Multiresponsive spiropyran-based copolymer: synthesis and characterization

Abstract

Photochromic copolymers carrying spiropyran side groups have attracted particular attention for potential applications in optical devices, photonic memory and photosensing, as well as, fluorescence imaging.[1] These materials allow overcoming many of the limitations inherent to traditional spiropyran doped polymers, such as, phase separation of the colorant and retardation of the decoloration of the open form.[2] The introduction of light sensitive moieties within responsive polymers has led to the development of sophisticated multiresponsive systems.[3] Block copolymers are important self-assembling systems that can assume a diversity of nanometer-scale morphologies due to the incompatibility and the connectivity constrains between the chemically distinct segments. Therefore, self-assembly of photochromic copolymers in the solid state or in solution allows the development of nanostructured materials. [4] The aim of this research study is the synthesis of a multiresponsive spiropyran-based copolymer, poly(styrene)- co-poly([1´,3´,3´-trimethyl-6-methacryloyloxyspiro(2H-1-benzopyran-2,2´-indoline)]4-vinylbenzoic acid) 2. The functionalized block copolymer poly(styrene)-block-poly(4-vinylbenzoic acid) (PSt-b-P4VBA) 1 synthesized by reversible addition fragmentation chain-transfer (RAFT) polymerization was coupled with 1,3,3-trimethyl-6- hydroxyspiro(2H-1-benzopyran-2,2-indoline). The link between the functionalized block copolymer and spiropyran was successfully obtained by Steglich esterification using DMAP/DCC as catalysts (Scheme 1).