Volume 48, Issue 13 p. 2388-2390
Communication

Zwitterionic Corroles: Regioselective Nucleophilic Pyridination of a Doubly Linked Biscorrole

Satoru Hiroto

Department of Applied Chemistry, Graduate School of Engineering, Nagoya University, Nagoya 464‐8603 (Japan), Fax: (+81) 52‐789‐5113

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Naoki Aratani Dr.

Department of Chemistry, Graduate School of Science, Kyoto University, Kyoto 606‐8502 (Japan), Fax: (+81) 75‐753‐3970

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Naoki Shibata Prof. Dr.

Graduate School of Life Science, University of Hyogo, Hyogo 678‐1297 (Japan)

The RIKEN Spring‐8 Center, Hyogo 678‐5248 (Japan)

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Yoshiki Higuchi Prof. Dr.

Graduate School of Life Science, University of Hyogo, Hyogo 678‐1297 (Japan)

The RIKEN Spring‐8 Center, Hyogo 678‐5248 (Japan)

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Takahiro Sasamori Dr.

Institute for Chemical Research, Kyoto University, Kyoto 611‐0011 (Japan)

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Norihiro Tokitoh Prof. Dr.

Institute for Chemical Research, Kyoto University, Kyoto 611‐0011 (Japan)

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Hiroshi Shinokubo Prof. Dr.

Department of Applied Chemistry, Graduate School of Engineering, Nagoya University, Nagoya 464‐8603 (Japan), Fax: (+81) 52‐789‐5113

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Atsuhiro Osuka Prof. Dr.

Department of Chemistry, Graduate School of Science, Kyoto University, Kyoto 606‐8502 (Japan), Fax: (+81) 75‐753‐3970

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First published: 10 March 2009
Citations: 12

This work was partly supported by Grants‐in‐Aid for Scientific Research (nos. 18685013, 19205006, and 20037034) from the Ministry of Education, Culture, Sports, Science, and Technology (Japan). H.S. acknowledges Ogasawara Science Foundation for financial support. S.H. acknowledges the Research Fellowships of the JSPS for Young Scientists.

Abstract

Pyridine attacks: Nucleophilic addition of pyridine derivatives to a doubly linked corrole, which is a stable singlet biradical species, occurs at the bay area with high regioselectivity to provide zwitterionic dimers (see picture; Ar=C6F5). Charge transfer between the anionic corrole and the pyridinium groups induces effective fluorescence quenching of the corrole dimer, which can be utilized for selective fluoride ion recognition.

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