Novel Carbazole (Cbz)-Based Carboxylated Functional Monomers: Design, Synthesis, and Characterization

A series of novel functional carbazole (Cbz)-based carboxylated monomers were synthesized and characterized. A Clauson-Kaas procedure, a deprotection step, amide coupling, and hydrolysis were utilized as key chemical reactions towards the multistep synthesis of monomers in good to excellent isolated yields. The design strategy was further extended to complex carbazole-COOH monomers incorporated arylazo groups as photoreactive moieties. In addition, photoreactive hybrid carbazole (Cbz)-pyrrole (Pyr)-based carboxylated monomers, comprising a pyrrole core linking a carbazole and a photoreactive phenylazide or benzophenone moiety through an amide spacer in the molecular structure, were also synthesized. The latter can be utilized for surface modification of polymeric films in their monomeric form or as polymeric microparticles (MPs). Functional monomers: Novel functional carbazole-based carboxylated monomers were accessed using a Clauson-Kaas procedure, a deprotection step, amide coupling, and hydrolysis in a multistep synthesis. The design strategy was extended to complex carbazole-COOH monomers incorporating arylazo and phenylazide or benzophenone as photoreactive moieties, which can be utilized for functionalization/decoration of various polymeric and non-polymeric surfaces, matrices, and non-functional nanomaterials in their monomeric states or as polymeric microparticles (MPs).