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Spectroscopic Investigation and Photophysics of a D-π-A-π-D Type Styryl Pyrazine Derivative

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Abstract

E,E-2,5-bis(3,4-dimethoxystyryl)pyrazine (BDSP) has been prepared by aldol condensation between 2,5-dimethypyrazine and 3,4-dimthoxybenzaldehyde and characterized by IR, 1H NMR, 13C NMR and X-ray crystallography. The electronic absorption and emission properties of BDSP were studied in different solvents. BDSP displays a strong solvatochromic effect of the emission spectrum that is reflected by large red shifts of its fluorescence emission maximum on increasing the solvent polarity, indicating a large change in dipole moment of BDSP upon excitation due to photoinduced intramolecular charge transfer (PICT). Excited state intermolecular hydrogen bonding affects the energy of emission spectrum and fluorescence quantum yield of BDSP dye. The dye solutions (1 × 10−4 M) in DMSO, DMF, CH3CN and dioxane give laser emission in green region upon excitation by a 337.1 nm nitrogen pulse (λ = 337 nm). The tuning range, gain coefficient (α), emission cross – section (σe) and half-life energy (E1/2) has been determined. Ground and electronic excited states geometric optimization were performed using density functional theory (DFT) and time-dependent density functional theory (TD-DFT), respectively. A DFT natural bond analysis complemented the ICT. BDSP dye displays fluorescence quenching by colloidal silver nanoparticles (AgNPs). The fluorescence data reveal that radiative and non-radiative energy transfer play a major role in the fluorescence quenching mechanism.

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Acknowledgments

This work was supported by the Deanship of Scientific Research (DSR), King Abdulaziz University, Jeddah, under No (130–685-D1435). The authors, therefore, gratefully acknowledge the DSR technical and financial support.

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  1. Department of Chemistry, Faculty of Science, King Abdulaziz University, P.O. Box 80203, Jeddah, Saudi Arabia, 21589

    Samy A. El-Daly & Khalid A. Alamry

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El-Daly, S.A., Alamry, K.A. Spectroscopic Investigation and Photophysics of a D-π-A-π-D Type Styryl Pyrazine Derivative. J Fluoresc 26, 163–176 (2016). https://doi.org/10.1007/s10895-015-1698-7

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