Alcohol- and acid-causing reversible switching of near-infrared absorption and luminescence in a donor–acceptor conjugated system

Mio Kondo; Maai Uchikawa; Shoko Kume; Hiroshi Nishihara

doi:10.1039/B823248B

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Alcohol- and acid-causing reversible switching of near-infrared absorption and luminescence in a donor–acceptor conjugated system†

Mio Kondo,^a Maai Uchikawa,^a Shoko Kume^a and Hiroshi Nishihara*^a

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* Corresponding authors

^a Department of Chemistry, School of Science, The University of Tokyo, 7-3-1, Hongo, Bunkyo-Ku, Tokyo, Japan
E-mail: nisihara@chem.s.u-tokyo.ac.jp
Fax: +81 (0)3 5831 8063

Abstract

2-Substituted 7-oxo-7,11b-dihydrodibenzochromenilium derivatives (1-ArPyl⁺s) undergo reversible changes in near-infrared absorption when Ar = ferrocenyl, and complete on–off switching of luminescence when Ar = p-tolyl, m-tolyl, or phenyl, by the reaction with methanol or methoxide ion and with acid.

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Supplementary files

Details in determination of the structure of 1- p-TolPyl-OMe, experimental and calculated excitation energies to the lowest excited state for 1- p-TolPyl-OMe (Table S1), UV-Vis spectra of 1- p-TolPyl in different solvents (Fig. S1), UV-Vis spectra of 1- p-TolPyl in methanol and the isolated compound in reaction of 1- p-TolPyl and NaOMe, a ¹H NMR spectrum of 1- p-TolPyl-OMe (Fig. S3), the optimized molecular structure of 1- p-TolPyl-OMe (Fig. S4), molecular orbitals of 1- p-TolPyl-OMe (Fig. S5), UV-Vis-NIR spectra of 1-ArPyl ⁺ (Fig. S6), and the changes of absorbance at 536 nm of a 1- p-TolPyl ⁺ solution upon the alternate addition of TBACl and TFSIH (Fig. S7) PDF (850K)

Article information

DOI: https://doi.org/10.1039/B823248B
Article type: Communication
Submitted: 24 Dec 2008
Accepted: 03 Feb 2009
First published: 25 Feb 2009

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Chem. Commun., 2009, 1993-1995

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Alcohol- and acid-causing reversible switching of near-infrared absorption and luminescence in a donor–acceptor conjugated system

M. Kondo, M. Uchikawa, S. Kume and H. Nishihara, Chem. Commun., 2009, 1993 DOI: 10.1039/B823248B

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Chemical Communications

Alcohol- and acid-causing reversible switching of near-infrared absorption and luminescence in a donor–acceptor conjugated system†

Abstract

Supplementary files

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Alcohol- and acid-causing reversible switching of near-infrared absorption and luminescence in a donor–acceptor conjugated system

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