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Simultaneous fluorescence and redox modulation in an irreversible photochrome based on a strained dibenzo-acridinium cation

Lookup NU author(s): Professor Andrew Benniston, Dorota Rewinska

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Abstract

A highly strained non-luminescent dibenzo-acridinium cationic compound was identified in acetonitrile light-induced ring closure to create a highly fluorescent, planar, eight-ringed cationic anti-aromatic dye. It was found that the non-emissive compound upon illumination with white light ring closes to generate the highly fluorescent cation. Signals associated with the final product were visible and the other signals were clearly diminished, after a substantial irradiation time. The excitation and absorption spectra were in good agreement and the small Stokes shift indicated a modest change in structure after relaxation from the initially produced Franck-Condon state. The reduction portion of the cyclic voltammogram was dominated by a reversible one-electron wave, an irreversible one-electron wave, and and irreversible two-electron wave. The results show that light-induced ring closure effectively modulates its luminescent and redox properties in a highly-strained acridinium cation.

Publication metadata

Author(s): Benniston AC, Rewinska DB

Publication type: Article

Publication status: Published

Journal: Organic and Biomolecular Chemistry

Year: 2006

Volume: 4

Issue: 21

Pages: 3886-3888

Print publication date: 01/01/2006

ISSN (print): 1477-0520

ISSN (electronic): 1477-0539

Publisher: Royal Society of Chemistry

URL: http://dx.doi.org/10.1039/b611092d

DOI: 10.1039/b611092d

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