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Issue 20, 2013
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The formation of peroxide degradation products of photochromic triphenylimidazolyl radical-dimers

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Abstract

Following the recent report of Abe and co-workers (Phys. Chem. Chem. Phys., 2012, 14, 5855) of the isolation of a bridging peroxide of a naphthalene-tethered bisimidazolyl diradical, it is reported herein that this degradation pathway is a more general phenomenon for the chromic dimers of 2,4,5-triphenylimidazolyl radical (TPIR) materials, with non-tethered TPIRs forming similar oxygen adducts. The peroxides of two derivatives have been characterised by single crystal X-ray diffraction (SC-XRD) and it is identified that the 4-position of the imidazolyl ring is the site susceptible to reaction with oxygen. Furthermore, mass spectrometry has been used to show that for a range of five known, non-tethered derivatives, peroxide formation can be detected within 30 minutes when samples are irradiated under an oxygen atmosphere, thus presenting a significant challenge to the long term use of this class of material in colour-switching device applications.

Graphical abstract: The formation of peroxide degradation products of photochromic triphenylimidazolyl radical-dimers

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Supplementary files

Article information


Submitted
19 Feb 2013
Accepted
11 Apr 2013
First published
12 Apr 2013

Phys. Chem. Chem. Phys., 2013,15, 7848-7853
Article type
Paper

The formation of peroxide degradation products of photochromic triphenylimidazolyl radical-dimers

R. M. Edkins, M. R. Probert, K. Fucke, C. M. Robertson, J. A. K. Howard and A. Beeby, Phys. Chem. Chem. Phys., 2013, 15, 7848
DOI: 10.1039/C3CP50757B

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