Sequential control over thiol click chemistry by a reversibly photoactivated thiol mechanism of spirothiopyran.
A novel photocontrolled thiol click chemistry based on spirothiopyran and maleimide is reported. Upon irradiation with λ=365 nm light, the spirothiopyran can isomerize to the open merocyanine form, a thiophenolate group, which can rapidly react with maleimide. The unreacted MC will readily isomerize back to the starting spirothiopyran, which can be repeatedly photoactivated as needed. Thus, this reversible photoactivated thiol confers spatiotemporal sequential control on the thiol-maleimide reaction using only one type of photochemical reaction. Polymer post-functionalization and hydrogel building with subsequent multipatterning using different maleimide molecules in a temporal sequential manner indicate that this photocontrolled Michael addition reaction can modulate the specific chemical events in a sequence.
Department of Chemistry & Key Laboratory for Advanced Materials, East China University of Science and Technology, 130# Meilong Road, Shanghai, 200237 (China).
Zhenzhen
Z
Liu
Tao
T
Liu
Qiuning
Q
Lin
Chunyan
C
Bao
Linyong
L
Zhu
click chemistry; hydrogels; photochemistry; polymers; spiro compounds