Elsevier, Journal of Luminescence, 6(130), p. 1085-1091
DOI: 10.1016/j.jlumin.2010.01.029
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Biphenyl derivative N-allyl-N′-(4′-nitro[1,1′-biphenyl]-4-yl)thiourea (BP1) was synthesized as a functional fluorescent sensor for protons and their photophysical properties were studied. The influence of environment protonation on photophysical properties of the biphenyls in solutions was investigated using UV absorption, steady-state and time-resolved fluorescence spectroscopy. Semi-empirical and DFT calculations and optimization of the molecular structure of the biphenyl derivatives in vacuum, in polar solvents and in a proton-rich environment were conducted using the HyperChem, Amsol and Gaussian3 software package. Fluorescence quenching with addition of acidic acid was observed and the Stern–Volmer quenching rate constant was about 3.0×109 M−1 s−1. Intermolecular hydrogen bonds formations by the protons with the sulphur being substituted to the biphenyls generate charge movement and strong increase (×5) of the dipole moment of the fluorophore.