Effect of indoline substitution on ring opening in 6-nitro BIPS spiropyran derivatives
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2024
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Palasis, K.A.
Abell, A.D.
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Tetrahedron Letters: the international journal for the rapid publication of all preliminary communications in organic chemistry, 2024; 138:154967-1-154967-5
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Kathryn A. Palasis; Andrew D. Abell
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Abstract
Spiropyrans constitute an important class of photoswitchable compound that have been studied in a variety of applications, including nanomaterials and biological sensing. However, many reported spiropyrans are impractical for these contexts due to a low quantum yield of switching, particularly in the ring opening direction. In this work, we report a series of spiropyrans substituted at the 5-indoline position of 6-NO2-BIPS, as a means to understand the electronic effects of substitution at this position on photochromism. Analysis of 1 H NMR spectra reveals that switching is greatest for the spiropyran with the most electron donating group at the 5-position. These findings inform the design of new spiropyran derivatives with improved switching to facilitate their use as functional switches.
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© 2024 The Author(s). Published by Elsevier Ltd. This is an open access article under the CC BY license (http://creativecommons.org/licenses/by/4.0/).