015, 44, 943–969;
- 1gT. Higashino, H. Imahori, Dalton Trans. 2015, 44, 448–463.
- 2
- 2aB. M. J. M. Suijkerbuijk, R. J. M. Klein Gebbink, Angew. Chem. Int. Ed. 2008, 47, 7396–7421; Angew. Chem. 2008, 120, 7506–7532;
- 2bM. O. Senge, Chem. Commun. 2011, 47, 1943–1960;
- 2cH. Yorimitsu, A. Osuka, Asian J. Org. Chem. 2013, 2, 356–373.
- 3
- 3aP. J. Chmielewski, L. Latos-Grażyński, Coord. Chem. Rev. 2005, 249, 2510–2533;
- 3bI. Gupta, M. Ravikanth, Coord. Chem. Rev. 2006, 250, 468–518.
- 4
- 4aH. Segawa, K. Kunimoto, K. Susumu, M. Taniguchi, T. Shimidzu, J. Am. Chem. Soc. 1994, 116, 11193–11194;
- 4bK. Susumu, K. Kunimoto, H. Segawa, T. Shimidzu, J. Phys. Chem. 1995, 99, 29–34.
- 5
- 5aA. Młodzianowska, L. Latos-Grażyński, L. Szterenberg, Inorg. Chem. 2008, 47, 6364–6374;
- 5bE. Pacholska-Dudziak, F. Ulatowski, Z. Ciunik, L. Latos-Grażyński, Chem. Eur. J. 2009, 15, 10924–10929.
- 6
- 6aY. Matano, K. Matsumoto, Y. Nakao, H. Uno, S. Sakaki, H. Imahori, J. Am. Chem. Soc. 2008, 130, 4588–4589;
- 6bY. Matano, K. Matsumoto, H. Hayashi, Y. Nakao, T. Kumpulainen, V. Chukharev, N. V. Tkachenko, H. Lemmetyinen, S. Shimizu, N. Kobayashi, D. Sakamaki, A. Ito, K. Tanaka, H. Imahori, J. Am. Chem. Soc. 2012, 134, 1825–1839;
- 6cK. Fujimoto, T. Yoneda, H. Yorimitsu, A. Osuka, Angew. Chem. Int. Ed. 2014, 53, 1127–1130; Angew. Chem. 2014, 126, 1145–1148.
- 7
- 7aY. Matano, H. Imahori, Acc. Chem. Res. 2009, 42, 1193–1204;
- 7bY. Matano, T. Nakabuchi, T. Miyajima, H. Imahori, H. Nakano, Org. Lett. 2006, 8, 5713–5716;
- 7cY. Matano, T. Nakabuchi, S. Fujishige, H. Nakano, H. Imahori, J. Am. Chem. Soc. 2008, 130, 16446–16447;
- 7dY. Matano, M. Nakashima, T. Nakabuchi, H. Imahori, S. Fujishige, H. Nakano, Org. Lett. 2008, 10, 553–556;
- 7eT. Nakabuchi, Y. Matano, H. Imahori, Org. Lett. 2010, 12, 1112–1115;
- 7fY. Matano, T. Nakabuchi, H. Imahori, Pure Appl. Chem. 2010, 82, 583–593;
- 7gT. Nakabuchi, M. Nakashima, S. Fujishige, H. Nakano, Y. Matano, H. Imahori, J. Org. Chem. 2010, 75, 375–389.
- 8
- 8aA. Fukazawa, S. Yamaguchi, Chem. Asian J. 2009, 4, 1386–1400;
- 8bY. Matano, H. Imahori, Org. Biomol. Chem. 2009, 7, 1258–1271;
- 8cY. Ren, T. Baumgartner, Dalton Trans. 2012, 41, 7792–7800;
- 8dT. Baumgartner, Acc. Chem. Res. 2014, 47, 1613–1622;
- 8eM. Stolar, T. Baumgartner, Chem. Asian J. 2014, 9, 1212–1225.
- 9T. Higashino, H. Imahori, Chem. Eur. J. 2015, 21, 13375–13381.
- 10Crystallographic data for 12: C74H53N8PS⋅C3H8O⋅0.5(C2H4Cl2), Mr=1226.84, monoclinic, C2/c (No.15), a=23.139(10), b=18.670(8), c=30.139(12) Å, β=90.068(11)°, V=13020(9) Å3, ρcalcd=1.252 g cm−3, Z=8, R1=0.0836 [I>2σ(I)], wR2=0.3069 (all data), GOF=1.067. CCDC 1495318 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre.
- 11
- 11aA. Wakamiya, H. Nishimura, T. Fukushima, F. Suzuki, A. Saeki, S. Seki, I. Osaka, T. Sasamori, M. Murata, Y. Murata, H. Kaji, Angew. Chem. Int. Ed. 2014, 53, 5800–5804; Angew. Chem. 2014, 126, 5910–5914;
- 11bW. Nakanishi, N. Matsuyama, D. Hara, A. Saeki, S. Hitosugi, S. Seki, H. Isobe, Chem. Asian J. 2014, 9, 1782–1785.
