A chitosan-based chemomechanical polymer triggered by stacking effects with aromatic effectors including aminoacid derivatives

Abstract

Chitosan with a covalently attached anthrylunit is used as chemomechanical polymer, in which stacking and cation–π interactions allow aromatic effector compounds with positively charged nitrogen centers to trigger macroscopic motions in aqueous surrounding. Thus, only protonated heterocycles such as imidazole or histamine lead at pH 5 to expansion, in contrast to toluenesulfonic acid, or pyrazole and pyrimidine. Inorganic salts and pH influence the polymer swelling, and must be taken into account for the calculation of net effects induced by organic effectors. Reversible volume expansions on the top of the swelling effect of water alone are observed as function of different effector structures, showing, for example, 45% net effect with imidazole and 66% with benzimidazole. Aminoacids, for solubility reasons measured in the form of their methylesters, yield smaller expansions, showing, however, a regular and selective increase with the lipophilicity of the residues. The kinetics of effector uptake, which relates to the velocity of expansion, are measured with histamine and follow first order, with t 1/2=2.7 min for 50% absorption.