Tuning of hyperpolarizability, and one- and two-photon absorption of donor–acceptor and donor–acceptor–acceptor-type intramolecular charge transfer-based sensors

Samanta, Pralok K.; Alam, Md. Mehboob; Misra, Ramprasad; Pati, Swapan K.

doi:10.1039/c9cp03772a

Cited by 27 publications

(12 citation statements)

References 64 publications

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“…Besides, the usage of different functional groups has offered the organic molecular materials with exceptional and fascinating optoelectronic properties . In this context, D–A-based materials have gained considerable attention as promising candidates for VOCs detection. , Several D–A-based molecules have been developed to achieve a π-conjugated backbone, which aids high crystallinity in thin films. Generally, π-conjugated backbone structures critically affect the solubility, co-planarity, energy levels, and molecular packing.…”

Section: Introductionmentioning

confidence: 99%

Tuning the π-Conjugation of 2-Thiohydantoins toward a Rigorously Defined Detection of Volatile Organic Compounds by Surface Photovoltage

Gawas

Bora

Reji

et al. 2022

ACS Appl. Electron. Mater.

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The design of portable devices by immobilization of sensory probes using donor−acceptor (D−A) architectures enables the visual detection and onsite analysis of volatile organic compounds (VOCs). In this work, we have reported on the synthesis of different D−A architectures of 2-thiohydantoin (2TH) derivatives by extending the conjugation with phenyl (Ph-2TH), naphthalene (Naptha-2TH), and anthracene (Anthra-2TH) moieties at the C 5 position. Single-crystal X-ray analysis reveals that extending the conjugation leads to variation in the molecular arrangement in the crystal lattice. Ph-2TH and Naptha-2TH show ribbon-like self-assembled layered arrangements, whereas Anthra-2TH crystallized in herringbone packing in the crystal lattice. The C−S•••H interactions were varied with interatomic distances of 2.67, 2.63, and 2.27 Å, respectively, for phenyl, naphthalene, and anthracene. The photophysical and excited-state gas-phase interactions using scanning kelvin probe studies reveal that 2TH ensembles alter their surface photovoltages toward recognition of different VOCs (like ethanol, acetone, toluene, triethylamine, nonanal, and chloroform) depending on their donor and acceptor nature. All three 2TH derivatives showed n-type behavior with high selectivity toward nonanal, and Anthra-2TH exhibited high response (91.02%) within 278 s as well as recovery (92.83%) in surface photovoltages in 647 s. Combined experimental and computational studies demonstrate that the aromatic moieties appended 2TH ensembles would be an efficient D−A ensemble for the detection of VOCs containing carbonyl and alcohol functionalities aiding strong intermolecular interactions.

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Section: Introductionmentioning

confidence: 99%

Tuning the π-Conjugation of 2-Thiohydantoins toward a Rigorously Defined Detection of Volatile Organic Compounds by Surface Photovoltage

Gawas

Bora

Reji

et al. 2022

ACS Appl. Electron. Mater.

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“…The blue areas represent the loss of electronic and the green areas represent the obtain of electronic. This method has been proved to be an available and useful way. − It is demonstrated that the charge transfer process has a considerable variation before and after reaction with ONOO – . Taking the probe as an example, we can see that the blue and green areas show overlapping in general, which means that the charge transfer is not obvious.…”

Section: Resultsmentioning

confidence: 99%

Effect of a Hydrogen Bond on Molecular Probing Properties in the Solvent

et al. 2019

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Hydrogen bond (HB) is of an important factor on theory. In this work, the effect of a solvent on the performance of a newly synthesized fluorescent probe for detecting endogenous ONOO– is studied by using four different solvent models, noted as polarizable continuum model (PCM), ONIOM, HB, and HB + PCM models, respectively, where HB contribution is thus given special attention. The theoretical results show that the absorption and emission properties of the probe are obviously influenced by the HB; for example, the HB + PCM model including both short- and long-range interactions between the solute and solvent molecules gives the exact description on the solvent effect. In particular, the responsive mechanism of the probe for sensing ONOO– is explored by analyzing the charge variations between the excited states and ground states of the free molecules and their reaction products. It is demonstrated that the mechanism is attributed to an intramolecular charge transfer, where the HB has an important contribution. Moreover, the influence of HB on a two-photon absorption cross section has been considered. Our investigation reveals that the HB has an important influence on the optical properties and responsive mechanism of the fluorescent probe, and it must be considered for theoretical calculations.

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“…[35][36][37] The sensing mechanism is mediated by intramolecular charge transfer (ICT) between the donor and acceptor due to the D-π-A motif characteristics of hemicyanine. 38,39 The hemicyanine scaffold is covalently attached to a specific response moiety, which reduces the electron-donating ability of the donor, resulting in ICT blocking and fluorescence quenching. 30,40,41 Upon exposure to the targeted biomarkers, the response moiety is selectively removed to restore the fluorescence.…”

Section: Introductionmentioning

confidence: 99%

An activatable near-infrared hemicyanine-based probe for selective detection and imaging of Hg²⁺ in living cells and animals

Chen

et al. 2022

Analyst

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Tuning of hyperpolarizability, and one- and two-photon absorption of donor–acceptor and donor–acceptor–acceptor-type intramolecular charge transfer-based sensors

Abstract: Effect of solvent as well as arrangement of donor–acceptor groups on the linear and non-linear optical (NLO) response properties of two intramolecular charge-transfer (ICT)-based fluorescent sensors are studied.

Cited by 27 publications

References 64 publications

Tuning the π-Conjugation of 2-Thiohydantoins toward a Rigorously Defined Detection of Volatile Organic Compounds by Surface Photovoltage

Tuning the π-Conjugation of 2-Thiohydantoins toward a Rigorously Defined Detection of Volatile Organic Compounds by Surface Photovoltage

Effect of a Hydrogen Bond on Molecular Probing Properties in the Solvent

An activatable near-infrared hemicyanine-based probe for selective detection and imaging of Hg²⁺ in living cells and animals

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Tuning of hyperpolarizability, and one- and two-photon absorption of donor–acceptor and donor–acceptor–acceptor-type intramolecular charge transfer-based sensors

Abstract: Effect of solvent as well as arrangement of donor–acceptor groups on the linear and non-linear optical (NLO) response properties of two intramolecular charge-transfer (ICT)-based fluorescent sensors are studied.

Cited by 27 publications

References 64 publications

Tuning the π-Conjugation of 2-Thiohydantoins toward a Rigorously Defined Detection of Volatile Organic Compounds by Surface Photovoltage

Tuning the π-Conjugation of 2-Thiohydantoins toward a Rigorously Defined Detection of Volatile Organic Compounds by Surface Photovoltage

Effect of a Hydrogen Bond on Molecular Probing Properties in the Solvent

An activatable near-infrared hemicyanine-based probe for selective detection and imaging of Hg2+ in living cells and animals

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Product

Resources

About

An activatable near-infrared hemicyanine-based probe for selective detection and imaging of Hg²⁺ in living cells and animals