Dependence of metal ion complexation and intermolecular aggregation on photoinduced geometric isomerism in a crown ether styryl dye

Barzykin, A. V.; Fox, Marye Anne; Ushakov, Evgeny N.; Stanislavskii, O. B.; Gromov, S. P.; Федорова, О. А.; Алфимов, М. В.

doi:10.1021/ja00042a013

Cited by 63 publications

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“…Most of the known macrocyclic chromo- and fluoroionophores with a styryl moiety ,− were designed by using a common principle, namely, by combining a macrocycle (usually, N- phenylaza- or benzocrown ether) with a chromophore so that both functional units share some critical atoms. The chromophore unit with an internal charge-transfer (ICT) excited state is used to produce a strong optical response to the cation−macrocycle interaction .…”

Section: Introductionmentioning

confidence: 99%

“…Crowned styryl compounds may show significant cation-induced changes in the absorption and/or fluorescence spectra. − However, most of them have rather low cation-binding ability and poor selectivity within the series of alkali or alkaline-earth metal cations. The introduction of the sulfo group into the N- alkyl substituent of 1 results in a considerable increase in the ability of the dye to bind alkaline-earth metal cations and photochemical control of the complex formation, but the cation-binding selectivity remains poor.…”

Section: Introductionmentioning

confidence: 99%

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Sandwich-Type Complexes of Alkaline-Earth Metal Cations with a Bisstyryl Dye Containing Two Crown Ether Units

et al. 1999

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The formation of complexes between a bisstyryl dye containing two benzo-15-crown-5 ether groups, 2, and Mg2+, Ca2+, Sr2+, and Ba2+ ions was studied in acetonitrile solution by using a spectrophotometric approach. In contrast to its monostyryl analogue 1, which shows a rather low cation-binding selectivity, the bisstyryl dye 2 selectively binds the Sr2+ and Ba2+ ions because of formation of intramolecular sandwich complexes. Alkaline-earth metal cations induce substantial blue shifts of the absorption maximum of 1 and 2, particularly in the case of sandwich complex formation. The emission behavior of 1 and 2 and their Ba2+ complexes in acetonitrile solution has also been studied. In both cases, complex formation leads to a blue shift of the fluorescence maximum and a decrease in the emission quantum yield. The fluorescence decay is monoexponential for the complex of 1 and biexponential for that of 2. The longer-lived fluorescence component, which corresponds to the lower-energy band in the steady-state spectrum, is assigned to an intramolecular excimer state.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Sandwich-Type Complexes of Alkaline-Earth Metal Cations with a Bisstyryl Dye Containing Two Crown Ether Units

et al. 1999

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“…By the careful design of the ionic binding unit conjugated with the styryl dye, some hemicyanine dye-based chemosensors have been recently developed that use ICT signaling mechanisms. For example, a styrylbenzothiazolium dye with a crown ether as a binding unit was developed for Mg 2+ [13], Ag + , Hg 2+ [14] and Ba 2+ [15] sensing. Boronic acid-grafted styryl pyridinium dyes have been used as cyanide fluorogenic chemosensors [16].…”

Section: Introductionmentioning

confidence: 99%

Novel styrylbenzothiazolium dye-based sensor for mercury, cyanide and hydroxide ions

Gwon

Rao

Kim

et al. 2015

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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“…Styryl dyes are known as heterocyclic organic molecules of the general formula R−Het + −CH=CH−ArX − can undergo E-Z photo-isomerization, electrocyclization and [2+2] Cycloaddition photoreactions owing to the presence of ethylene bonds in the dye molecules [1][2][3][4][5] . The photochemical properties of styryl dyes have been extensively studied [6][7][8][9][10][11][12] ; owing to their applications in several areas. These compounds were originally utilized as sensitizing additives to photographic emulsions and other additives in photographic industry, but their unique structural and photophysical characteristics have since proven useful for a wide variety of other applications requiring photosensitive materials, such as optical recording media and solar cells [13][14][15][16] .…”

Section: Introductionmentioning

confidence: 99%

Absorption, Fluorescence, Photochemical and Thermal cis/trans Isomerization Reactivity of 1-Methyl-4-(4ʹ-aminostyryl)pyridinium Iodide

2015

Chem Sci Trans

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The photo and thermal cis/trans isomerization reactions are studied for 1-methyl-4-(4 ʹaminostyryl)pyridinium iodide, Cy, which is prepared in the trans form. In a basic solution the trans form, Cy tr , cannot isomerise directly to the cis form. Its protonated form, Cy tr H + , is active and reacts photochemically from trans to cis configuration, Cy c H +. The quantum yields Ф tc and Ф ct are determined in water. Deprotonation process of Cy c H + yields the cis isomer, Cy c , which can thermally back to the stable trans form. The rate constants and the activated parameters of the thermal reaction are determined. Due to irreversibility of the thermal reaction, a complete molecular reaction cycle is performed in one direction. To get more information on the spectral characteristics of protonated form, the photochromic of the title compound is studied in different fourteen solvents. The linear relationships between absorption energy with hydrogen bond acceptor ability of the solvents and fluorescence energy of CyH + with free energy for transferring the proton to the solvent, DG t o were determined.

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Dependence of metal ion complexation and intermolecular aggregation on photoinduced geometric isomerism in a crown ether styryl dye

Cited by 63 publications

References 0 publications

Sandwich-Type Complexes of Alkaline-Earth Metal Cations with a Bisstyryl Dye Containing Two Crown Ether Units

Sandwich-Type Complexes of Alkaline-Earth Metal Cations with a Bisstyryl Dye Containing Two Crown Ether Units

Novel styrylbenzothiazolium dye-based sensor for mercury, cyanide and hydroxide ions

Absorption, Fluorescence, Photochemical and Thermal cis/trans Isomerization Reactivity of 1-Methyl-4-(4ʹ-aminostyryl)pyridinium Iodide

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