2016
DOI: 10.1039/c6cp03875a
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Reverse solvatochromism in solvent binary mixtures: a case study using a 4-(nitrostyryl)phenolate as a probe

Abstract: A 4-(nitrostyryl)phenolate was synthesized and its use in pure solvents revealed a reversion in solvatochromism. Solutions of a dye in binary solvent mixtures, using as components the solvents in the region of the occurrence of the reversion, provided the first case in the literature of reverse solvatochromism in a binary mixture.

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Cited by 15 publications
(11 citation statements)
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“…Figure shows a plot of the transition energies obtained as a function of the E T (30) solvent polarity values for dye 13 b , these being similar to those obtained for the other dyes (Figure S45 in the Supporting Information). In all cases, an inverted behavior was observed, as previously described for analogous dyes 5 . As a typical example, for dye 7 b , the solvatochromic band has a maximum at 573 nm [ E T ( 7 b )=49.9 kcal mol −1 ] in n ‐hexane (the least polar solvent studied), whereas in DMSO λ max =798 nm [ E T ( 7 b )=35.8 kcal mol −1 ].…”
Section: Resultssupporting
confidence: 68%
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“…Figure shows a plot of the transition energies obtained as a function of the E T (30) solvent polarity values for dye 13 b , these being similar to those obtained for the other dyes (Figure S45 in the Supporting Information). In all cases, an inverted behavior was observed, as previously described for analogous dyes 5 . As a typical example, for dye 7 b , the solvatochromic band has a maximum at 573 nm [ E T ( 7 b )=49.9 kcal mol −1 ] in n ‐hexane (the least polar solvent studied), whereas in DMSO λ max =798 nm [ E T ( 7 b )=35.8 kcal mol −1 ].…”
Section: Resultssupporting
confidence: 68%
“…The above arguments and evidence can be used to interpret the observed solvatochromic inversion of these "hybrid cyanine" dyes in solutions of mediump olarity.I nspite of their structuralv ariations, this family of compounds exhibit as olvatochromic reversion in an arrow region of solvent polarities, characterized by intermediate E T N values (0.4-0.5). [10,11] Minimum E T values are verifiedw ith the same group of solvents, all of them showing negligible acidity,a nd significant dipolaritypolarizability,a nd basicity. Medium acidity clearly increases the internal CT energy by partially protonating the phenolate oxygen donor (in the case of hydrogen-bondd onating solvents), or by reducing its charget hrough associationw ith a cationic electrophile, as occurs with a" co-solvent"s uch as NaPh 4 B.…”
Section: Analysis Of the Influence Of The Solvent Properties On The Rmentioning
confidence: 77%
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