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Updated: Jul 11, 2025

Design, Synthesis, and Photochemical Properties of Clickable Caged Compounds
Published on: October 15, 2019
Photoactive glycoconjugates with a very large Stokes shift: synthesis, photophysics, and copper(II) and BSA sensing
Cláudia Brito da Silva1, Luana Silva2, Natalí Pires Debia2
1Grupo de Pesquisa em Fotoquímica Orgânica Aplicada. Instituto de Química (UFRGS), Av. Bento Gonçalves, 9500, CEP 91501-970, Porto Alegre, RS, Brazil. rodembusch@iq.ufrgs.br.
Abstract:
This study presents the synthesis of novel glycoconjugates by connecting benzazole and carbohydrate units with a 1,2,3-triazole linker. A simple synthetic route employing a copper(I) catalyzed azide-alkyne 1,3-dipolar cycloaddition (CuAAC) was utilized. The synthesized compounds exhibit excited-state intramolecular proton transfer (ESIPT), resulting in longer wavelength emission with a significantly large Stokes shift (∼10 000 cm-1). These compounds show potential as chemical sensors due to their ability to detect Cu2+ ions, causing a decrease in fluorescence emission (turn-off effect). Additionally, they demonstrate strong interaction with proteins, exemplified by their interaction with bovine serum albumin (BSA) as a model protein.
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