Water soluble photoactive cellulose derivatives: synthesis and characterization of mixed 2-[(4-methyl-2-oxo-2H-chromen-7-yl)oxy]acetic acid–(3-carboxypropyl)trimethylammonium chloride esters of cellulose

摘要

Photoactive derivatives of cellulose were prepared by a mild esterification of the biopolymer with 2-[(4-methyl-2-oxo-2H-chromen-7-yl)oxy]acetic acid via the activation of the carboxylic acid with N,N′-carbonyldiimidazole. Subsequently, modification with the cationic carboxylic acid (3-carboxypropyl)trimethylammonium chloride was carried out. Thus, water soluble polyelectrolytes decorated with high amounts of photochemically active chromene moieties were obtained. The structures of the novel polysaccharide esters and the polyelectrolytes were evaluated by means of NMR and IR spectroscopy. Moreover, the light triggered photodimerization of the chromene moieties of the photoactive polyelectrolytes was studied by means of UV–Vis spectroscopy in the dissolved state. The photochemistry observed may be used to control the properties of the new polysaccharide derivatives and are thus of interest in the design of smart materials.