Efficient And Ambient Esterification Of Poly(Ethyl Bromide Methacylate) And Carboxyl Compounds For Bioconjugation

Efficient and ambient synthesis of polymer-small molecule conjugate has been a significant goal of polymer chemistry. Recently, Bai et al. reported an ambient and high efficient(almost 100%) esterification reactions between poly [(meth) acrylic acid] and a series of halides in the presence of 1, 1, 3, 3-tetramethyl guanidine(TMG) Inspired by their method, in this thesis, we designed and synthesized a serials of polymer-small molecule conjugates by esterification of halide containing polymers and carboxyl compounds using TMG as catalyst. This thesis is mainly divided into three parts :(1) Firstly, we designed and synthesized homopolymer poly [ethyl bromide(meth) acrylate] by radical polymerization of new synthetic monomer ethyl bromide(meth) acrylate.(2) Secondly, we conjugated the halide containing polymers with carboxyl compounds(such as benzoic acid, nicotinic acid, aspirin, 1-Adamantanecarboxylic acid, lactic acid, et al.)in the presence of 1, 1, 3, 3-tetramethyl guanidine(TMG) and obtained a groups of new poly(meth)acrylate; Finally, we conjugated the halide containing polymers with both benzoic acid and lactic acid in the presence of TMG with tuning the ratio of these two carboxyl compounds and obtained a serials of poly(meth)acrylate from water soluble to amphiphilic. The self-assemble property of amphiphilic random copolymers in aqueous solution was also studied.Finally, we conjugated the halide containing polymers with both benzoic acid and lactic acid in the presence of TMG with tuning the ratio of these two carboxyl compounds and obtained a serials of poly(meth)acrylate from water soluble to amphiphilic. The self-assemble property of amphiphilic random copolymers in aqueous solution was also studied.