期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 83, 期 7, 页码 3669-3678出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.8b00033
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资金
- Department of Atomic Energy (DAE-SRC) [21/13/2015-BRNS/35029]
- UGC
- DST
- CSIR, New Delhi, India
A facile synthesis and detailed photophysical investigation of E/Z-isomerization of fluorescent diphenylamine tethered stilbene derivatives (DPASs) under white light exposure have been carried out to understand the effect on fluorescence, electrochemical properties, and photostability under various activation/deactivation pathways. In solution state, in the dark, the E-isomer of DPASs (6a-d) exhibited high fluorescence quantum yields (Phi(fl) approximate to 53% to 60% in DMSO). However, on white light exposure, H-1 NMR and HPLC studies revealed that pure E-isomer of the DPAS 6a (similar to 9.5 mM) started converting into its Z-form by photo-isomerization until it reaches to nearly equilibrium. At low concentrations (similar to 10 mu M), the absorption band of the pure E-isomer in the range of 350-450 nm gradually decreased to adopt Z-conformation 6a' until a photostationary state was reached. The structure of the E-isomer 6a was unequivocally confirmed by X-ray diffraction analysis. The synthesized DPAS compounds 6a-d possessed positive solvatochromic properties, two photon absorption properties, and good thermal stability. The electrochemical investigations using DPASs showed reversible oxidation resulting in formation of a stable radical cation. Owing to useful photophysical, electrochemical and thermal properties, these DPAS derivatives are suitable for their application in biomedical imaging as well as in fabrication of electroluminescent materials.
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