Photochromic biomaterials: Synthesis and fluorescence properties of spiroxanthenes-grafted alginate derivatives

Abstract

Herein, we reported a general and green synthetic strategy for photochromic functional alginate derivatives grafting with isoindolinone spiroxanthenes. Under mild condition, diverse 2-aminoalkyl isoindolinone spiroxanthene derivatives have been prepared from organic photochromic isobenzofuranone spiroxanthenes (including rhodamine B, rhodamine 6G and fluorescein), and grafted on alginate chains through amidation reaction using diamine as a linkage with water as a green solvent at room temperature. The photochromic properties of the fluorophores-modified polymers and the effect of pH value have been explored. Under acid conditions, the spiroisoindolinone rings of alginate derivatives are opened resulting in showing absorption bands and fluorescence with orange to green emission, while the alginate derivatives turned to colourless under basic conditions which is reversibly. In addition to biodegradability and biocompatibility, the polymers exhibit good film-forming properties simultaneously. The films and fibers produced from the alginate derivatives also project good fluorescence properties.