Fluorescence of Hydroxyphenyl-Substituted "Click" Triazoles

The Journal of Physical Chemistry. a
Quinton J MeisnerLei Zhu

Abstract

The structural and optical properties of hydroxyphenyl-substituted-1,2,3-triazole molecules ("click" triazoles) are described. "Click" triazoles are prepared from the copper(I)-catalyzed azide-alkyne cycloaddition reactions. The alkyne-derived C4 substituent of a "click" triazole engages in electronic conjugation more effectively with the triazolyl core than the azide-derived N1 substituent. Furthermore, triazolyl group exerts a stronger electron-withdrawing effect on the N1 than the C4 substituent. Therefore, the placement of an electron-donating group at either C4 or N1 position and the presence or the absence of an intramolecular hydrogen bond (HB) have profound influences on the optical properties of these compounds. The reported "click" triazoles have fluorescence quantum yields in the range of 0.1-0.3 and large apparent Stokes shifts (8000-13 000 cm-1) in all tested solvents. Deprotonation of "click" triazoles with a C4 hydroxyphenyl group increases their Stokes shifts; while the opposite (or quenching) occurs to the triazoles with an N1 hydroxyphenyl substituent. For the triazoles that contain intramolecular HBs, neither experimental nor computational results support a model of excited state intramolecular proton transfe...Continue Reading

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Citations

Oct 18, 2018·Organic & Biomolecular Chemistry·Qi LaiZhiguang Song
Jun 30, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Natalia A DanilkinaIrina A Balova
Feb 16, 2021·ACS Omega·Joseph J M HurleyLei Zhu
Nov 10, 2018·The Journal of Physical Chemistry. a·Quinton J MeisnerLei Zhu

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