Issue 13, 2012

Structure, photophysics, and photooxidation of crowded diethynyltetracenes

Abstract

This paper describes a previously unreported class of sterically crowded tetracene derivatives that have both phenyl and ethynyl substituents. The steric crowding above and below the tetracene core prevents overlap between the extended π-systems of the acenes. Substituent effects cause these tetra-substituted tetracenes to have absorbance and fluorescence spectra red shifted from either disubstituted derivatives or rubrenes, such that they have spectra similar to diarylpentacenes, but with higher quantum yields of fluorescence and greater photostability. These new molecules also undergo cycloaddition reactions with 1O2, giving regioisomeric mixtures of endoperoxides, and in contrast to longer acenes, the ethynyl substituents show only a modest stabilizing effect to photooxidation. Ethynylated tetracenes also exhibited photochromism, with their endoperoxides undergoing cycloreversion to yield the acene starting material at room temperature in the dark.

Graphical abstract: Structure, photophysics, and photooxidation of crowded diethynyltetracenes

Supplementary files

Article information

Article type
Paper
Submitted
26 Nov 2011
Accepted
09 Feb 2012
First published
17 Feb 2012

J. Mater. Chem., 2012,22, 6182-6189

Structure, photophysics, and photooxidation of crowded diethynyltetracenes

J. Zhang, S. Sarrafpour, T. E. Haas, P. Müller and S. W. Thomas, J. Mater. Chem., 2012, 22, 6182 DOI: 10.1039/C2JM16173G

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