Nonlinear optical properties of diaromatic stilbene, butadiene and thiophene derivatives
Kukkonen, E., Lahtinen, E., Myllyperkiö, P., Haukka, M., & Konu, J. (2021). Nonlinear optical properties of diaromatic stilbene, butadiene and thiophene derivatives. New Journal of Chemistry, 15(45), 6640-6650. https://doi.org/10.1039/d1nj00456e
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New Journal of ChemistryDate
2021Discipline
Epäorgaaninen kemiaEpäorgaaninen ja analyyttinen kemiaNanoscience CenterFysikaalinen kemiaInorganic ChemistryInorganic and Analytical ChemistryNanoscience CenterPhysical ChemistryCopyright
© The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2021
Series of highly polar stilbene (1a–e), diphenylbutadiene (2a–c) and phenylethenylthiophene (3a–c) derivatives were prepared via Horner–Wadsworth–Emmons method with a view to produce new and efficient materials for second harmonic generation (SHG) in the solid-state. The single-crystal X-ray structures of compounds 1–3 reveal extensive polymorphism and a peculiar photodimerization of the 2-chloro-3,4-dimethoxy-4′-nitrostilbene derivative 1a to afford two polymorphs of tetra-aryl cyclobutane 4. The stilbene congeners 2-chloro-3,4-dimethoxy-4′-nitrostilbene (1a·non-centro), 5-bromo-2-hydroxy-3-nitro-4′-nitrostilbene (1b) and 4-dimethylamino-4′-nitrostilbene (1e), as well as 4′-fluoro-4′′-nitro-1,4-diphenyl-1,3-butadiene (2a) present the ideal, non-centrosymmetric arrangement of the chromophores for nonlinear optical (NLO) activity. Compounds 1b and 2a exhibit only relatively low intensity for second harmonic generation (0.04 and 0.18 times that of urea reference, respectively), while the stilbene polymorph 1a·non-centro shows NLO activity of over 32 times that of urea. In addition, the conjugated diaromatic compounds 1–3 display fluorescence behaviour in CH2Cl2 solutions with the exception of stilbene derivative 1b.
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The authors gratefully acknowledge financial support from the Finnish Cultural Foundation and the Magnus Ehrnrooth Foundation.License
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