title: Unparalleled Ease of Access to a Library of Biheteroaryl Fluorophores via Oxidative Cross-Coupling Reactions: Discovery of Photostable NIR Probe for Mitochondria.
abstract: The development of straightforward accesses to organic functional materials through C-H activation is a revolutionary trend in organic synthesis. In this article, we propose a concise strategy to construct a large library of donor-acceptor-type biheteroaryl fluorophores via the palladium-catalyzed oxidative C-H/C-H cross-coupling of electron-deficient 2H-indazoles with electron-rich heteroarenes. The directly coupled biheteroaryl fluorophores, named Indazo-Fluors, exhibit continuously tunable full-color emissions with quantum yields up to 93% and large Stokes shifts up to 8705 cm(-1) in CH2Cl2. By further fine-tuning of the substituent on the core skeleton, Indazo-Fluor 3l (FW = 274; λem = 725 nm) is obtained as the lowest molecular weight near-infrared (NIR) fluorophore with emission wavelength over 720 nm in the solid state. The NIR dye 5h specifically lights up mitochondria in living cells with bright red luminescence. Typically, commercially available mitochondria trackers suffer from poor photostability. Indazo-Fluor 5h exhibits superior photostability and very low cytotoxicity, which would be a prominent reagent for in vivo mitochondria imaging.
authors: Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, and State Key Laboratory of Biotherapy, West China Hospital, West China Medical School, Sichuan University , 29 Wangjiang Road, Chengdu 610064, China.
authors: Yangyang
authors: Y
authors: Cheng
authors: National Engineering Research Center for Biomaterials, Sichuan University , 29 Wangjiang Road, Chengdu 610064, China.
authors: Gaocan
authors: G
authors: Li
authors: Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, and State Key Laboratory of Biotherapy, West China Hospital, West China Medical School, Sichuan University , 29 Wangjiang Road, Chengdu 610064, China.
authors: Yang
authors: Y
authors: Liu
authors: Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, and State Key Laboratory of Biotherapy, West China Hospital, West China Medical School, Sichuan University , 29 Wangjiang Road, Chengdu 610064, China.
authors: Yang
authors: Y
authors: Shi
authors: Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, and State Key Laboratory of Biotherapy, West China Hospital, West China Medical School, Sichuan University , 29 Wangjiang Road, Chengdu 610064, China.
authors: Ge
authors: G
authors: Gao
authors: Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, and State Key Laboratory of Biotherapy, West China Hospital, West China Medical School, Sichuan University , 29 Wangjiang Road, Chengdu 610064, China.
authors: Di
authors: D
authors: Wu
authors: Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, and State Key Laboratory of Biotherapy, West China Hospital, West China Medical School, Sichuan University , 29 Wangjiang Road, Chengdu 610064, China.
authors: Jingbo
authors: J
authors: Lan
authors: Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, and State Key Laboratory of Biotherapy, West China Hospital, West China Medical School, Sichuan University , 29 Wangjiang Road, Chengdu 610064, China.
authors: Jingsong
authors: J
authors: You
mesh_terms: D005456:Fluorescent Dyes / Q000138:chemical synthesis / Q000737:chemistry*; D056945:Hep G2 Cells; D006801:Humans; D007191:Indazoles / Q000138:chemical synthesis / Q000737:chemistry*; D008163:Luminescent Measurements / Q000379:methods; D018613:Microscopy, Confocal; D008930:Mitochondria, Liver / Q000737:chemistry*; D010084:Oxidation-Reduction; D013876:Thiophenes / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D005456:Fluorescent Dyes; D007191:Indazoles; D013876:Thiophenes