The effect of the additional phenyl moiety on the linear and quadratic nonlinear optical properties of chromophores with vinyl-quinoxalinone-vinyl π-bridge

• Published in: Journal of photochemistry and photobiology. A, Chemistry. Chemistry., 2022-10, Vol.431, p.114013, Article 114013
• Main Authors: Islamova, Liliya N., Kalinin, Alexey A., Gaysin, Adel I., Fazleeva, Guzel M., Shmelev, Artemiy G., Sharipova, Sirina M., Shalin, Nikita I., Mukhtarov, Anvar S., Vakhonina, Tatyana A., Fominykh, Olga D., Yu. Balakina, Marina
• Format: Article
• Language: English
• Subjects: NLO chromophore; NLO coefficient; Second Harmonic Generation; TD-DFT calculations; Vinylene-quinoxalinone-vinylene bridge
• ISSN: 1010-6030; 1873-2666
• DOI: 10.1016/j.jphotochem.2022.114013

[Display omitted] •Quinoxalinone-based chromophores with aniline/heteroaryl donors have been synthesized.•Experimental and theoretical absorption spectra of chromophores were compared.•First hyperpolarizability of chromophores was calculated at DFT level.•NLO coefficients of PMMA doped with the chromophores were measured by SHG techique. Four novel push-pull tricyanofuran-based chromophores with vinylene-quinoxalinone-vinylene π-conjugated bridge and aniline type donor with phenyl moiety either introduced into the donor/acceptor as substituent or fused with aniline in carbazole and phenothiazine structures have been synthesized and their linear and nonlinear optical properties were systematically investigated by UV–Vis spectroscopy and DFT calculations. Addition of benzene ring as substituent to the chromophore leads to moderate (22–36 pm/V) macroscopic NLO activity of composite chromophore/PMMA materials, while guest-host polymers doped with chromophores with fused heterocyclic donor moiety demonstrate higher d33 values up to 47 pm/V. Chromophore-containing polymer films preserve more than 90% of d33 after 1000 h at ambient temperature.