Solvatochromism: a tool for solvent discretion for UV-Vis spectroscopic studies

Karmakar, Neeraj Kumar; Pandey, Swati; Pandey, Ravindra Kumar; Shukla, Shiv Shankar

doi:10.1080/05704928.2020.1838918

Cited by 27 publications

(9 citation statements)

References 38 publications

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“…The effect of bulk solvent polarity was approximated by the Conductorlike polarizable continuum model (CPCM) that correlates the properties of the solvents as the dielectric constant and refraction index to generate a potential surface and optimize the ground state geometries without considering specific interactions such as hydrogen bonds [46]. In the present study, the vertical excitation and frequencies of the molecules were treated with PBE0/aug-cc-pVDZ which was a functional and basis set that represented quite well the experimental data.…”

Section: Dft/td-dft Calculationmentioning

confidence: 99%

Synthesis, photophysics, and theoretical calculations of styryl-based fluorophores harboring substituted benzothiazole acceptors

Filho

Moraes²,

Luz³

et al. 2023

Journal of Photochemistry and Photobiology A: Chemistry

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Section: Dft/td-dft Calculationmentioning

confidence: 99%

Synthesis, photophysics, and theoretical calculations of styryl-based fluorophores harboring substituted benzothiazole acceptors

Filho

Moraes²,

Luz³

et al. 2023

Journal of Photochemistry and Photobiology A: Chemistry

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“…Apart from being sensitive to the polarity of the environment, these materials can also be involved in solvent specific supramolecular interactions such as hydrogen bonding. This leads to their application not just as solvent polarity sensors but also as probes to study solvent effects in organic chemistry and supramolecular chemistry, for chemical sensing, − as well as for examining biological processes. − …”

Section: Introductionmentioning

confidence: 99%

Amplifying the Negative Solvatochromism of Pyridinium Phenolates via Fluorene Conjugation

Zharinova,

Saker Neto,

Wong

2023

Chem. Mater.

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New chromophores carrying a donor phenolate group and an acceptor pyridyl moiety separated by a fluorene spacer are reported. A progressive elongation of the systems was achieved by the introduction of an additional phenyl ring and one or two vinyl linkers using Suzuki−Miyaura or Horner−Wadsworth−Emmons couplings. Zwitterionic forms FL1−FL5 of these donor−bridge−acceptor molecules were generated through consequent N-methylation and deprotonation reactions leading to large redshifts in absorbance maxima. UV−vis absorbance studies also revealed a negative solvatochromic behavior, with a smooth bathochromic shift observed upon decreasing the solvent polarity. Notably, examples FL1a and FL3 exhibited wide solvatochromic shifts of 235 and 297 nm, respectively, as the solvent polarity gradually lowered from polar water to less polar pyridine. Remarkably, the magnitude of the shift for FL3 was even greater than that of Reichardt's dye (253 nm) in the same solvent range, which is known to be one of the best performing solvatochromic dyes reported. Apart from extending the conjugation, the fluorene moiety also allows facile side chain engineering, making these solvatochromic dyes attractive candidates for medium-polarity indicators and sensors.

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“…Solvatochromism, the dependence of the absorption wavelength of a dye with respect to the solvent in which it is solvated [ 1 , 2 , 3 , 4 , 5 ], is a tool that is widely used for the study of the nature of the solvation environment. Although it was developed for the study of bulk solvents, it was later extended to more structured contexts such as membranes, micelle, etc.…”

Section: Introductionmentioning

confidence: 99%

“…Although it was developed for the study of bulk solvents, it was later extended to more structured contexts such as membranes, micelle, etc. [ 5 ].…”

Section: Introductionmentioning

confidence: 99%

A Specific Interaction between Ionic Liquids’ Cations and Reichardt’s Dye

et al. 2022

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Solvatochromic probes are often used to understand solvation environments at the molecular scale. In the case of ionic liquids constituted by an anion and a cation, which are designed and paired in order to obtain a low melting point and other desirable physicochemical properties, these two indivisible components can interact in a very different way with the probe. This is the case with one of the most common probes: Reichardt’s Dye. In the cases where the positive charge of the cation is delocalized on an aromatic ring such as imidazolium, the antibonding orbitals of the positively charged aromatic system are very similar in nature and energy to the LUMO of Reichardt’s Dye. This leads to an interesting, specific cation-probe interaction that can be used to elucidate the nature of the ionic liquids’ cations. Parallel computational and experimental investigations have been conducted to elucidate the nature of this interaction with respect to the molecular structure of the cation.

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Solvatochromism: a tool for solvent discretion for UV-Vis spectroscopic studies

Cited by 27 publications

References 38 publications

Synthesis, photophysics, and theoretical calculations of styryl-based fluorophores harboring substituted benzothiazole acceptors

Synthesis, photophysics, and theoretical calculations of styryl-based fluorophores harboring substituted benzothiazole acceptors

Amplifying the Negative Solvatochromism of Pyridinium Phenolates via Fluorene Conjugation

A Specific Interaction between Ionic Liquids’ Cations and Reichardt’s Dye

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