Oligo(ethylene glycol) (OEG) functionalized 2-(2?-Hydroxy benzofuranyl) benzoxazole (HBBO) derivatives: Synthesis, photophysical properties and biomolecules binding studies

نویسندگان

چکیده

Two molecular fluorophores based on a 2-(2?-Hydroxybenzofuranyl) benzoxazole (HBBO) scaffold and presenting an Excited-State Intramolecular Proton Transfer (ESIPT) process are reported herein. These dyes incorporate strongly electrodonating aromatic amino groups the benzofuranyl side, enabling appearance of dual fluorescence emission corresponding to radiative decay excited enol (E*) keto (K*) tautomers at high low energy respectively. It was previously demonstrated that E*/K* could originate from beneficial decrease phenolic acidity upon absorption light leading thermodynamic stabilization first excited-state. The innovation within these lies in double functionalization aniline moiety with 2-(2-methoxyethoxy)ethyl units which allowed better solubilization protic solvents, as compared their butyl analogs while keeping strong capacity. Their intrinsic amphiphilic character leads good vectorization wide range solvents toluene PBS buffer. investigation photophysical properties solution showed clear apolar E* band gradually red-shifting along dipole moment solvent. Dual is also observed solid-state when doped 1% wt PMMA or PS films. Finally, interactions one dye calf-thymus (ct)-DNA Bovine Serum Albumin (BSA) have been explored reveal pronounced modifications UV–Vis profile dye. Additionally, gradual hypsofluorochromic shift narrowing K* addition ct-DNA BSA observed, presumably evidencing intercalation mode binding.

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ژورنال

عنوان ژورنال: Dyes and Pigments

سال: 2021

ISSN: ['1873-3743', '0143-7208']

DOI: https://doi.org/10.1016/j.dyepig.2020.108895