Negative solvatochromism of a series of pyridinium phenolate betaine dyes with increasing steric hindrance

Jacques, Patrice; Graff, Bernadette; Diemer, Vincent; Ay, Emel; Chaumeil, Hélène; Carré, Christiane; Malval, Jean‐Pierre

doi:10.1016/j.cplett.2012.02.018

Cited by 29 publications

(27 citation statements)

References 14 publications

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“…Compounds 2 , 3 , 4 , 5 (Scheme ) have been prepared and their solvatochromic behaviour related with the increasing steric hindrance between the donor and acceptor rings, towards orthogonality …”

Section: Resultsmentioning

confidence: 99%

“…Related pyridinium phenolate betaine dyes 2 , 3 , 4 , 5 with increasing steric hindrance, towards orthogonality, between the donor and acceptor ring fragments …”

Section: Resultsmentioning

confidence: 99%

“…As found by the authors, none of the plots of E T vs. E T N are linear. In consequence, two straight lines were drawn for each compound, corresponding to two different solvatochromic responses, in HBD and non‐HBD solvents …”

Section: Resultsmentioning

confidence: 99%

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A generalized reversal model for the solvatochromism of merocyanines

Rezende

2016

J. Phys. Org. Chem.

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The solvatochromic behaviour of merocyanines can be interpreted and predicted by consideration of their molecular structure with the aid of a model that regards all kinds of solvatochromism as particular cases of a generalized reverse behaviour. This generalized reversal model is shown to be consistent with the cyanine-limit model, another independent approach that relates the merocyanine structure with its solvatochromic behaviour. Both models are validated by experimental data from the literature of 21 merocyanines of variable molecular structure.

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Section: Resultsmentioning

confidence: 99%

“…Related pyridinium phenolate betaine dyes 2 , 3 , 4 , 5 with increasing steric hindrance, towards orthogonality, between the donor and acceptor ring fragments …”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

A generalized reversal model for the solvatochromism of merocyanines

Rezende

2016

J. Phys. Org. Chem.

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“…10 Second, hydrogen bonds are readily formed between the negative oxygen atom of phenolate functionality and water or hydroxyl groups of linear alcohols. 11 These drawbacks may be avoided by introducing bulky groups at the ortho position of the phenolate. [4][5][6][7][8][9][10][11][12] In this context, we have recently synthesised pyridinium phenolates bearing saturated handles of various lengths (compounds 1a-d, Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

“…11 These drawbacks may be avoided by introducing bulky groups at the ortho position of the phenolate. [4][5][6][7][8][9][10][11][12] In this context, we have recently synthesised pyridinium phenolates bearing saturated handles of various lengths (compounds 1a-d, Scheme 1). 13 A moderate twist angle was introduced by anchoring two methyl groups at the meta position of the pyridine ring to retain reasonable NLO responses.…”

Section: Introductionmentioning

confidence: 99%

Concerning restricted rotations in pyridinyl anisoles and pyridinyl phenols bearing saturated handles, and their solid state structures

Nouën

Chaumeil

et al. 2014

Tetrahedron Letters

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Charge‐Transfer‐Adaptable Double‐Strand Formation of a Porphyrin‐BODIPY‐Porphyrin Triad

2021

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A quadrupolar porphyrin-BODIPY-porphyrin array (1) displayed a moderate negative solvatochromism. The elastic 3,4,5-tri((S)dihydrocitronellyloxy)phenyl groups of 1 facilitated the solubility of such a polarized chromophore array in a nonpolar solvent, and 1 was assembled into a double-strand as elucidated by extensive NMR spectroscopic experiments in [D 8 ]toluene and electronic absorption spectra in cyclohexane. Thermodynamic analyses revealed a small entropy change upon double-strand formation, indicating that cyclohexane did not preferably solvate the porphyrin rings and BODIPY segment presumably because of their polarized nature. At the same time, the significant enthalpy change likely explained the intermolecular attractive force, such as the BF 2 •••Zn cation-dipole interaction. The solvent polarity effect on the electronic spectra together with thermodynamic analyses suggested that the charge-transfer (CT) character was decreased by the double-strand formation in a nonpolar solvent. It was rationalized that insufficient solvent polarity stabilized the CT character of 1 only in part, and the residual polarization character might be stabilized by supramolecular assembly. The charge transfer character of 1 was stabilized by double-strand formation which partially decreased the CT character enough to be stabilized by solvation with cyclohexane.

show abstract

Negative solvatochromism of a series of pyridinium phenolate betaine dyes with increasing steric hindrance

Cited by 29 publications

References 14 publications

A generalized reversal model for the solvatochromism of merocyanines

A generalized reversal model for the solvatochromism of merocyanines

Concerning restricted rotations in pyridinyl anisoles and pyridinyl phenols bearing saturated handles, and their solid state structures

Charge‐Transfer‐Adaptable Double‐Strand Formation of a Porphyrin‐BODIPY‐Porphyrin Triad

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