A cross-conjugation approach for high-performance diaryl-hemithioindigo photoswitches † † Electronic supplementary information (ESI) available. CCDC 2227014–2227018 and 2227451. For ESI and crystallographic data in CIF or other electronic format see DOI: https://doi.org/10.1039/d2sc06939c

ABSTRACT: Diaryl-hemithioindigos (diaryl-HTIs) are derivatives of a novel class of highly functionalized indigoid chromophores. In this work a systematic study of the electronic effects on their photoswitching reveals the design principles for achieving an excellent property profile. Two key elements need to be invoked for perfect diaryl-HTI performance, first introduction of strong electron donors and second establishment of cross-conjugation. The resulting photoswitches combine high thermal stability, large extinction coefficients, red-light responsiveness, pronounced photochromism, and strong isomer accumulation in the photostationary states with precise geometry changes. By using the inherent basicity of their strong electron donor moiety, diaryl-HTIs can be rendered into very potent tools for molecular logic applications. We demonstrate a variety of binary logic setups as well as sophisticated three- and four-input keypad locks for sequential logic operations. Three distinct states and up to four different stimuli are invoked for this multi-level molecular information processing. Diaryl-HTIs have thus entered the stage as very capable and promising photoswitch motives for anyone interested in reversible visible- and red-light as well as multi-stimuli responsive molecular behavior. A new class of diaryl-hemithioindigo is presented as capable reversible photoswitches with enhanced structural elaboration and stimuli-responsive behavior. Multi-state and multi-stimuli addressability enable advanced molecular logic operations.

SUBMITTER: Zitzmann M 

PROVIDER: S-EPMC10231315 | biostudies-literature | 2023 May

REPOSITORIES: biostudies-literature