Investigation of contrasting hydrogen bonding pattern of 3-(phenylamino)-cyclohexen-1-one with solvents in the ground and excited states

Misra, Ramprasad; Kar, Susmita

doi:10.1016/j.chemphys.2012.01.001

Cited by 18 publications

(7 citation statements)

References 55 publications

(84 reference statements)

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“…[41][42][43][44] We have shown earlier that solvents play a major role in shaping the photophysical properties of PACO. 25,[45][46][47][48] To understand the role of solvents in shaping the absorption spectra of OACO and NACO, we have theoretically simulated their absorption spectra in water. The ground state geometries of PACO, OACO and NACO have been optimized fully in the gas phase.…”

Section: A Absorption Spectra Of Paco Oaco and Naco In Different Solv...mentioning

confidence: 99%

Tailoring of spectral response and intramolecular charge transfer in β-enaminones through band gap tuning: synthesis, spectroscopy and quantum chemical studies

et al. 2016

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In this paper, we investigate the synthetic tailoring of the spectral response and intramolecular charge transfer (ICT) of b-enaminones through bandgap modulation. Two donor/acceptor substituted benaminones, namely, 3-(4-methoxyphenylamino)-2-cyclohexen-1-one (OACO) and 3-(4nitrophenylamino)-2-cyclohexen-1-one (NACO) have been synthesized along with their unsubstituted counterpart, 3-(phenylamino)-2-cyclohexen-1-one (PACO). Steady state as well as time resolved spectroscopic techniques with picosecond resolution are used to record their spectral responses. Substitution of the donor group (-OCH 3 ) mildly enhances the charge transfer from the phenyl ring to the enaminone moiety, while substitution of the acceptor group (-NO 2 ) jeopardizes the charge transfer through mutual electron withdrawing effects of PNA and enaminone moieties. Combined experimental and quantum chemical investigations reveal that the ground state photophysics of OACO and NACO in water are controlled by both microscopic and macroscopic solvation with dominant contribution from the former. Time dependent density functional theory (TDDFT) calculations predict that the HOMO to[LUMO+1] transition gives rise to the absorption spectra of OACO in water, while the absorption by the enaminone moiety of NACO arises as a result of a HOMO to LUMO transition. A crossing between the first (S 1 ) and the second excited (S 2 ) states takes place in the microclusters of PACO, OACO and NACO with water. The intersystem crossing (ISC) has been found to be the major reason for low quantum yields in these molecules. The band gap modulation through waxing and waning of the conjugation strength is expected to throw light on many ICT-driven processes and provides means of tuning the properties depending on it.

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Section: A Absorption Spectra Of Paco Oaco and Naco In Different Solv...mentioning

confidence: 99%

Tailoring of spectral response and intramolecular charge transfer in β-enaminones through band gap tuning: synthesis, spectroscopy and quantum chemical studies

et al. 2016

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“…In polar solvents, like, alcohols, DMSO and water, dual emission was observed. Our previous studies [25][26][27][28] led us to conclude that the absorption excites PACO to the S 2 (pp*) state while the dual emission presumably arises from a locally excited (S 1 -LE, np*) state and an ICT state (S 1 -ICT, np*) formed due to excitation by light. The mechanism of the ICT process has been investigated using steady-state and time-resolved spectroscopic techniques in conjunction with quantum chemical calculations.…”

Section: Introductionmentioning

confidence: 95%

“…The mechanism of the ICT process has been investigated using steady-state and time-resolved spectroscopic techniques in conjunction with quantum chemical calculations. It turns out that the medium plays an important role in shaping the electronic structure and the photophysics of the probe [26][27][28].…”

Section: Introductionmentioning

confidence: 99%

Interplay of micro- and macroscopic solvation in spectral responses of PACO in 1,4-dioxane–water mixtures: A combined experimental and quantum chemical analysis

Misra

Chakraborty

Roy

et al. 2015

Journal of Photochemistry and Photobiology A: Chemistry

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“…Where, I 0 and I are the steady‐state fluorescence intensities in the absence and presence of quencher, respectively, K SV is the Stern‐Volmer quenching constant, τ q is the average lifetime of the protein without the quencher, and [Q] is the concentration of the quencher (T CN P). The K SV value was determined by plotting I 0 /I at 340 nm against the probe concentration (Figure 2D) and was found to be 5.26×10 5 M −1 as measured by the linear regression assessment, which ensures effective interaction between BSA and T CN P. BSA O accounts for several pathological conditions in the body, [60] and investigating the ability of the probe to interact with BSA O is of great interest. To assess the interaction, the native BSA was subjected to oxidation by incubating BSA (10 μM) with hydrogen peroxide (H 2 O 2 , 100 μM), ferrous sulfate (FeSO 4 , 10 μM) and EDTA (10 μM) in PBS at room temperature in the dark.…”

Section: Figurementioning

confidence: 99%

Benzothiazole‐Phenothiazine Conjugate Based Molecular Probe for the Differential Detection of Glycated Albumin

Kumar

Datta

Samanta

et al. 2021

Israel Journal of Chemistry

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Glycation of albumin proteins is considered the pathophysiological hallmark of several chronic fatal disorders, including diabetes mellitus (DM) and Alzheimer's disease (AD). The optical detection of glycated albumin is a simple and cost‐effective tool with diagnostic implications for DM and AD. Herein, we developed a cyano derivative of the benzothiazole‐phenothiazine conjugate (TCNP) ‐based far‐red fluorescence probe for the differential detection of glycated bovine serum albumin (BSAG) over native BSA and oxidized BSA (BSAO). The selective fluorescence enhancement of TCNP in the presence of native BSA and BSAO and significant quenching in the presence of BSAG account for the distinct interaction between the probe and different structural variants of BSA. The high photostability and differential response towards native BSA and BSAG infer that TCNP is a potential molecular tool to assess the glycation induced structural changes of albumins.

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Investigation of contrasting hydrogen bonding pattern of 3-(phenylamino)-cyclohexen-1-one with solvents in the ground and excited states

Cited by 18 publications

References 55 publications

Tailoring of spectral response and intramolecular charge transfer in β-enaminones through band gap tuning: synthesis, spectroscopy and quantum chemical studies

Tailoring of spectral response and intramolecular charge transfer in β-enaminones through band gap tuning: synthesis, spectroscopy and quantum chemical studies

Interplay of micro- and macroscopic solvation in spectral responses of PACO in 1,4-dioxane–water mixtures: A combined experimental and quantum chemical analysis

Benzothiazole‐Phenothiazine Conjugate Based Molecular Probe for the Differential Detection of Glycated Albumin

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