Coumarin‐Rhodamine Hybrids – Synthesis, Photophysical Properties, NLO Properties and DFT Studies

Shreykar, Milind R.; Sekar, Nagaiyan

doi:10.1002/slct.201601879

Cited by 14 publications

(19 citation statements)

References 79 publications

(157 reference statements)

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“…The onsagar radii (a 0 ), dipole moment (μ 0 ), mean polarizability (α 0 ), polarizability anisotropy (Δα 0 ), static first hyperpolarizability (β 0 ) and second hyperpolarizability ( γ 0 ) for the dyes 2 a‐e were calculated using BHandHLYP/6‐311++G(d,p) and CAM−B3LYP/6‐311++G(d,p) on the basis of finite field approach, and are summarized in Table S11. The detailed theory used for calculating theoretical and experimental values for NLO properties are provided in our previous reports …”

Section: Resultsmentioning

confidence: 99%

Tuning ‘Stokes Shift’ and ICT Character by Varying the Donor Group in Imidazo[1,5 a]pyridines: A Combined Optical, DFT, TD‐DFT and NLO Approach

Mohbiya

Sekar

2018

ChemistrySelect

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Imidazo [1, 5a]pyridine based novel donor-acceptor dyes (2a-e) with the large Stokes shift (ca. 140-200 nm) were synthesized and characterized. We report on the steady-state and nanosecond time-resolved emission studies of 2a-e in different microenvironments which reveal that the dyes 2a-c (average lifetime of 0.65, 1.36 and 1.63 ns respectively) perform reversible proton motion in chloroform due to variable donor group present at the para position of substituted phenyl group attached to imidazopyridine core as an acceptor group whereas 2d and 2e (average lifetime of 3.50 and 4.06 ns respectively) compete with 2a-c in agreement with considerable intramolecular charge transfer (ICT) characteristics. Solvent polarity plots viz. Lippert-Mataga, McRae, and Bakhshiev equation furnish the confirmation of ICT character. Density functional theory (DFT) calculations [(B3LYP/6-311 + +G(d, p)] provide the information of structural as well as the electronic properties of dyes 2a-e. Natural bond orbital (NBO) analyses enlighten the nature of the charge or proton transfer within the selected donor-acceptor orbital interaction with the large energy of stabilization (the donor-acceptor orbital interactions increases in the order 2a > 2b > 2c > 2d > 2e). The large difference in dipole moment (ca. 1.57-21.55 D) results in a strong non-linear optical (NLO) properties. The NLO properties were evaluated theoretically as well as spectroscopically in solvents of different polarities and the resulting hyperpolarizabilities fall within the expected limiting values. These results bring new findings in coupled ICT and proton transfer reactions which will be useful for further research and promising applications in sensing polarity or H-bonding of microenvironments similar to that of the biological ones.

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Section: Resultsmentioning

confidence: 99%

Tuning ‘Stokes Shift’ and ICT Character by Varying the Donor Group in Imidazo[1,5 a]pyridines: A Combined Optical, DFT, TD‐DFT and NLO Approach

Mohbiya

Sekar

2018

ChemistrySelect

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“…The magnitude of the total static first hyperpolarizability, β tot , calculated as shown in equation (2.5) is a measure of the ease of electron redistribution in a material, in response to an external electric field. βtot=false(βx2+βy2+βz2false)1/2,where β x = ( β xxx + β xyy + β xzz ), β y = ( β yyy + β yzz + β yxx ), β z = ( β zzz + β zxx + β zyy ) and β x , β y and β z are the components of β tot along the x , y and z axes, respectively [5,8,11,29,46].…”

Section: Computational Detailsmentioning

confidence: 99%

In silico screening of ethyl 4-[(E)-(2-hydroxy-4-methoxyphenyl)methyleneamino]benzoate and some of its derivatives for their NLO activities using DFT

et al. 2023

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The nonlinear optical (NLO) properties of ethyl 4-[( E )-(2-hydroxy-4-methoxyphenyl)methyleneamino]benzoate (EMAB) and some of its derivatives are investigated herein using the density functional theory (DFT) and time-dependent (TD)-DFT methods. The density functionals B3LYP, CAM-B3LYP, M06-2X and ω B97XD, and basis sets 6-31 + G**, 6-311 + + G** and Def2-TZVPP have been used. From the results, EMAB and its substituted derivatives studied are promising candidates for NLO materials. In all cases, the static first and second hyperpolarizabilities (31.7–86.5 × 10 −30 and 84.4–273 × 10 −36 electrostatic units (esu), respectively) and the frequency-dependent NLO properties are found to be significantly larger (about 43–103 and 28–76 times greater) than those of the NLO prototypical molecule, para -nitroaniline. Furthermore, the maximum absorption wavelengths of the molecules fall within the UV region of the electromagnetic spectrum. Relative to EMAB, the derivatives have shown improved transparency–nonlinearity trade-offs. Natural bond orbital (NBO) and density of states (DOS) analyses herein revealed effective charge transfer within the molecules studied, especially those with stronger electron donors than that in EMAB (methoxy group). Among the molecules studied, the derivative obtained by substituting EMAB's methoxy group with the pyrrolyl group was found to exhibit the best NLO properties. Conclusively, the NLO activities of EMAB can be significantly improved through the substitution of its methoxy group with stronger electron donors.

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“…Apart from biological properties and applications in pharmacology as active products, or precursors in new, effective pharmaceuticals, which are reported in different comprehensive reviews [16,17], coumarins are characterised by other interesting properties. Notable photophysical properties of coumarins have turned them into extensive dyes for probing, brightening or labelling, as a function of substitution on the core structure and the interaction with the surrounding media [18][19][20][21][22][23][24]. Besides, coumarin compounds are widely used in the laser industry as laser dyes, as well as being reported as dopants in light-emitting diodes (LEDs and OLEDs) [25][26][27][28][29][30][31][32].…”

Section: One Possible Classification Between Different Proposed Subclmentioning

confidence: 99%

Coumarins into Polyurethanes for Smart and Functional Materials

et al. 2020

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Polyurethanes are of undoubted interest for the scientific community and the industry. Their outstanding versatility from tailor-made structures turns them into major polymers for use in a wide range of different applications. As with other polymers, new, emerging molecules and monomers with specific attributes can provide new functions and capabilities to polyurethanes. Natural and synthetic coumarin and its derivatives are characterised by interesting biological, photophysical and photochemical properties. Then, the polyurethanes can exploit those features of many coumarins which are present in their composition to achieve new functions and performances. This article reviews the developments in the proper use of the special properties of coumarins in polyurethanes to produce functional and smart materials that can be suitable for new specific applications.

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Coumarin‐Rhodamine Hybrids – Synthesis, Photophysical Properties, NLO Properties and DFT Studies

Cited by 14 publications

References 79 publications

Tuning ‘Stokes Shift’ and ICT Character by Varying the Donor Group in Imidazo[1,5 a]pyridines: A Combined Optical, DFT, TD‐DFT and NLO Approach

Tuning ‘Stokes Shift’ and ICT Character by Varying the Donor Group in Imidazo[1,5 a]pyridines: A Combined Optical, DFT, TD‐DFT and NLO Approach

In silico screening of ethyl 4-[(E)-(2-hydroxy-4-methoxyphenyl)methyleneamino]benzoate and some of its derivatives for their NLO activities using DFT

Coumarins into Polyurethanes for Smart and Functional Materials

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