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

• Published in: Cellulose (London) 2012-08, Vol.19 (4), p.1327-1335
• Main Authors: Wondraczek, Holger, Pfeifer, Annett, Heinze, Thomas
• Format: Article
• Language: English
• Subjects: Acetic acid; Acids; Bioorganic Chemistry; Biopolymers; Carbonyls; Cellulose; Cellulose esters; Ceramics; Chemistry; Chemistry and Materials Science; Composites; Derivatives; Esterification; Esters; Glass; Infrared spectroscopy; Natural Materials; NMR; Nuclear magnetic resonance; Organic Chemistry; Original Paper; Photochemistry; Physical Chemistry; Polyelectrolytes; Polymer Sciences; Polysaccharides; Smart materials; Spectrum analysis; Sustainable Development; Water chemistry
• ISSN: 0969-0239; 1572-882X
• DOI: 10.1007/s10570-012-9708-2

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.