Synthesis and Spectroscopic Properties of 1,2,3-Triazole BOPAHY Dyes and Their Water-Soluble Triazolium Salts
Tomas Horsten, Flip de Jong, Dries Theunissen, Mark Van der Auweraer, Wim Dehaen
Abstract
Water-soluble BOPAHY fluorophores have not yet been reported. The potential of 1,2,3-triazolium salts for the formation of water-soluble chromophores is explored. 1,2,3-Triazole-substituted pyrroles were synthesized in a metal-free pathway and alkylated to obtain water-soluble 1,2,3-triazolium BOPAHY dyes. High fluorescence quantum yields were observed for triazole-bridged BOPAHY dyes in DCM and moderate fluorescence quantum yields for 1,2,3-triazolium-bridged BOPAHY chromophores in DCM and water. The fluorescence of the freely rotatable 1,2,3-triazolium-linked BOPAHYs is partially quenched in water.
Topics & Concepts
ChromophoreFluorescenceTriazoleChemistryWater solubleAlkylationPhotochemistry1,2,4-TriazoleMetalClick chemistryCombinatorial chemistryOrganic chemistryCatalysisPhysicsQuantum mechanicsLuminescence and Fluorescent MaterialsSupramolecular Self-Assembly in MaterialsPorphyrin and Phthalocyanine Chemistry