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Issue 33, 2012
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Antioxidant-substituted tetrapyrazinoporphyrazine as a fluorescent sensor for basic anions†‡§

Jonathan P. Hill,*ab   Navaneetha K. Subbaiyan,c   Francis D’Souza,*c   Yongshu Xie,*d   Satyajit Sahu,e   Noelia M. Sanchez-Ballester,a   Gary J. Richards,af   Toshiyuki Morif  and  Katsuhiko Arigaab  
Author affiliations

* Corresponding authors

a WPI-Centre for Materials Nanoarchitectonics, National Institute of Materials Science (NIMS), Namiki 1-1, Tsukuba, Ibaraki, Japan
E-mail: Jonathan.Hill@nims.go.jp
Tel: +81-(0)-29-8604832

b JST-CREST, Namiki 1-1, Tsukuba, Japan

c Department of Chemistry, University of North Texas, 1155, Union Circle, Denton, USA
E-mail: francis.dsouza@unt.edu
Tel: 940-369-8832

d Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, Meilong Rd. 130, Shanghai 200237, P. R. China
E-mail: yshxie@ecust.edu.cn

e Surface Characterization Group, Advanced Key Technologies Division/Nano Characterization Unit, National Institute of Materials Science (NIMS), Namiki 1-1, Tsukuba, Ibaraki, Japan

f Fuel Cell Materials Center, National Institute for Materials Science (NIMS), 1-1 Namiki, Tsukuba, Japan

Abstract

Tetrapyrazinoporphyrazine substituted at its periphery with eight antioxidant 3,5-di-t-butyl-4-hydroxyphenyl groups behaves as a turn-on fluorescent sensor for fluoride anions. Conversely, the precursor antioxidant-substituted 1,2-phthalonitrile was found to act in turn-off mode suggesting that the origin of the phenomenon lies at the phenolate-substituted 1,4-pyrazinyl moiety.

Graphical abstract: Antioxidant-substituted tetrapyrazinoporphyrazine as a fluorescent sensor for basic anions

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Article information

Submitted
01 Feb 2012
Accepted
22 Feb 2012
First published
27 Feb 2012
Chem. Commun., 2012,48, 3951-3953
Article type
Communication
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Antioxidant-substituted tetrapyrazinoporphyrazine as a fluorescent sensor for basic anions

J. P. Hill, N. K. Subbaiyan, F. D’Souza, Y. Xie, S. Sahu, N. M. Sanchez-Ballester, G. J. Richards, T. Mori and K. Ariga, Chem. Commun., 2012, 48, 3951
DOI: 10.1039/C2CC30712J

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