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Photoactive glycoconjugates with a very large Stokes shift: synthesis, photophysics, and copper(II) and BSA sensing.

Cláudia Brito da SilvaLuana SilvaNatalí Pires DebiaOtávio Augusto ChavesDiogo Seibert LüdtkeFabiano Severo Rodembusch
Published in: Organic & biomolecular chemistry (2023)
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 Cu 2+ 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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