We have designed and synthesized a carbazole-based fluorescent probe (CZ-Nm) for the specific recognition of GSH over Cys and Hcy. The probe is almost non-fluorescent owing to the photoinduced electron transfer (PET) process from the carbazole fluorophore to the nitroolefin moiety. Upon treatment with GSH, owing to the Michael addition of GSH to the double bond of the nitroolefin moiety, the probe shows a fluorescence enhancement and absorption change. The CZ-Nm probe displays desirable properties such as acting as a “naked eye” probe, a wide linear range of 0–0.01 M, high sensitivity, and strong anti-jamming capability. More importantly, the probe can also be successfully applied to the detection of intracellular GSH with a bright fluorescence signal, good cell permeability and bio-compatibility.
Tianzhi Yu,Yan Cao,Wenming Su,Chengcheng Zhang,Yuling Zhao,Duowang Fan,Mingjun Huang,Kan Yue,Stephen Z. D. Cheng
A new iridium complex containing coumarin derivative as a cyclometalated ligand (1L) and a carbazole-functionalized β-diketonate (2L) as the ancillary ligand, namely, Ir(III)bis(3-(pyridin-2-yl)coumarinato-N,C4)(1-(9-butyl-9H-carbazol-3-yl)-4,4,4-trifluoro-butane-1,3-dionato-O,O) (Ir(1L)2(2L)), was synthesized. The crystal structure of Ir(1L)2(2L) was determined via combined wide angle X-ray diffraction (WAXD) and transmission electron microscopy (TEM), which showed π–π the interactions of Ir(1L)2(2L) molecules stacking along the crystal axes. The doped light-emitting diodes using this novel Ir(1L)2(2L) complex as the phosphorescent dopant were fabricated. At a Ir(1L)2(2L) concentration of 6.0 wt%, a green-yellow emitting OLED was achieved with a maximum external quantum efficiency (EQE) of 6.11% and a maximum luminous efficiency of 22.55 cd A−1 at the current density of 6.06 mA cm−2, and a maximum luminance of 6653 cd m−2 at 10.7 V. Furthermore, two reference complexes Ir(1L)2(acac) and Ir(1L)2(TTA) were also used as emitters to fabricate OLED devices with the same device configuration. The maximum luminous efficiency of Ir(1L)2(acac) doped device was measured to be 20.04 cd A−1 at 2.15 mA cm−2 (10.0 wt%), while the doped device of Ir(1L)2(TTA) had a maximum luminous efficiency of 16.59 cd A−1 at 1.36 mA cm−2. The better performances of Ir(1L)2(2L) doped devices could be largely attributed to an improved hole-transporting property due to the introduction of the carbazole moiety.
Meng-qiu Song,Wei Min,Jing Wang,Xin-Xin Si,Xiu-Jun Wang,Yu-Wei Liu,Da-Hua Shi
Twelve carbazole-coumarin hybrids were synthesized and biologically evaluated as dual binding site acetylcholinesterase inhibitors. The structures of the carbazole-coumarin hybrids were confirmed by IR, NMR, HRMS and single-crystal X-ray diffraction studies. The compound 3j had the crystal system of triclinic and the space group of P-1. The cholinesterase inhibitory activity of synthesized compounds was measured using colorimetric Ellman's method. Compound 3h exhibited good acetylcholinesterase (AChE) inhibitory activity (IC 50 value of 6.72 μ M) and a high selectivity over butyrylcholinesterase (BuChE). Compound 3k showed the best BuChE inhibitory activity with the IC 50 of 0.50 μM. The SAR studies revealed that the linker length played a crucial role in determining AChE inhibitory activity and the structure of the coumarin moieties affected the BuChE-inhibition activities of the hybrids. Molecular docking study of compound 3h indicated that it interacts with the crucial amino acids present at the catalytic active site and peripheral anionic site of AChE. Compound 3h would be a promising drug candidate to treat AD as a selective and dual binding site inhibitor of AChE.
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