The inverted solvatochromism of protonated ferrocenylethenyl-pyrimidines: the first example of the solvatochromic reversal of a hybrid organic/inorganic dye
Literature Information
Publication Date
2019-09-30
DOI
10.1039/C9QO01043B
Impact Factor
5.281
Authors
Matías Vidal, Marcos Caroli Rezende, Moisés Domínguez
View Original
Abstract
Five new solvatochromic 2,6-diaryl-4-ferrocenylethenylpyrimidines were synthesized and their spectral variations in solution investigated in twenty-seven solvents of variable polarity. Their observed positive solvatochromism in HBD- and non-HBD-solvents changed to an inverted behavior upon protonation of the pyrimidine ring by the addition of trifluoroacetic acid. Multiparametric analysis of the solvatochromic band of the protonated dyes showed that the solvent acidity and polarizability were mainly responsible for their inverted behavior, which arose from an internal charge-transfer from the ferrocene fragment to the pyrimidinium acceptor, confirmed by theoretical calculations.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
Recommended Compounds
BIS(I-PROPYLCYCLOPENTADIENYL)TITANIUM DICHLORIDE
CAS Number:
12130-65-3
Molecular Formula:
C16H22Cl2Ti
![(1R,6R)-6-({[(2-Methyl-2-propanyl)oxy]carbonyl}amino)-3-cyclohexene-1-carboxylic acid structure](https://static.chemtradehub.com/structs/865/865689-24-3-5fef.webp "(1R,6R)-6-({[(2-Methyl-2-propanyl)oxy]carbonyl}amino)-3-cyclohexene-1-carboxylic acid structure")
(1R,6R)-6-({[(2-Methyl-2-propanyl)oxy]carbonyl}amino)-3-cyclohexene-1-carboxylic acid
CAS Number:
865689-24-3
Molecular Formula:
C12H19NO4
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