Fluorosolvatochromism of furanyl- and thiophenyl-substituted acetophenones

Friebe, Nadine; Schreiter, Katja; Kübel, Joachim; Dietzek, Benjamin; Moszner, Norbert; Burtscher, Peter; Oehlke, Alexander; Spange, Stefan

doi:10.1039/c5nj00256g

Cited by 16 publications

(8 citation statements)

References 49 publications

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“…In all cases, the plots of the solvent parameters versus the emission energy do not disclose an obvious relationship. This behavior is in agreement with that of other donor–acceptor biaryl-type dyes, such as for example para -hetaryl-substituted benzophenone derivatives, whose emission properties were demonstrated to depend on a complex interplay of different solvent parameters [ 38 ]. Unfortunately, the limited solubility of the derivatives 6b – e did not permit to employ a large series of solvents that is required for such a multiparameter analysis of these compounds.…”

Section: Discussionsupporting

confidence: 87%

Synthesis and fluorosolvatochromism of 3-arylnaphtho[1,2-b]quinolizinium derivatives

Pithan¹,

Decker²,

Sardo³

et al. 2016

Beilstein J. Org. Chem.

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SummaryCationic biaryl derivatives were synthesized by Suzuki–Miyaura coupling of 3-bromonaphtho[1,2-b]quinolizinium bromide with arylboronic acids. The resulting cationic biaryl derivatives exhibit pronounced fluorosolvatochromic properties. First photophysical studies in different solvents showed that the emission energy of the biaryl derivatives decreases with increasing solvent polarity. This red-shifted emission in polar solvents is explained by a charge shift (CS) in the excited state and subsequent solvent relaxation. Furthermore, the polarity of protic polar and aprotic polar solvents affects the emission energy to different extent, which indicates a major influence of hydrogen bonding on the stabilization of the ground and excited states.

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Section: Discussionsupporting

confidence: 87%

Synthesis and fluorosolvatochromism of 3-arylnaphtho[1,2-b]quinolizinium derivatives

Pithan¹,

Decker²,

Sardo³

et al. 2016

Beilstein J. Org. Chem.

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“…These compounds exhibited strong uorosolvatochromism, as a result of the substantial photoinduced ICT process. Another study using thiophene ring as electron donating group for thiophenylsubstituted acetophenone was given by Friebe et al; 17 where the uorescence emission spectra were found to depend on the nature of the solvent, and the uorosolvatochromism were observed in wide range of solvents of different acidity, basicity and polarity. It is well known that 2,5-thienylene derivatives exhibit less extended emission solvatochromic range than 1,4phenylene analogues even if the ICT is more important in the rst case.…”

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confidence: 99%

Photophysical properties and fluorosolvatochromism of D–π–A thiophene based derivatives

et al. 2020

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“…To understand the contribution of different aspects of solute‐solvent intermolecular interactions, spectral shift of this chromophoric dye observed in 20 different pure solvents is correlated with solvent property parameters using linear solvation energy relationship (LSER) multiparametric approaches . Two most widely employed LSER i. e. Kamlet‐Taft and Catalan equations, which considers solvent properties such as, HBD acidity, HBA basicity, dipolarity and polarizability have been used in the present study . To study the major contribution from any other solvent polarity parameters such as dipole moment, dielectric constant, electron pair donor/acceptor capabilities, hydrophobicity/hydrophilicity etc.…”

Section: Introductionmentioning

confidence: 99%

D‐π‐A Molecular Probe to Unveil the Role of Solute‐Solvent Hydrogen Bonding in Solvatochromism, Location Specific Preferential Solvation and Synergistic Effect in Binary Mixtures

2020

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An azo dye 4‐(p‐Nitrophenylazo) phenol (NPAP) characterized with a donor‐π‐acceptor (D‐π‐A) framework has been used as a molecular probe to study solvatochromic behavior in neat and binary solvent mixtures comprised of chloroform (a hydrogen bond donor; HBD solvent) and a hydrogen bond acceptor (HBA) solvent. The specificity of the probe lies in its inherent characteristics of having a HBD group and a HBA group at two different ends of the conjugated π‐network. UV‐Vis spectroscopic technique is used for the purpose. The probe demonstrates a very expressive reversal in solvatochromic behavior, with the solvatochromic switch at ET(30) of ∼45 kcal mol−1. Multiparametric treatment of the solvatochromic data using SEV technique displays excellent sensitivity of the probe towards HBA basicity, dipolarity and polarizability of the medium with a smaller but significant contribution from HBD acidity and hydrophobicity/apolarity. The event of preferential solvation in the chloroform‐HBA mixture is explained on the basis of specific solute‐solvent interaction through HBD and HBA ability of the solvent components. HBA solvents preferentially solvate the phenolic site while HBD solvents preferentially solvate the nitrobenzene group through complementary hydrogen bonding, which results in an increase in local concentration at specific sites resulting in synergistic preferential solvation. The proposition of site selective PS through molecular recognition is also supported by theoretical studies.

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Fluorosolvatochromism of furanyl- and thiophenyl-substituted acetophenones

Abstract: Fluorosolvatochromism of four furanyl- or thiophenyl-substituted acetophenone derivatives is suitable to measure environmental effects.

Cited by 16 publications

References 49 publications

Synthesis and fluorosolvatochromism of 3-arylnaphtho[1,2-b]quinolizinium derivatives

Synthesis and fluorosolvatochromism of 3-arylnaphtho[1,2-b]quinolizinium derivatives

Photophysical properties and fluorosolvatochromism of D–π–A thiophene based derivatives

D‐π‐A Molecular Probe to Unveil the Role of Solute‐Solvent Hydrogen Bonding in Solvatochromism, Location Specific Preferential Solvation and Synergistic Effect in Binary Mixtures

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