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Et₃N/DMSO-supported one-pot synthesis of highly fluorescent β-carboline-linked benzothiophenones via sulfur insertion and estimation of the photophysical properties.

ABSTRACT: A robust transition-metal-free strategy is presented to access novel β-carboline-tethered benzothiophenone derivatives from 1(3)-formyl-β-carbolines using elemental sulfur activated by Et₃N/DMSO. This expeditious catalyst-free reaction proceeds through the formation of β-carboline-based 2-nitrochalcones followed by an incorporation of sulfur to generate multifunctional β-carboline-linked benzothiophenones in good to excellent yields. The synthetic strategy could also be extended towards the synthesis of β-carboline-linked benzothiophenes. Moreover, the afforded products emerged as promising fluorophores and displayed excellent light-emitting properties with quantum yields (Φ_F) up to 47%.

SUBMITTER: Singh D

PROVIDER: S-EPMC7385337 | biostudies-literature | 2020

REPOSITORIES: biostudies-literature

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Et<sub>3</sub>N/DMSO-supported one-pot synthesis of highly fluorescent β-carboline-linked benzothiophenones via sulfur insertion and estimation of the photophysical properties.

Singh Dharmender D Kumar Vipin V Singh Virender V

Beilstein journal of organic chemistry 20200720

A robust transition-metal-free strategy is presented to access novel β-carboline-tethered benzothiophenone derivatives from 1(3)-formyl-β-carbolines using elemental sulfur activated by Et<sub>3</sub>N/DMSO. This expeditious catalyst-free reaction proceeds through the formation of β-carboline-based 2-nitrochalcones followed by an incorporation of sulfur to generate multifunctional β-carboline-linked benzothiophenones in good to excellent yields. The synthetic strategy could also be extended towar ...[more]

PMID: 32765794

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Project description:The donor-acceptor-π-conjugated (D-π-)2A fluorescent dyes OUY-2, OUK-2 and OUJ-2 with two (diphenylamino)carbazole thiophene units as D (electron-donating group)-π (π-conjugated bridge) moiety and a pyridine, pyrazine or triazine ring as electron-withdrawing group (electron-accepting group, A) have been designed and synthesized. The photophysical and electrochemical properties of the three dyes were investigated by photoabsorption and fluorescence spectroscopy, Lippert-Mataga plots, cyclic voltammetry and density functional theory calculations. The photoabsorption maximum (λmax,abs) and the fluorescence maximum (λmax,fl) for the intramolecular charge-transfer characteristic band of the (D-π-)2A fluorescent dyes show bathochromic shifts in the order of OUY-2 < OUK-2 < OUJ-2. Moreover, the photoabsorption bands of the (D-π-)2A fluorescent dyes are nearly independent of solvent polarity, while the fluorescence bands showed bathochromic shifts with increasing solvent polarity (i.e., positive fluorescence solvatochromism). The Lippert-Mataga plots for OUY-2, OUK-2 and OUJ-2 indicate that the Δμ (= μe - μg) value, which is the difference in the dipole moment of the dye between the excited (μe) and the ground (μg) states, increases in the order of OUY-2 < OUK-2 < OUJ-2. Therefore, the fact explains our findings that OUJ-2 shows large bathochromic shifts of the fluorescence maxima in polar solvents, as well as the Stokes shift values of OUJ-2 in polar solvents are much larger than those in nonpolar solvents. The cyclic voltammetry of OUY-2, OUK-2 and OUJ-2 demonstrated that there is little difference in the HOMO energy level among the three dyes, but the LUMO energy levels decrease in the order of OUY-2 > OUK-2 > OUJ-2. Consequently, this work reveals that for the (D-π-)2A fluorescent dyes OUY-2, OUK-2 and OUJ-2 the bathochromic shifts of λmax,abs and λmax,fl and the lowering of the LUMO energy level are dependent on the electron-withdrawing ability of the azine ring, which increases in the order of OUY-2 < OUK-2 < OUJ-2.

Dataset Information

Et₃N/DMSO-supported one-pot synthesis of highly fluorescent β-carboline-linked benzothiophenones via sulfur insertion and estimation of the photophysical properties.

Publications

Et<sub>3</sub>N/DMSO-supported one-pot synthesis of highly fluorescent β-carboline-linked benzothiophenones via sulfur insertion and estimation of the photophysical properties.

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Et3N/DMSO-supported one-pot synthesis of highly fluorescent β-carboline-linked benzothiophenones via sulfur insertion and estimation of the photophysical properties.

Publications

Et<sub>3</sub>N/DMSO-supported one-pot synthesis of highly fluorescent β-carboline-linked benzothiophenones via sulfur insertion and estimation of the photophysical properties.

Similar Datasets

OmicsDI is part of the ELIXIR infrastructure

Tweets

Et₃N/DMSO-supported one-pot synthesis of highly fluorescent β-carboline-linked benzothiophenones via sulfur insertion and estimation of the photophysical properties.