A Green Synthesis of 2‐Amino‐4‐(9<i>H</i>‐carbazole‐3‐yl)thiophene‐3‐carbonitriles by a Step‐wise and One‐pot Three‐component <scp>Gewald</scp> Reaction

Avula, Vijay Kumar Reddy; Vallela, Swetha; Anireddy, Jaya Shree; Chamarthi, Naga Raju

doi:10.1002/jhet.2847

Cited by 10 publications

(4 citation statements)

References 25 publications

(18 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The first step is acylation of N ‐ethyl carbazole by slightly modifying the reported procedure to give the precusor 3 , 1‐(9‐Ethyl‐9H‐carbazol‐3‐yl)ethan‐1‐one. This intermediates 3 on Knoevenagel condensation with malononitrile yields the intermediate 4 , 2‐(1‐(9‐Ethyl‐9H‐carbazol‐3‐yl)ethylidene)malononitrile in the subsequent step catalyzed by basic ammonium acetate . In the final step, intermediate 4 on condensation with commercially procured different aldehydes R a , R b , and R c gave the corresponding fluorophores 5 a , 5 b , and 5 c .…”

Section: Resultsmentioning

confidence: 99%

N‐Ethyl Carbazole Derived D‐π‐A‐π‐D Based Fluorophores: Consolidated Spectroscopic, Viscosity and DFT Studies

2019

View full text Add to dashboard Cite

This article reports design and synthesis of three new fluorophores (5 a‐c) with the donor‐π‐acceptor‐π‐donor motif, where dicyano vinylene group is the central acceptor, N‐ethyl carbazole group is a fixed donor and varying the N‐substituted secondary donors so as to study their photophysical behavior. Based on the systematic photophysical and theoretical reconnaissances, the fluorophores structure‐property relationships are defined. Their spectral and photophysical behaviors are affected by the solvent polarity, with a significant bathochromic shift in emission and large Stoke shifts being observed in polar solvents. Contrary to dipolar asymmetric analogue this system shows an efficient intramolecular charge transfer as observed from various solvent polarity plots. For 5 a, 5 b, and 5 c, the viscosity induced emission studies show respectively 3.78, 6.53, and 6.82 times enhancement in their fluorescence intensity and hence act as a fluorescent molecular rotor (FMR). The structure and electronic properties of these fluorophores were evaluated using density functional theory computations using B3LYP/6‐311++G(d,p). The frontier molecular orbitals and the optimized geometry reveal that secondary donors in each fluorophore donate the electron and not the N‐ethyl carbazole group which is more twisted. The non‐linear and linear optical properties were determined employing solvatochromic and computational methods in solvents of varying polarities with results falling within the expected limiting values. The linear and non‐linear optical properties of the fluorophores change with the strength of different secondary donors used and solvent polarity. The two photon absorption cross‐section described using two level approximation is highest for 5 b (115‐172 GM).

show abstract

Section: Resultsmentioning

confidence: 99%

N‐Ethyl Carbazole Derived D‐π‐A‐π‐D Based Fluorophores: Consolidated Spectroscopic, Viscosity and DFT Studies

2019

View full text Add to dashboard Cite

show abstract

“…The synthon, 3-acetyl-N-methyl-carbazole (1) was synthesized according to the earlier reports [21][22][23]. In order to achieve the target compounds, the one of the way is to convert keto group into quinoline by means of well-known Pfitzinger reaction [24], in which a carbazole linked quinoline compound was synthesized by one step method.…”

Section: Resultsmentioning

confidence: 99%

“…The mass spectra were taken on Agilent single quad mass spectrometer. Compound 3-acetyl-9-methyl-9H-carbazole (3Ac-Cbz, 1) was synthesized according to reported procedure [21][22][23]. Product purity was assessed through TLC plates coated with silica gel-G, employing a mixture of petroleum ether and ethyl acetate as mobile phase.…”

Section: Methodsmentioning

confidence: 99%

A Facile One Pot Synthesis and Anticorrosion Potential of Carbazole Linked Quinoline Moiety

