A1 Journal article (refereed)
Nonlinear optical properties of diaromatic stilbene, butadiene and thiophene derivatives (2021)

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

JYU authors or editors

Publication details

All authors or editors: Kukkonen, Esa; Lahtinen, Elmeri; Myllyperkiö, Pasi; Haukka, Matti; Konu, Jari

Journal or series: New Journal of Chemistry

ISSN: 1144-0546

eISSN: 1369-9261

Publication year: 2021

Volume: 15

Issue number: 45

Pages range: 6640-6650

Publisher: Royal Society of Chemistry (RSC)

Publication country: United Kingdom

Publication language: English

DOI: https://doi.org/10.1039/d1nj00456e

Publication open access: Openly available

Publication channel open access: Partially open access channel

Publication is parallel published (JYX): https://jyx.jyu.fi/handle/123456789/74913

Abstract

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.

Keywords: organic compounds; aromatic compounds; stilbenes; butadiene; crystals; optical properties

Contributing organizations

Ministry reporting: Yes

VIRTA submission year: 2021

JUFO rating: 1