Synthesis of Triazolo[c]coumarins and Differences in the Fluorescence Properties of Their Isomers

Author:

Sekine Miyu1ORCID,Ishida Hiroaki1ORCID,Itoh Toshimasa1ORCID

Affiliation:

1. Showa Pharmaceutical University 3-3165, Higashi-Tamagawagakuen Machida city 194 8543 Tokyo Japan

Abstract

AbstractDespite the simple structures of 3,4‐fused tricyclo coumarins, their fluorescence properties have not been studied extensively. We have synthesized triazolo[c]coumarins using Huisgen cycloaddition and investigated their fluorescence properties. The Huisgen cycloaddition was found to proceed in excellent yields when subjected to heating under solvent‐free conditions. As is generally known, fluorescence is enhanced with an increase in the electron‐donating group at the 7‐position. The 7‐NEt2‐triazolo[c]coumarin derivatives showed useful fluorescence, and their relative fluorescence quantum yields in aprotic polar organic solvents were high. It revealed that fluorescence properties of triazolo[c]coumarins depended on the regio isomer. The electron distribution was hardly extended to alkyl side chain on triazole from the molecular orbital calculation by density functional theory (DFT) and time‐dependent DFT (TD‐DFT). This result suggests that the trend of fluorescence properties is similar to the present result even when various substituents are introduced on triazole.

Funder

Showa Pharmaceutical University

Publisher

Wiley

Subject

Organic Chemistry

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