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Issue 66, 2016, Issue in Progress
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Unusual blue-shifted acid-responsive photoluminescence behavior in 6-amino-8-cyanobenzo[1,2-b]indolizines

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Abstract

6-Amino-8-cyanobenzo[1,2-b]indolizines, a new class of photoluminescent materials, exhibit reversible pH-dependent optical properties characterized by an uncommon and dramatic blue shift in fluorescence emission when protonated. Acid titration and NMR spectroscopy experiments reveal that, rather than the anticipated N-protonation, C-protonation and loss of aromaticity is responsible for the observed photophysical changes. Efficient synthesis from indole-2-carboxaldehydes makes variously substituted versions of this nucleus readily available to tune optical and pH effects.

Graphical abstract: Unusual blue-shifted acid-responsive photoluminescence behavior in 6-amino-8-cyanobenzo[1,2-b]indolizines

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Article information


Submitted
24 Apr 2016
Accepted
02 Jun 2016
First published
03 Jun 2016

RSC Adv., 2016,6, 61249-61253
Article type
Communication

Unusual blue-shifted acid-responsive photoluminescence behavior in 6-amino-8-cyanobenzo[1,2-b]indolizines

V. K. Outlaw, J. Zhou, A. E. Bragg and C. A. Townsend, RSC Adv., 2016, 6, 61249
DOI: 10.1039/C6RA10605F

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