Solid-State Luminescence with a Large Stokes Shift in Starch Functionalized with Low-Content ESIPT Dye

Abstract

Herein, we present the preparation of solid-state photoactive starches with a large Stokes shift, along with the resulting materials. In this investigation, 2-(2′-hydroxyphenyl)benzazole derivatives responsive to intramolecular proton transfer in the excited state (ESIPT) were covalently bonded to the polymeric structure of starch through a reaction involving an isothiocyanate group and the hydroxyl groups of starch. These compounds exhibit absorption at approximately 350 nm, which is related to fully spin- and symmetry-allowed π → π* electronic transitions, and solid-state fluorescence at approximately 500 nm, which features a significant separation between the absorption and emission maxima (~9000 cm−1). Due to the minimal use of fluorophores in functionalized starch preparation, this modification does not affect the original properties of the starch. Finally, photoactive starch-based films with significantly high transparency were successfully produced.

Keywords

• photoactive starch
• ESIPT
• large Stokes shift
• biodegradable polymer
• tagging material