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NLOphoric 3,6-di(substituted quinoxalin) Carbazoles – Synthesis, Photophysical Properties and DFT Studies

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Abstract

Synthesis of novel 3,6-di(substituted quinoxalin) carbazole fluorophores by the condensation of 1,1′-(9-ethyl-9H-carbazole-3,6-diyl)bis(2-bromoethanone) with methyl, chloro and unsubstituted o-phenylenediamine is presented. Synthesized derivatives are well characterized by 1H NMR, 13C NMR, FTIR and Mass spectroscopy. Photophysical studies are carried out using solvents of varying polarities revealed positive solvatochromism and intramolecular charge transfer from carbazole (Donor) to quinoxalin (Acceptor). Intramolecular charge transfer properties are correlated by dipole moment changes and different polarity functions like Lippert–Mataga, Bilot-Kawski, Bakhshiev and Liptay plots with very good regression factors. Mulliken hush-analysis further support charge transfer characteristic. Linear and Nonlinear optical properties are explained by solvatochromic data using two-level quantum mechanical model and are correlated with computational calculations using density functional theory at B3LYP/6-31G(d) level. First hyperpolarizability value of all the synthesized compounds is found to be greater than urea by >333 times. Moreover, increase of hyperpolarizability values from non-polar to polar solvents are in good correlation with the significant charge transfer characteristic in polar solvents.

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Acknowledgements

Rahul Telore is grateful to UGC-CAS for providing fellowship under SAP. Amol Jadhav is thankful to UGC for fellowship.

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Authors and Affiliations

  1. Department of Dyestuff Technology, Institute of Chemical Technology, Matunga, Mumbai, 400 019, India

    Rahul D. Telore, Amol G. Jadhav & Nagaiyan Sekar

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  1. Rahul D. Telore
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  2. Amol G. Jadhav
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  3. Nagaiyan Sekar
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Correspondence to Nagaiyan Sekar.

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Telore, R.D., Jadhav, A.G. & Sekar, N. NLOphoric 3,6-di(substituted quinoxalin) Carbazoles – Synthesis, Photophysical Properties and DFT Studies. J Fluoresc 27, 1531–1540 (2017). https://doi.org/10.1007/s10895-017-2092-4

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