Abstract
A new red hair-inspired 1,4-benzothiazine-based scaffold is disclosed herein, built upon a modular D-π-A architecture via condensation of the easily accessible 3-phenyl-2H-1,4-benzothiazine with indole-3-carboxaldehyde. The compound was obtained in around 50% yields and was characterized by complete spectroscopic analysis. The new benzothiazine-based cyanine displayed a characteristic reversible acidichromic behavior with a marked bathochromic shift upon acidification. The chromophore resisted at least fifteen hydrochloric acid/sodium hydroxide cycles without appreciable alterations. The expedient and scalable synthetic procedure together with the pH sensitive chromophoric properties would make the new compound an attractive prototype for novel modular chromophore for pH-sensing and other applications.
Highlights
The design and build-up of organic-based chromophores exhibiting tailored electronic and optical features has become an active research field over the past decade
Particular interest has been focused on optoelectronics [1,2,3,4,5], organic electronics, such as organic semiconductors [6,7,8,9], imaging technologies [10], and biomedicine [11,12,13,14,15,16,17]
An interesting nature-inspired class of compounds featuring most of the requisites for technological applications are cyanine dyes, which are structurally related to the betacyanin pigments occurring in fruits and vegetables and exhibiting red purple chromophores
Summary
The design and build-up of organic-based chromophores exhibiting tailored electronic and optical features has become an active research field over the past decade. An interesting nature-inspired class of compounds featuring most of the requisites for technological applications are cyanine dyes, which are structurally related to the betacyanin pigments occurring in fruits and vegetables and exhibiting red purple chromophores. These dyes feature an imine and an enamine type site arranged to form a push-pull system. Because of their excellent photophysical properties, such as high molar extinction coefficients and high fluorescence quantum yields, outstanding biocompatibility, and low toxicity to living systems, cyanines are good candidates for developing chemosensors [23,24,25,26]
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