Fluorescent difluoroboron-curcumin analogs: An investigation of the electronic structures and photophysical properties

Margar, Sachin N.; Rhyman, Lydia; Ramasami, Ponnadurai; Sekar, Nagaiyan

doi:10.1016/j.saa.2015.07.064

Cited by 49 publications

(19 citation statements)

References 54 publications

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“…Relative orientation in such systems can enhance the first hyperpolarizability (β 0 ). A recent study on boron complexes of curcumin analogs and previous reports on the boron complexes of the push‐pull based bisboronate chromophore and boron complexes obtained from hydroxyl chalcones have suggested that the boron complexes can be a promising candidate as NLO materials ,…”

Section: Resultsmentioning

confidence: 92%

“…Difluoroboron complexes are known to possess excellent electron‐accepting properties which lead to strong fluorescence with high quantum yields. Curcumin skeleton has been studied for the NLO properties including their symmetric, and asymmetric, analogs as well as the metal complex of curcumin ,. Recently, difluoroboron curcumin analog have also being investigated for their NLO properties …”

Section: Introductionmentioning

confidence: 99%

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Theoretical Investigation of Difluoroboron Complex of Curcuminoid Derivatives with and without Phenyl Substituent (at Meso Position): Linear and Non‐Linear Optical Study

et al. 2018

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Two difluoroboron curcumin analogs and their phenylated versions were studied for their photophysical and non-linear optical properties based on comprehensive density functional theory approach. The ground state geometry optimization, vertical excitation, and the first excited state optimization were carried out using B3LYP and CAMÀ B3LYP functionals with 6-31G(d) basis set. The geometry of the difluoroboron curcumin analogs was found to remain planar in both the ground and excited states. The computed vertical excitation and emission values obtained with global hybrid functional are in good correlation with the observed values. The phenylated analogs show enhancement in the photophysical properties. The linear and non-linear optical properties were computed using two global hybrids functionals (B3LYP and BHHLYP) and a range separated hybrid functional (CAMÀ B3LYP) with 6-31 + G(d,p) basis set. The difluoroboron curcumin analogs without the phenyl substituent have larger polarizability and hyperpolarizabiliy parameters than the phenylated analogs. The polarizability and hyperpolarizabiliy were found to be comparable with the BHHLYP and CAMÀ B3LYP functionals.[a] M. M. Raikwar, Prof. N. Sekar

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Section: Resultsmentioning

confidence: 92%

Section: Introductionmentioning

confidence: 99%

Theoretical Investigation of Difluoroboron Complex of Curcuminoid Derivatives with and without Phenyl Substituent (at Meso Position): Linear and Non‐Linear Optical Study

et al. 2018

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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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“…The parameters ( μ, α 0 , Δα, β 0 , γ ) of polarizability and hyperpolarizability have been calculated using density functional theory (DFT) with CAM−B3LYP/6‐311+G(d,p) basis set on the basis of finite‐field approach . The expression Eqn.…”

Section: Resultsmentioning

confidence: 99%

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

Shreykar

Sekar

2017

ChemistrySelect

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Solvatochromic and solvatofluoric behaviour of three coumarin rhodamine hybrid dyes (Cou‐Rhod1, Cou‐Rhod2 and Cou‐Rhod3) have been studied in ten different solvents with varying polarity. The pH (1‐10) study was done to investigate the spirocyclic ring opening. All the dyes show charge transfer phenomenon in local as well as charge transfer excitation. The non‐linear optical properties of coumarin rhodamine hybrid dyes were studied using solvatochromic method (highest value of αCT for Cou‐Rhod1=2.44 X 10−23; highest value of βCT for Cou‐Rhod2=0.14 X 10−28 and the highest value of γ for Cou‐Rhod2=0.02 X 10−34) and computational (highest value of α0 for Cou‐Rhod3=9.89 X 10−23; highest value of β0 for Cou‐Rhod1=0.90 X 10−28 and highest value of γ for Cou‐Rhod3=5.10 X 10−34) approach. As the non‐radiative rate constant increases quantum yield of the dyes decreases. Correlation of calculated radiative lifetime (τ), radiative (Kr) and non‐radiative rate constant (Knr) has been made to explain the quantum yield of dyes using Strickler‐Berg equation. The charge transfer behaviour, structural parameters and non‐linear optical properties of the dyes are well described by DFT and TD‐DFT calculations.

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Fluorescent difluoroboron-curcumin analogs: An investigation of the electronic structures and photophysical properties

Cited by 49 publications

References 54 publications

Theoretical Investigation of Difluoroboron Complex of Curcuminoid Derivatives with and without Phenyl Substituent (at Meso Position): Linear and Non‐Linear Optical Study

Theoretical Investigation of Difluoroboron Complex of Curcuminoid Derivatives with and without Phenyl Substituent (at Meso Position): Linear and Non‐Linear Optical Study

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

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

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