Photoisomerization of Arylazopyrazole Photoswitches: Stereospecific 
Excited-State Relaxation

Wang, Ya-Ting; Liu, Xiang-Yang; Cui, Ganglong; Fang, Wei-Hai; Thiel, Walter

doi:10.1002/anie.201607373

Item

ITEM ACTIONSEXPORT

Add to Basket

Local TagsRelease HistoryDetailsSummary

Released

Journal Article

Photoisomerization of Arylazopyrazole Photoswitches: Stereospecific Excited-State Relaxation

MPS-Authors

/persons/resource/persons59045

Thiel, Walter
Research Department Thiel, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

External Resource

No external resources are shared

Fulltext (restricted access)

There are currently no full texts shared for your IP range.

Fulltext (public)

There are no public fulltexts stored in PuRe

Supplementary Material (public)

anie201607373-sup-0001-misc_information.pdf
(Supplementary material), 3MB

Citation

Wang, Y.-T., Liu, X.-Y., Cui, G., Fang, W.-H., & Thiel, W. (2016). Photoisomerization of Arylazopyrazole Photoswitches: Stereospecific Excited-State Relaxation. Angewandte Chemie International Edition, 55(45), 14009-14013. doi:10.1002/anie.201607373.

Cite as: https://hdl.handle.net/11858/00-001M-0000-002C-00C2-B

Abstract

Electronic structure calculations and nonadiabatic dynamics simulations (more than 2000 trajectories) are used to explore the Z–E photoisomerization mechanism and excited-state decay dynamics of two arylazopyrazole photoswitches. Two chiral S₁/S₀ conical intersections with associated enantiomeric S₁ relaxation paths that are barrierless and efficient (timescale of ca. 50 fs) were found. For the parent arylazopyrazole (Z8) both paths contribute evenly to the S₁ excited-state decay, whereas for the dimethyl derivative (Z11) each of the two chiral cis minima decays almost exclusively through one specific enantiomeric S1 relaxation path. To our knowledge, the Z11 arylazopyrazole is thus the first example for nearly stereospecific unidirectional excited-state relaxation.