Our target in this work is to synthesize a polymer bearing a mussel-inspired Dopa-based catechol moiety. Naturally sesamol [3,4-(methylenedioxy)phenol] I has an electron-rich 1,3,4-triphenoxy motifs and based on our knowledge, the ring-opening reaction of epoxide built upon the triphenoxy motifs of hydroxyhydroquinone has not been studied. Sesamol I upon O-alkylation using epibromohydrin II has been converted to its epoxy monomer III. This monomer III underwent ring-opening polymerization using basic Bu4NOH and Bu4NF as well as by Lewis acid initiator/catalyst MePh3PBr/iBu3Al led to polyether IV. Monomer III and allyl glycidyl ether V have been randomly copolymerized to obtain copolymer VI, The pendant allyl groups in VI have been mutated via a thiol–ene reaction using cysteamine hydrochloride to give cationic (^^^NH3+) VII. To deprotection, the methylenedioxy (AOCH2OA) motifs in VII and get Dopa-based catechol moiety, the strategy is activated the methylenedioxy (AOCH2OA) motifs in VI by its conversion to labile acetoxymethylenedioxy [AOCH(OAc)OA] unit to obtain VIII. Then the pendant allyl groups in VIII upon elaboration via thiol-ene reaction using cysteamine hydrochloride and subsequent hydrolysis of [AOCH(OAc)OA] under a mild condition led to a mussel-inspired cationic copolymer IX having catechol motifs-embedded pendants of 3,4-dihydroxyphenoxy groups.

Ring-opening polymerization of natural sesamol based oxide and synthesis of mussel-inspired polymer

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