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Solvent Effects on the Photophysical Properties of Unexplored Imidazo[1,2‑a]pyridine Derivatives
Victor H Justino Garcia Praciano1, Luan A Martinho1, Guilherme Duarte Ramos Matos2
1Instituto de Química, Laboratório de Química Metodológica e Orgânica Sintética (LaQMOS), Universidade de Brasília, Campus Universitário Asa Norte, Brasília, DF 70904-970, Brazil.
Abstract:
Simple imidazo-[1,2-a]-pyridine derivatives were synthesized via the GBB reaction, and their photophysical properties were studied for the first time. Fluorescence quantum yields confirmed a push-pull design, and absorption spectra showed a blue shift for bromo- and nitro-substituted derivatives at the ortho position (4b, 4d), whereas the cyano-substituted analogs at the para position (4f, 4p) exhibited a red shift. Solvent polarity significantly affected the fluorescence spectra, causing a red shift in polar solvents (4p, 4r) and a blue shift in nonpolar solvents (4i, 4m). A significant Stokes shift supported the involvement of an ICT mechanism in most cases. Some of the compounds demonstrated promising properties for use in fluorescent materials.
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