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Coumarin Photocaging Groups Modified with an Electron‐Rich Styryl Moiety at the 3‐Position: Long‐Wavelength Excitation, Rapid Photolysis, and Photobleaching
Author(s) -
Lin Qiuning,
Yang Lipeng,
Wang Zhiqiang,
Hua Yujie,
Zhang Dasheng,
Bao Bingkun,
Bao Chunyan,
Gong Xueqing,
Zhu Linyong
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201800713
Subject(s) - moiety , photochemistry , chemistry , carbocation , photobleaching , conjugated system , triphenylamine , intramolecular force , fluorescence , stereochemistry , organic chemistry , polymer , physics , quantum mechanics
A new class of coumarin photocaging groups modified with an electron‐rich styryl moiety at the 3‐position was constructed. The large π‐conjugated structure and stabilization of the carbocation intermediates by electron donors endowed the new photocaging groups with excellent long‐wavelength absorption, large two‐photon absorption cross‐sections, and high uncaging quantum yields. Moreover, the new photocaging groups displayed unique photobleaching properties after photocleavage as a result of the intramolecular cyclization rearrangement of a carbocation intermediate to form five‐membered ring byproducts and block the styryl conjugation at the 3‐position. These superior properties of the new photocaging groups are extremely beneficial for high‐concentration samples and thick specimens, thus extending the application of photocaging groups in many fields.