2,3-di(2-furyl) quinoxaline bearing 3-ethyl rhodanine and 1,3 indandione based heteroaromatic conjugated T-shaped push -pull chromophores: Design, synthesis, photophysical and non-linear optical investigations

Gopi, Vidya and Subbiahraj, Saravanan and Chemmanghattu, Karthika and Ramamurthy, Praveen C (2020) 2,3-di(2-furyl) quinoxaline bearing 3-ethyl rhodanine and 1,3 indandione based heteroaromatic conjugated T-shaped push -pull chromophores: Design, synthesis, photophysical and non-linear optical investigations. In: DYES AND PIGMENTS, 173 .

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Abstract

The design, synthesis, computational, spectroscopic, and, the second and third order non-linear optical studies of a two new pi-deficient cross-conjugated T-shaped push-pull molecules (QFR and QFI) consisting of 3-ethyl rhodanine and 1,3 indandione substituted with heterocyclic quinoxaline ring were synthesized by Knoevenagel condensation reaction of the precursor dialdehydes with active dye molecules were described in detail. In the as synthesized molecule, the electron donating thiophene moiety acts as an efficient pi-bridge on either side to the quinoxaline core that permits good viability in fine-tuning the optical absorption spectrum with good solubility. The computational studies of these molecules show efficient intra molecular charge transfer (ICT) processes analyzed through their molecular orbital characteristics, excitation energy, absorption maxima, oscillator strength and Mulliken population analysis. The comparison study between the structures of these push-pull molecules were done by their photophysical characteristics including CIE coordinates; thermal characteristics, XRD studies and electrochemical analysis. The time-resolved fluorescence spectra with nanosecond time profile were measured to detect the delayed fluorescent performance of the push-pull molecules QFR and QFI. HyperRayleigh scattering (HRS) in chloroform solution of varying concentrations, using a standard wavelength at 1064 nm was used to assess their first order hyperpolarizability. Optical non-linear property was again proved by open-aperture Z-scan technique investigated at 532 nm and the observed optical limiting behavior was originated from the reverse saturable absorption (RSA) process. The second and third order NLO studies reveals that 3-ethyl rhodanine substituted QFR molecule (beta value from HRS, 84.64 x 10(-30) esu and beta(eff) from Z scan, 10 x 10(-10) m/W) shows high non-linear optical properties and thermal stability compared with 1,3 indandione substituted QFI (beta value from HRS, 48.00 x 10(-30) esu and beta(eff) value from Z scan, 2 x 10(-10)m/W).

Item Type:	Journal Article
Publication:	DYES AND PIGMENTS
Publisher:	ELSEVIER SCI LTD
Additional Information:	Copyright of this article belongs to ELSEVIER SCI LTD
Keywords:	Non-linear optics (NLO); Push-pull molecules; Rhodanine; Indandione; Hyper-Rayleigh scattering; Z-Scan analysis
Department/Centre:	Division of Chemical Sciences > Inorganic & Physical Chemistry Division of Mechanical Sciences > Materials Engineering (formerly Metallurgy)
Date Deposited:	13 Jan 2020 07:46
Last Modified:	13 Jan 2020 07:46
URI:	http://eprints.iisc.ac.in/id/eprint/64314

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