Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 61, Issue 41, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202209441
Keywords
Chalcogen; Cyclic Azobenzene; Energy Conversion; Ring-Strain; TD-DFT
Categories
Funding
- National Natural Science Foundation of China [21973066, 22001181, 22077090]
- Fundamental Research Funds for the Central Universities [20826041D4117]
- Institutional Research Fund from Sichuan University [2020SCUNL105]
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Three strategies, including tetra-ortho-substituted, heteroaryl, and cyclic azobenzenes, have been used to design the morphology of photoswitches for increased controllability. In this study, a family of dibenzo[b,f][1,4,5]chalcogenadiazepines (DBChDs) with tunable relaxation rates were reported. An unsymmetric 2-bithiophenyl-dibenzo[b,f][1,4,5]thiadiazepine showed efficient photo-switching properties in response to 445 nm laser stimulation.
Tetra-ortho-substituted, heteroaryl and cyclic azobenzenes have emerged as three key strategies on morphology design of photoswitch to diversify controllability. Cyclic azobenzene is of particular utilization in photo-energy conversion due to rigid and ring-strain structure. Despite the well-recognized diazocine, the photo-switching properties of seven-membered cyclic azobenzenes (diazepines) have yet been exploited. Herein, we report a family of dibenzo[b,f][1,4,5]chalcogenadiazepines (DBChDs) and their T-type photo-switching nature with tunable relaxation rate. Based on experiments together with DFT calculations, we found that an unsymmetric 2-bithiophenyl-dibenzo[b,f][1,4,5]thiadiazepine exhibited an efficient response to 445 nm laser stimulation (quantum efficiency, phi(Z -> E)=0.71) with millisecond relaxation half-life (t(1/2)=40 ms). Photo-energy transduction efficiency was also exceptionally high with 29.1 % converted into ring-strain energy mainly loaded on azo pi-bond.
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