Synthesis and characterisation of fluorescent chitosan derivatives containing substituted naphthalimides

• Published in: Reactive & functional polymers Vol. 68; no. 3; pp. 671 - 678
• Main Authors: Munro, Natasha H., Hanton, Lyall R., Robinson, Brian H., Simpson, James
• Format: Journal Article
• Language: English
• Published: Amsterdam Elsevier B.V 01.03.2008; Elsevier Science
• Subjects: Acetic acid; Anhydrides; Applied sciences; Buffer solutions; Chitosan; Derivatives; Exact sciences and technology; Fluorescence; Molecular weight; Naphthalimide; Natural polymers; Nucleophiles; Physicochemistry of polymers; Starch and polysaccharides; β-chitin; Fluorescence; Naphthalimide; β-chitin; Chitosan; Pyridine derivative polymer; Bromine containing copolymer; Organic anhydride; Experimental study; Naphthalene derivatives; Pyridine derivatives; Chemical modification; Chitosan derivatives; Fluorescent material; Imidation; Preparation; Oside polymer; Aqueous solution; Nucleophilic substitution; Secondary amine; Heterogeneous reaction
• ISSN: 1381-5148
• DOI: 10.1016/j.reactfunctpolym.2007.11.003

Chitosan, derived from β-chitin, was reacted with 4-bromonaphthalic anhydride to produce a new chitosan derivative N-(4-bromonaphthalimide)-chitosan. The degree of substitution and molecular weight of the products were dependent upon the reaction conditions. The new chitosan polymer was reacted with the nucleophiles dimethylamine, piperidine and methoxide to produce substituted N-naphthalimide-chitosan derivatives. The materials were characterised by microanalyses, IR, GPC, 1H NMR, UV–vis and fluorescence spectroscopy. All four new polymers were fluorescent in acetic acid buffer solution and the nature of the fluorescence was dependent on the substituent.