Improving the kinetics and dark equilibrium of donor–acceptor Stenhouse adduct by triene backbone design. Issue 14 (25th January 2022)

• Record Type: Journal Article
• Authors: Peterson, Julie A.; Stricker, Friedrich; Read de Alaniz, Javier
• Is Part Of: Chemical communications. Volume 58:Issue 14(2022)
• Page Start: 2303
• Page End: 2306
• Publication Date: 2022-01-25
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/d1cc06235b
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : DFT calculations were used to find an optimal substitution site on the triene backbone of a donor–acceptor Stenhouse adduct photoswitch to tune the equillibrium and switching kinetics of DASA without modifying the donor and acceptor groups. Abstract : DFT calculations were used to find an optimal substitution site on the triene backbone of a donor–acceptor Stenhouse adduct photoswitch to tune the equillibrium and switching kinetics of DASA without modifying the donor and acceptor groups. Using this approach we demonstrate a new means to tuning DASA based photoswitches by increasing the energy of the closed form relative to the open form. To highlight the potential of this approach a new DASA derivative bearing a methyl substituent on the 5-position of the triene was synthesized and the effect of this substitution was studied using 1 H NMR spectroscopy, time-dependent UV-Vis and solvatochromic analysis. The new DASA derivative shows a higher dark equillibrium, favoring the open form, and drastically faster thermal recovery than the unsubstituted derivative with the same donor and acceptor.