Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 77, Issue 7, Pages 3475-3482Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo3002722
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Funding
- National Natural Science Foundation of China [61178061, 20903110]
- National High Technology Research and Development Program of China (863 Program) [2011AA03A110]
- Beijing Natural Science Foundation [2111002]
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Two series of new tetracyclic pyrazolo[3,4-b]pyridine-based coumarin chromophores were synthesized through a facile reaction between 3-aldehyde-7-diethylamino-coumarin (5) or 3-acetyl-7-diethylaminocoumarin (6) and 5-aminopyrazole derivatives (7) in a one-pot procedure. Different condensed products were obtained from compounds 5 and 6, and the potential reaction mechanism was studied using the reaction of 5 with 5-amino-1-phenylpyrazole (7a). The molecular structures were characterized by NMR and HAMS and confirmed by X-ray diffraction. The photophysical, electrochemical, and thermal properties of these compounds were investigated by absorption spectroscopy, fluorescence spectroscopy, single photon counting technique, cyclic voltammetry, thermogravimetric analysis, etc. Results show that the compounds exhibited high fluorescence quantum yields and good electrochemical, thermal, and photochemical stabilities. In addition, the application of these highly fluorescent compounds in living cell imaging was also explored by laser scanning confocal microscopy.
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