- 12C. Ryppa, M. O. Senge, S. S. Hatscher, E. Kleinpeter, P. Wacker, U. Schilde, A. Wiehe, Chem. Eur. J. 2005, 11, 3427–3442.
- 13
- 13a5,10,15,20-Tetra(4-tolyl)porphyrin (λQ=647 nm in CH2Cl2): S. Zakavi, S. Hoseini, RSC Adv. 2015, 5, 106774–106786;
- 13bβ-β′-bis[5,10,15,20-tetra(4-tolyl)porphyrin] (λQ=655 nm in CH2Cl2): G. Bringmann, D. C. G. Götz, T. A. M. Gulder, T. H. Gehrke, T. Bruhn, T. Kupfer, K. Radacki, H. Braunschweig, A. Heckmann, C. Lambert, J. Am. Chem. Soc. 2008, 130, 17812–17825.
- 14
- 14aY. Matano, T. Miyajima, T. Fukushima, H. Kaji, Y. Kimura, H. Imahori, Chem. Eur. J. 2008, 14, 8102–8115;
- 14bA. Saito, T. Miyajima, M. Nakashima, T. Fukushima, H. Kaji, Y. Matano, H. Imahori, Chem. Eur. J. 2009, 15, 10000–10004;
- 14cY. Matano, A. Saito, T. Fukushima, Y. Tokudome, F. Suzuki, D. Sakamaki, H. Kaji, A. Ito, K. Tanaka, H. Imahori, Angew. Chem. Int. Ed. 2011, 50, 8016–8020; Angew. Chem. 2011, 123, 8166–8170;
- 14dY. Dienes, M. Eggenstein, T. Kárpáti, T. C. Sutherland, L. Nyulászi, T. Baumgartner, Chem. Eur. J. 2008, 14, 9878–9889;
- 14eY. Ren, Y. Dienes, S. Hettel, M. Parvez, B. Hoge, T. Baumgartner, Organometallics 2009, 28, 734–740;
- 14fH. Tsuji, K. Sato, Y. Sato, E. Nakamura, J. Mater. Chem. 2009, 19, 3364–3366;
- 14gH. Tsuji, K. Sato, Y. Sato, E. Nakamura, Chem. Asian J. 2010, 5, 1294–1297;
- 14hP.-A. Bouit, A. Escande, R. Szűcs, D. Szieberth, C. Lescop, L. Nyulászi, M. Hissler, R. Réau, J. Am. Chem. Soc. 2012, 134, 6524–6527;
- 14iF. Riobé, R. Szűcs, P.-A. Bouit, D. Tondelier, B. Geffroy, F. Aparicio, J. Buendía, L. Sánchez, R. Réau, L. Nyulászi, M. Hissler, Chem. Eur. J. 2015, 21, 6547–6556.
- 15J. Pommerehne, H. Vestweber, W. Guss, R. F. Mahrt, H. Bässler, M. Porsch, J. Daub, Adv. Mater. 1995, 7, 551–554.
- 16
- 16aJ. C. Hummelen, B. W. Knight, F. LePeq, F. Wudl, J. Yao, C. L. Wilkins, J. Org. Chem. 1995, 60, 532–538;
- 16bR. Tao, T. Umeyama, T. Higashino, T. Koganezawa, H. Imahori, Chem. Commun. 2015, 51, 8233–8236.
- 17
- 17aY. Liu, J. Zhao, Z. Li, C. Mu, W. Ma, H. Hu, K. Jiang, H. Lin, H. Ade, H. Yan, Nat. Commun. 2014, 5, 5293;
- 17bJ. E. Anthony, A. Facchetti, M. Heeney, S. R. Marder, X. Zhan, Adv. Mater. 2010, 22, 3876–3892;
- 17cJ. L. Delgado, P.-A. Bouit, S. Filippone, M. Herranz, N. Martín, Chem. Commun. 2010, 46, 4853–4865;
- 17dG. Li, R. Zhu, Y. Yang, Nat. Photonics 2012, 6, 153–161.
- 18
- 18aA. Saeki, Y. Koizumi, T. Aida, S. Seki, Acc. Chem. Res. 2012, 45, 1193–1202;
- 18bA. Saeki, S. Seki, T. Takenobu, Y. Iwasa, S. Tagawa, Adv. Mater. 2008, 20, 920–923;
- 18cH. Hayashi, W. Nihashi, T. Umeyama, Y. Matano, S. Seki, Y. Shimizu, H. Imahori, J. Am. Chem. Soc. 2011, 133, 10736–10739;
- 18dY. Matano, H. Ohkubo, Y. Honsho, A. Saito, S. Seki, H. Imahori, Org. Lett. 2013, 15, 932–935.
