Communication

Crystal Structures and Electronic Properties of Saddle‐Distorted and Protonated Phthalocyanines^†

Department of Material and Life Science, Graduate School of Engineering, Osaka University, 2‐1 Yamada‐oka, Suita, Osaka 565‐0871 (Japan), Fax: (+81) 6879‐7370

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Prof. Dr. Takahiko Kojima

Corresponding Author

kojima@chem.tsukuba.ac.jp

Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba, 1‐1‐1 Tennoudai, Tsukuba, Ibaraki 305‐8571 (Japan)

Takahiko Kojima, Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba, 1‐1‐1 Tennoudai, Tsukuba, Ibaraki 305‐8571 (Japan)

Nagao Kobayashi, Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980‐8578 (Japan)

Shunichi Fukuzumi, Department of Material and Life Science, Graduate School of Engineering, Osaka University, 2‐1 Yamada‐oka, Suita, Osaka 565‐0871 (Japan), Fax: (+81) 6879‐7370

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Prof. Dr. Nagao Kobayashi

Corresponding Author

nagaok@m.tohoku.ac.jp

Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980‐8578 (Japan)

Takahiko Kojima, Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba, 1‐1‐1 Tennoudai, Tsukuba, Ibaraki 305‐8571 (Japan)

Nagao Kobayashi, Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980‐8578 (Japan)

Shunichi Fukuzumi, Department of Material and Life Science, Graduate School of Engineering, Osaka University, 2‐1 Yamada‐oka, Suita, Osaka 565‐0871 (Japan), Fax: (+81) 6879‐7370

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Prof. Dr. Shunichi Fukuzumi

Corresponding Author

fukuzumi@chem.eng.osaka‐u.ac.jp

Department of Material and Life Science, Graduate School of Engineering, Osaka University, 2‐1 Yamada‐oka, Suita, Osaka 565‐0871 (Japan), Fax: (+81) 6879‐7370

Department of Bioinspired Science, Ewha Womans University, Seoul 120‐750 (Korea)

Takahiko Kojima, Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba, 1‐1‐1 Tennoudai, Tsukuba, Ibaraki 305‐8571 (Japan)

Nagao Kobayashi, Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980‐8578 (Japan)

Shunichi Fukuzumi, Department of Material and Life Science, Graduate School of Engineering, Osaka University, 2‐1 Yamada‐oka, Suita, Osaka 565‐0871 (Japan), Fax: (+81) 6879‐7370

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Tatsuhiko Honda

Department of Material and Life Science, Graduate School of Engineering, Osaka University, 2‐1 Yamada‐oka, Suita, Osaka 565‐0871 (Japan), Fax: (+81) 6879‐7370

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Prof. Dr. Takahiko Kojima

Corresponding Author

kojima@chem.tsukuba.ac.jp

Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba, 1‐1‐1 Tennoudai, Tsukuba, Ibaraki 305‐8571 (Japan)

Takahiko Kojima, Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba, 1‐1‐1 Tennoudai, Tsukuba, Ibaraki 305‐8571 (Japan)

Nagao Kobayashi, Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980‐8578 (Japan)

Shunichi Fukuzumi, Department of Material and Life Science, Graduate School of Engineering, Osaka University, 2‐1 Yamada‐oka, Suita, Osaka 565‐0871 (Japan), Fax: (+81) 6879‐7370

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Prof. Dr. Nagao Kobayashi

Corresponding Author

nagaok@m.tohoku.ac.jp

Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980‐8578 (Japan)

Takahiko Kojima, Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba, 1‐1‐1 Tennoudai, Tsukuba, Ibaraki 305‐8571 (Japan)

Nagao Kobayashi, Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980‐8578 (Japan)

Shunichi Fukuzumi, Department of Material and Life Science, Graduate School of Engineering, Osaka University, 2‐1 Yamada‐oka, Suita, Osaka 565‐0871 (Japan), Fax: (+81) 6879‐7370

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Prof. Dr. Shunichi Fukuzumi

Corresponding Author

fukuzumi@chem.eng.osaka‐u.ac.jp

Department of Material and Life Science, Graduate School of Engineering, Osaka University, 2‐1 Yamada‐oka, Suita, Osaka 565‐0871 (Japan), Fax: (+81) 6879‐7370

Department of Bioinspired Science, Ewha Womans University, Seoul 120‐750 (Korea)

Takahiko Kojima, Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba, 1‐1‐1 Tennoudai, Tsukuba, Ibaraki 305‐8571 (Japan)

Nagao Kobayashi, Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980‐8578 (Japan)

Shunichi Fukuzumi, Department of Material and Life Science, Graduate School of Engineering, Osaka University, 2‐1 Yamada‐oka, Suita, Osaka 565‐0871 (Japan), Fax: (+81) 6879‐7370

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First published: 15 February 2011

https://doi.org/10.1002/anie.201006607

Citations: 34

^†

This work was supported by Grants‐in‐Aid (Nos. 21750146, 20108010 and 20108001), a Global COE program, “the Global Education and Research Center for Bio‐Environmental Chemistry” from the Japan Society of Promotion of Science (JSPS), the Ministry of Education, Science, and Technology of Japan, and by KOSEF/MEST through WCU project (R31‐2008‐000‐10010‐0).

Abstract

Protonation made easy: The formation and crystal structure determination of phthalocyanine protonated at the meso‐ and isoindole nitrogen atoms (see picture) are achieved by using the free base and a zinc complex of saddle‐distorted octaphenylphthalocyanine, respectively. The saddle deformation alters the electronic structure of the phthalocyanine ring and facilitates its protonation.