Synthesis, crystal structure and spectral characteristics of highly fluorescent chalcone-based coumarin in solution and in polymer matrix

• New fluorescent chalcone based-coumarin was synthesized by Claisen Schmidt method.
• Crystal structure was investigated by single crystal X-ray diffraction at T=120 K.
• We report the photoluminescent behaviors of coumarin chalcone doped in PMMA films.
• One emission band centered at 516 nm.
• Coumarin-based chromophores could be potential optical materials.

A new coumarin chalcone 3-((2E)-3-(2-hydroxyphenyl) prop-2-enoyl)-4-hydroxy-2(H)-chromen-2-one was synthesized using the Claisen Schmidt reaction by the condensation of 3-acetyl-4-hydroxycoumarin and 2-hydroxybenzaldehyde using a mild organic base. This novel compound was characterized by 1H NMR, FT-IR and UV–vis spectroscopy. Single crystal X-ray diffraction investigation at low temperature (T=120 K) shows that this compound exhibits an intramolecular O3–H…O hydrogen bond, the coumarin ring and the phenyl group are nearly coplanar and the crystal packing is stabilized by intermolecular O3–H…O contacts and π–π stacking interactions. This ortho-hydroxyphenyl-4-hydroxycoumarin chalcone exhibits a strong blue-green emission under visible light excitation at 470 nm. The fluorescence behaviors of this compound doped in poly(methyl methacrylate) (PMMA) were investigated.

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