Excited-state intramolecular proton transfer (ESIPT) emitters based on a 2-(2′-hydroxybenzofuranyl)benzoxazole (HBBO) scaffold functionalised with oligo(ethylene glycol) (OEG) chains. (29th May 2019)

• Record Type: Journal Article
• Authors: Felouat, Abdellah; Curtil, Mathieu; Massue, Julien; Ulrich, Gilles
• Is Part Of: New journal of chemistry. Volume 43:Number 23(2019)
• Page Start: 9162
• Page End: 9169
• Publication Date: 2019-05-29
• Subjects: Chemistry -- Periodicals; Chimie -- Périodiques; 540
• DOI: 10.1039/c9nj00809h
• Languages: English
• ISSNs: 1144-0546

Abstract

Abstract : This article describes the multi-step synthesis of 2-(2′-hydroxybenzofuran)benzoxazole (HBBO) derivatives functionalised with one to three oligo(ethylene glycol) (OEG) chains with the goal to allow a good vectorization in aqueous media. Abstract : This article describes the multi-step synthesis of 2-(2′-hydroxybenzofuran)benzoxazole (HBBO) derivatives functionalised with one to three oligo(ethylene glycol) (OEG) chains with the goal to allow a good vectorization in aqueous media. Benzoxazole dyes are well-known organic fluorophores exhibiting excited-state intramolecular proton transfer (ESIPT) emission. The insertion of these highly hydrophilic OEG chains allows a good solubilization of these dyes in a wide range of solvents of different polarity including PBS buffer/DMSO (95/5) and water, for one of them. The photophysical properties of these ESIPT emitters in solution, and also in the solid-state, as doped as 1 wt% in poly(methylmethacrylate) (PMMA) or polystyrene (PS) films, are discussed. Specifically, the presence of an OEG chain at the 3-position of the benzofuran ring was found to sizeably enhance the fluorescence intensity of the ESIPT emission in the solution state.