Electrochemical Switching of First-Generation Donor-Acceptor Stenhouse Adducts (DASAs): An Alternative Stimulus for Triene Cyclisation

Abstract

Donor-acceptor Stenhouse adducts (DASAs) are a photo-switch class that undergoes triene cyclisation in response to visible light. Herein, electrochemical oxidation is demonstrated as an effective alternative stimulus for the triene cyclisation commonly associated with photo-switching.

Visible light-responsive materials: the (photo)chemistry and applications of donor–acceptor Stenhouse adducts in polymer science

“…In addition, the versatility of spiropyran photoswitches being responsive to other stimuli than light, including thermo-, acido-, mechano-, solvato-, and electrochromic responsivity, was one of the reasons for their popularity and use in a variety of dynamic materials. Multi stimuliresponsiveness of DASAs was also explored, including metal ions, 69,103,112,[171][172][173] water, 101 acids/bases, 104,105 or electrochemistry, 174 which could present interesting opportunities also in polymer and material science in the future. Moreover, the large drop in T g and elastic modulus of polymers upon photoswitching of covalently attached DASAs could offer many opportunities for polymer phase transition control, 96 for example, for self-healing materials, smart adhesives or photorheological fluids.…”

Photoresponsive Metal-Organic Frameworks as Adjustable Scaffolds in Reticular Chemistry

“…Donor-acceptor Stenhouse adducts are a type of heterocyclic photoswitchable organic compound that experiences reversible triene cyclisation through the application of a photochemical stimulus (Figure 10), efficiently exchanging between open ring and closed ring forms [77].…”

“…Donor-acceptor Stenhouse adducts are a type of heterocyclic photoswitchable organic compound that experiences reversible triene cyclisation through the application of a photochemical stimulus (Figure 10), efficiently exchanging between open ring and closed ring forms [77]. Professor D'Alessandro and colleagues reported the postsynthetic modification of defect engineered MOFs to obtain DASA-functionalized crystalline porous materials [78].…”

Coordination Polymers and Metal-Organic Frameworks: Structures and Applications—A Themed Issue in Honor of Professor Christoph Janiak on the Occasion of His 60th Birthday

“…These represent a class of photoswitches that undergo light-initiated triene cyclization. However, D'Alessandro and coworkers have demonstrated that electrochemical oxidation is an effective alternative stimulus [11].…”