Fluorescent Styryl Dyes Based on Novel 4-Methoxy-9-Methyi-9H-Carbazole-3-Carbaldehyde—Synthesis, Photophysical Properties and DFT Computations

Umape, Prashant G.; Gawale, Yogesh; Sekar, Nagaiyan

doi:10.1007/s10895-014-1389-9

Cited by 5 publications

(4 citation statements)

References 45 publications

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“…Це показує, наскільки пліднішими можуть бути відновлювальні трансформації молекули, зображеної на рис. 1, у випадку, коли окрім акрилонітрильного фрагменту до відновлення здатні також групи у складі замісників R 1 -R 3 . Власне у структурі естеру {1-[2-(4-нітрофеніл)-2-ціановініл]фенокси}оцтової кислоти (рис.…”

Section: рис 1 загальна формула 3-(2-алкоксифеніл)-2-(гет)арилакрилunclassified

“…Останнім часом 3-(2-алкоксифеніл)-2-(гет)арилакрилонітрили (рис. 1) знайшли практичне застосування в різних сферах: від розробки нових лікарських засобів [1,2] до оптики [1,3,4], у тому числі -галузі полімерних LEDматеріалів [5]; є відомості про дієві флуоресцентні зонди [6,7] та спроби створити хемосенсори [8] на основі подібних речовин. Такий широкий набір корисних властивостей обумовлено специфічною комбінацією близько розташованих у просторі функціональних груп, а унікальність кожної молекули забезпечується різною природою ароматичних та гетероароматичних систем (R 1 , рис.…”

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Methyl Ester of {2-[2-Cyano-2-(4-Nitrophenyl)vinyl]phenoxy}acetic Acid in Reduction Processes

Kuziv

Shablykina

Khilya

2017

Bull. T. Shevchenko Nat. Univ. Kyiv. Chem.

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3-(Het)aryl-3-(2-alkoxyphenyl)acrylonitriles are very practical polyfunctional molecules for organic synthesis; in particular difficult objects with near placed active groups can be easy obtained by the reduction of 3-(het)aryl-3-(2-alkoxyphenyl)acrylonitriles fragments. But now only reduction of activated C=C bond in such molecules mostly investigated. Previously it was shown by us that the action of sodium borohydride on esters of {2-[2-cyano-2-(4-nitrophenyl)vinyl]phenoxy}acetic acid caused not only saturation of C=C bond but also reduction of ester group to alcohol. So the results of reduction of 3-(het)aryl-3-(2-alkoxyphenyl)acrylonitriles can be more interest when other electrophilic fragment presents in molecule. And the aim of current work is the investigation of methyl ester of {2-[2-cyano-2-(4-nitrophenyl)vinyl]phenoxy}acetic acid behaviour in different reductive medium. Because of the very high electrophylity of observed molecule it's unfeasible to obtain good result in reactions with strong nucleophyles or with chemical reduction agents; that's why the hydrogenation in mild condition was used on the first step. It was found that the nitro group and the activated C=C bond were reducted simultaneously by H2 at 1.2 atm presure and room temperature with Pd/C catalizing; so methyl ester of {2-[2-(4-aminophenyl)-2-cyanoethyl]phenoxy}acetic acid was formed. Further hydrogenation took place on higher H2 presure (80 atm); and as a result of the saturation of C≡N bond methyl ester of {2-[3-amino-2-(4-aminophenyl)propyl]phenoxy}acetic acid creation occurred. The last compound can be transformed into 2-{2-[3-amino-2-(4-aminophenyl)propyl]phenoxy}ethanol by the LiAlH4 action. Such interesting structure also can be synthetized through the reduction of 3-[2-(2-hydroxyethoxy)phenyl]-2-(4-nitrophenyl)propionitrile that was obtained earlier: in the first step hydrogenation (1.2 atm H2) produced 3-[2-(2-hydroxyethoxy)phenyl]-2-(4-aminophenyl)propionitrile which nitrile group was reducted by LiAlH4 in the second step.

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Section: рис 1 загальна формула 3-(2-алкоксифеніл)-2-(гет)арилакрилunclassified

unclassified

Methyl Ester of {2-[2-Cyano-2-(4-Nitrophenyl)vinyl]phenoxy}acetic Acid in Reduction Processes

Kuziv

Shablykina

Khilya

2017

Bull. T. Shevchenko Nat. Univ. Kyiv. Chem.

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“…[73,74] Design and synthesis of push-pull systems consisting of carbazole unit as D and dicyano vinylene as A to achieve enhanced NLO properties are of contemporary interest. [75][76][77][78][79] This fact prompted us to take up this study so as to understand the effect of such variation on their NLO properties.…”

Section: Introductionmentioning

confidence: 99%

“…The systems with D‐π‐A‐π‐D architect have several advantages like improved non‐linearity, noncentrosymmetry and have better phase‐matching because of their larger off‐diagonal component as compared to the dipolar (D‐π‐A) systems . Design and synthesis of push‐pull systems consisting of carbazole unit as D and dicyano vinylene as A to achieve enhanced NLO properties are of contemporary interest . This fact prompted us to take up this study so as to understand the effect of such variation on their NLO properties.…”

Section: Introductionmentioning

confidence: 99%

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

2019

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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).

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Synthesis of Novel Carbazole based Styryl: Rational Approach for Photophysical Properties and TD-DFT

et al. 2014

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The synthesis and solvatochromic behavior of four novel carbazole based fluorescent styryl dyes were explained. In chlorinated solvents such as DCM and chloroform, these dyes show bathochromic shift in their absorption as well as emission. The styryl dyes 6b and 6c show solid state yellow fluorescence. DFT and TD-DFT computations were performed to study structural, molecular, electronic and photophysical properties of these dyes. The computed absorption and emission wavelength values are found to be in good agreement with the experimental results. The photophysical properties of these 1-styryl carbazole dyes are also compared with the recently reported 3-styrl carbazole dyes. The unique behavior of dye 6d is well explained by its optimized geometry found in the excited state. Ratio of ground to excited state dipole moment of the synthesized novel styryl compounds were calculated by Bakhshiev and Bilot-Kawski correlations.

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Fluorescent Styryl Dyes Based on Novel 4-Methoxy-9-Methyi-9H-Carbazole-3-Carbaldehyde—Synthesis, Photophysical Properties and DFT Computations

Cited by 5 publications

References 45 publications

Methyl Ester of {2-[2-Cyano-2-(4-Nitrophenyl)vinyl]phenoxy}acetic Acid in Reduction Processes

Methyl Ester of {2-[2-Cyano-2-(4-Nitrophenyl)vinyl]phenoxy}acetic Acid in Reduction Processes

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

Synthesis of Novel Carbazole based Styryl: Rational Approach for Photophysical Properties and TD-DFT

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