Panneerselvi,

Muthukrishnan,

Shankar

et al. 2023

ajc

View full text Add to dashboard Cite

A facile and efficient one pot synthesis has been developed for the preparation of quinoline-substituted carbazoles 3-(4-carboxyquinolin-2-yl)-9-methyl-9H-carbazole (Cbz-QCA) and 3-(4-chloroquinolin-2-yl)-9-methyl-9H-carbazole (Cbz-ClQ) by treating 3-acetyl-9-methyl-9H-carbazole (3Ac-Cbz), with isatin under Pfitzinger reaction conditions and utilizing anthranilic acid in the presence of POCl3 through the modified Niementowski method, respectively. The synthesized compounds have been comprehensively characterized through spectral data. The effect of 3Ac-Cbz (1), Cbz-QCA (2) and Cbz-ClQ (3) were assessed as a steel corrosion inhibitor in molar hydrochloric acid using weight loss, potentiodynamic polarization, and electrochemical methods. The inhibitory effect rises with tested inhibitor concentration, reaching above 84% at higher concentrations of all tested inhibitors. These results indicated that tested inhibitors have a good corrosion inhibition. An increase in the inhibitor’s concentration leads to a higher percentage of inhibition efficiency, driven by the adsorption of inhibitor molecules onto the metal surface. Results from scanner electron microscopy (SEM) support the experimental inhibition tests have yielded successful outcomes and validate the adsorption process.

show abstract

“…The parent chromophore, 1‐(4‐(diphenylamino)phenyl)ethan‐1‐one ( 3 ) was synthesized by the acylation of triphenylamine by slightly modifying the procedure as described in the literature . The Knoevenagel condensation of 3 with malononitrile using a catalytic amount of ammonium acetate yielded 2‐(1‐(4‐(diphenylamino)phenyl)ethylidene)malononitrile ( 4 ) . Aldehydes R a , R b and R c were procured from the commercial sources.…”

Section: Methodsmentioning

confidence: 99%

NLOphoric Triphenylamine Derived Donor‐π‐Acceptor‐π‐Donor Based Colorants: Synthesis, Spectroscopic, Density Functional Theory and Z‐scan Studies

Raikwar

Mathew²,

Varghese³

et al. 2019

Photochem & Photobiology

View full text Add to dashboard Cite

Three Donor-p-Acceptor-p-Donor type styryl dyes (5a-c) with different secondary donors are synthesized and characterized to study their nonlinear and linear optical properties. The structure-property relationships of the dyes are described in the light of systematic photophysical and theoretical investigations. The photophysical characteristics of 5a-c are influenced by the polarity of the medium, with an appreciable bathochromic shift in emission (5b = 81 nm) and large Stoke shifts (5b = 104-173 nm) in polar solvents. 5a-c showed intramolecular charge transfer characteristics recognized with the help of emission solvatochromism, solvent polarity graphs, natural bond orbital analysis and HOMO-LUMO energy difference. The optimized geometry and frontier molecular orbitals reveal that the electron donation takes place from secondary donors and not from a fixed donor (triphenylamine) which is more twisted. The nonlinear optical properties obtained using solvent induced spectral shift and computational methods are found within the limiting values. Z-scan results reveal saturable kind of behavior for 5a, 5b and 5c, whereas 5a and 5b show reverse saturable kind of behavior in acetone and ethanol and hence give optical limiting values. The two-photon absorption cross section described by two-level approximation is highest for 5b (251-300 GM).

show abstract

A Green Synthesis of 2‐Amino‐4‐(9H‐carbazole‐3‐yl)thiophene‐3‐carbonitriles by a Step‐wise and One‐pot Three‐component Gewald Reaction

Cited by 10 publications

References 25 publications

N‐Ethyl Carbazole Derived D‐π‐A‐π‐D Based Fluorophores: Consolidated Spectroscopic, Viscosity and DFT Studies

N‐Ethyl Carbazole Derived D‐π‐A‐π‐D Based Fluorophores: Consolidated Spectroscopic, Viscosity and DFT Studies

A Facile One Pot Synthesis and Anticorrosion Potential of Carbazole Linked Quinoline Moiety

NLOphoric Triphenylamine Derived Donor‐π‐Acceptor‐π‐Donor Based Colorants: Synthesis, Spectroscopic, Density Functional Theory and Z‐scan Studies

Contact Info

Product

Resources

About