Substituent Effects Control Spiropyran-Merocyanine Equilibria and Mechanochromic Utility

Spiropyran (SP) derivatives can be converted into the colored merocyanine (MC) form using a variety of triggers. Optical switching by light for memories and dynamic systems is long known. Recently, mechanical force has been reported as an additional stimulus that converts SP into MC. SP-based mechanochromic systems are especially interesting for polymer scientists, as the covalent attachment of polymer chains is ideal to transduce force to the SP level. Whether such materials are investigated to better understand fundamental processes or long standing questions in polymer science, to design force sensors or to self-report damage, or simply pose fascinating materials which turn colored upon deformation, they have intrigued polymer scientists for more than a decade. With the chemistry of SPs being feasible and SP functionalization important to modulate SP/MC equilibria, a significant amount of work on SP structure- mechanochromic function relations has accumulated. SPs can be used as bifunctional initiators, cross-linkers, monomers, or be synthesized during polymerization. This feature article provides an overview of how the chemistry used sets the boundaries within which the mechanochromic response of SP containing polymers can be modulated.