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Direct Olefination of Fluorinated Quinoxalines via Cross‐ Dehydrogenative Coupling Reactions: A New Near‐Infrared Probe for Mitochondria
Author(s) -
Zhang Zeyuan,
Zheng Yiwen,
Sun Zuobang,
Dai Zhen,
Tang Ziqiang,
Ma Jiangshan,
Ma Chen
Publication year - 2017
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201700237
Subject(s) - chemistry , quinoxaline , dichloromethane , photochemistry , fluorescence , infrared , palladium , catalysis , organic chemistry , physics , quantum mechanics , solvent , optics
Abstract A large library of 5,8‐distyrylquinoxaline fluorophores was synthesized in good‐to‐excellent yields via a palladium‐catalyzed oxidative C–H/C–H cross‐coupling of electron‐deficient fluorinated quinoxalines with electron‐rich styrenes. The resulting quinoxaline fluorophores (Qu‐Fluors) exhibited tunable color emissions with the quantum yields of up to 83% and large Stokes shifts of up to 6236 cm −1 in dichloromethane. The bioimaging performance of the Qu‐Fluors was shown to have potential as near‐infrared fluorescent probes for mitochondria.