Rotamer-Controlled Dual Emissive & alpha;-Amino Acids

The synthesis and photoluminescent properties of novel & alpha;-aminoacids are described in which the biaryl benzotriazinone-containingchromophores were found to display dual emission fluorescence vialocally excited (LE) and twisted intramolecular charge transfer (TICT)states. The intensity of each emission band could be controlled bythe electronics and position of the substituents, and this led tothe design of a 2-methoxyphenyl analogue that, due to twisting, displayedbright TICT fluorescence, solvatochromism, and pH sensitivity.

Automated summary

This article describes the synthesis and photoluminescent properties of novel α-amino acids, in which the chromophores containing biaryl benzotriazinone exhibit dual emission fluorescence through locally excited (LE) and twisted intramolecular charge transfer (TICT) states. The intensity of each emission band can be controlled by the electronics and position of the substituents, and this led to the design of a 2-methoxyphenyl analogue that, due to twisting, displays bright TICT fluorescence, solvatochromism, and pH sensitivity.