Ferrocene analogs of Brooker's merocyanine: a new library of organometallic inverted solvatochromic dyes

Aburto, Ignacio; Martínez‐Gómez, Fabián; Aliaga, Carolina; Domínguez, Moisés

doi:10.1039/d3qo00648d

Cited by 6 publications

(1 citation statement)

References 51 publications

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“…The R substituents modulate the inverted solvatochromism of dyes 2a – c , in terms of both their sensitivity to changes in the solvent polarity and the solvent polarity value at which the inversion point occurs. The sensitivity to changes in solvent polarity is represented by the slope value derived from linear regression for the positive ( m Pos ) and negative ( m Neg ) portions of solvatochromism exhibited . In the positive region, the sensitivity to solvent polarity changes increases in the following order: 2c (R = CF 3 , m Pos = −35.11 kcal mol –1 ) < 2a (R = H, m Pos = −40.34 kcal mol –1 ) < 2b (R = OCH 3 , m Pos = −44.73 kcal mol –1 ).…”

Section: Resultsmentioning

confidence: 99%

Inverting the Solvatochromism of Pyridinium-N-phenolate Dyes by the Addition of a Second Pyridinium Unit

Melinao,

Vidal,

Aliaga

et al. 2024

J. Org. Chem.

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Three bipyridinium phenolates were synthesized, and their spectral behavior was recorded at various solvent polarities and compared to a classic pyridinium phenolate dye possessing only one pyridinium acceptor ring in its structure. The addition of a second pyridinium unit to the classic solvatochromic core results in an unexpected change in the spectral behavior from negative solvatochromism (displacement of the absorption band to shorter wavelengths) to inverted solvatochromism, characterized by the transition from negative to positive solvatochromism (displacement of the absorption band to longer wavelengths) at moderate solvent polarities.

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Section: Resultsmentioning

confidence: 99%