A novel NIR violanthrone derivative with high electron-deficiency: effect of fluorescence on dicyanomethylene substitution |
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Authors: | Bo Liu Duo Fan Qiong Zhang Yu Chen Weihong Zhu |
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Institution: | (1) Department of Chemistry, Jahangirnagar University, Savar, Dhaka, 1342, Bangladesh;(2) Department of Chemistry, University of Waikato, Hamilton, New Zealand;(3) Department of Chemistry, The University of Montana, Missoula, Montana 59812, USA; |
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Abstract: | Near infrared (NIR) dyes attracted increasing interests in widely potential applications, such as fluorescent probe and living
organism imaging, due to their low background signals from biomolecules, low light scattering and deep penetration, and low-cost
excitation light sources. A novel NIR violanthrone derivative (VA-CN) with dicyanomethylene substitution was synthesized and
fully characterized by 1H NMR, 13C NMR, HRMS, and IR spectrometry. It is demonstrated that the original planar conformation of violanthrone ring (the nine
fused benzene rings) becomes twisted and unsymmetrical upon the incorporation of two strong electron-withdrawing dicyanomethylene
units. Photophysical, electrochemical performances as well as distinct solvatochromic effects were studied in detail. Considering
the low reduction potential (−0.56 V vs NHE), VA-CN could be considered as a good electron acceptor due to the strong electron
deficiency resulted from dicyanomethylene group. A distinct increase in fluorescence was observed with 30-fold enhancement
upon the addition of n-butyl amine. The reversible fluorescence “off-on” shows that VA-CN might be served as a promising fluorescent sensor for electron-rich amines. |
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