Synthesis, structure, and solvatochromism of merocyanine dyes based on barbituric acid

Kulinich, A. V.; Derevyanko, N. A.; Ishchenko, A. A.

doi:10.1134/s1070363206090167

Cited by 35 publications

(39 citation statements)

References 12 publications

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“…An occasionally described effect when dealing with polyene dyes is inverted solvatochromism, [18][19][20]36] that is, the change from positive to negative solvatochromism with increasing solvent polarity. This phenomenon is ascribed to a solvent-induced change in the ground-state structure from a less dipolar polyene-like structure (non-polar solvents) to a strongly dipolar betaine-like structure (polar solvents), the maximum wavelength being at the cyanine limit.…”

Section: Inverted Solvatochromism?mentioning

confidence: 98%

“…Related barbituric acid derivatives have already been widely used in materials science [e.g., in materials for non-linear optics (NLO)] [15][16][17][18][19] and analysis. [20][21][22][23] The barbiturate moiety also offers the possibility of a facile variation of its electron-demanding effects as well as its interaction with the surroundings by introducing different substituents. In particular, we wanted to determine whether the free NH functions and those capped by alkyl groups have an effect on the chromophoric π-electron system.…”

Section: Introductionmentioning

confidence: 99%

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Differentiating Between Dipolarity and Polarizability Effects of Solvents Using the Solvatochromism of Barbiturate Dyes

et al. 2008

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Section: Inverted Solvatochromism?mentioning

confidence: 98%

Section: Introductionmentioning

confidence: 99%

Differentiating Between Dipolarity and Polarizability Effects of Solvents Using the Solvatochromism of Barbiturate Dyes

et al. 2008

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“…Notwithstanding, the maximum peaks at 391 and 405 nm for poly (chry‐enz) and poly (chry‐ox), respectively, were hypsochromically shifted with a broadened absorption compared with the maximum absorption of CHRY. The reason was that the nitrogen atom lost its free pair of electrons as a result of an intermolecular hydrogen bonding between the ―NH group of polymers and the S═O functional group of DMSO . The observable band broadening for the synthesized polymers as in Figure was prevalent for a π‐delocalized molecule, eventuating that the polymerization was achieved.…”

Section: Resultsmentioning

confidence: 99%

Polymerization of Chrysoidine with chemical and enzymatic oxidative preference: Synthesis, characterization, and spectroscopic study

Kaya

Kolcu

2018

Polymers for Advanced Techs

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Chrysoidine (CHRY) is a type of azo‐dye extensively used in industry. This study delineates 2 routes as enzymatically and oxidatively polycondensation of chrysoidine for the syntheses of poly (chry‐enz) and poly (chry‐ox), respectively. The molecular structures of enzymatically and oxidatively polymerized chrysoidine were described by the FT‐IR, UV‐Vis, 1H‐NMR, and 13C‐NMR techniques. The molecular structures were obtained to be different as in the cyclization process of the enzymatic polymerization. Solvatochromic behavior in selected polar solvents on the optical properties of poly (chry‐ox) were studied. Further characterization was implemented by fluorescence (PL), electrochemical, thermogravimetric (TG‐DTA), cyclic voltammetry (CV), and differential scanning calorimetry (DSC) measurements. The number of average molecular weight of poly(chry‐ox) was found to be higher than that of poly(chry‐enz). Photoluminescence (PL) measurements enlightened the response of poly (chry‐ox) with intense light emissions upon a bicolor irradiation by Ultra‐Violet and visible light. CV technique was utilized to make a comment about HOMO‐LUMO energy levels and electrochemical ( Eg') band gaps of the polymers. Optical and electrochemical band gaps of poly (chry‐enz) were lower than those of poly (chry‐ox), proving the successful synthesis of π‐conjugated structure of poly (chry‐enz). To further make comments about the features of the polymers, scanning electron microscopy (SEM) images were exemplified to study the surface forms of the polymers. Surface morphology of poly (chry‐enz) was seen as agglomerates of grains toward the out‐of‐plane direction. As the polymerization method was changed, the morphology was transformed into a flat‐smooth surface present with visible holes for poly (chry‐ox).

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“…They can be bright, can emit at wavelengths that minimally overlap with cellular autofluorescence, and can exhibit solvent-dependent changes in extinction coefficient, fluorescence quantum yield (QY) or excitation/emission maxima. 11,12 Merocyanine dyes incorporate electron donor and acceptor moieties linked by conjugation. 13 The photophysical properties of the dyes depend on the specific donor/acceptor combination and on the nature of the conjugation.…”

Section: Introductionmentioning

confidence: 99%

Ratiometric Imaging Using a Single Dye Enables Simultaneous Visualization of Rac1 and Cdc42 Activation

et al. 2016

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Biosensors that report endogenous protein activity in vivo can be based on environment-sensing fluorescent dyes. The dyes can be attached to reagents that bind selectively to a specific conformation of the targeted protein, such that binding leads to a fluorescence change. Dyes that are sufficiently bright for use at low, non-perturbing intracellular concentrations typically undergo changes in intensity rather than the shifts in excitation or emission maxima that would enable precise quantitation through ratiometric imaging. We report here mero199, an environment-sensing dye that undergoes a 33-nm solvent-dependent shift in excitation. The dye was used to generate a ratiometric biosensor of Cdc42 (CRIB199) without the need for additional fluorophores. CRIB199 was used in the same cell with a FRET sensor of Rac1 activation to simultaneously observe Cdc42 and Rac1 activity in cellular protrusions, indicating that Rac1 but not Cdc42 activity was reduced during tail retraction, and specific protrusions had reduced Cdc42 activity. A novel program (EdgeProps) used to correlate localized activation with cell edge dynamics indicated that Rac1 was specifically reduced during retraction.

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Synthesis, structure, and solvatochromism of merocyanine dyes based on barbituric acid

Cited by 35 publications

References 12 publications

Differentiating Between Dipolarity and Polarizability Effects of Solvents Using the Solvatochromism of Barbiturate Dyes

Differentiating Between Dipolarity and Polarizability Effects of Solvents Using the Solvatochromism of Barbiturate Dyes

Polymerization of Chrysoidine with chemical and enzymatic oxidative preference: Synthesis, characterization, and spectroscopic study

Ratiometric Imaging Using a Single Dye Enables Simultaneous Visualization of Rac1 and Cdc42 Activation

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