Unusual Blue-Shifted Acid-Responsive Photoluminescence Behavior in 6-Amino-8-cyanobenzo[1,2- b ]indolizines

6-Amino-8-cyanobenzo[1, 2- ]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 th...

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Bibliographic Details
Published inRSC advances Vol. 6; no. 66; pp. 61249 - 61253
Main Authors Outlaw, Victor K, Zhou, Jiawang, Bragg, Arthur E, Townsend, Craig A
Format Journal Article
LanguageEnglish
Published England 01.01.2016
Subjects
Aromaticity
Blue shift
Fluorescence
NMR spectroscopy
Optical properties
Photoluminescence
Synthesis
Titration
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Summary:6-Amino-8-cyanobenzo[1, 2- ]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.
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ISSN:2046-2069
2046-2069
DOI:10.1039/c6ra10605f