Supramolecular organic photochemistry of crown-ether-containing styryl dyes

Gromov, S. P.; Алфимов, М. В.

doi:10.1007/bf02495186

Cited by 60 publications

(41 citation statements)

References 22 publications

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“…This type of photoreaction has been observed for all crown containing styryl dyes stud ied earlier. 3 The formation of the Z isomer of dye 1 was proved by studying the 1 H NMR spectra of a photostationary mix ture. The assignment of the signals is shown in Fig.…”

Section: Synthesis and Spectroscopic Studiesmentioning

confidence: 99%

Stereospecific solid-state [2+2] autophotocycloaddition of a styryl dye containing a 18-crown-6 fragment

et al. 2005

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A procedure was developed for the synthesis of a 18 crown 6 containing styryl dye of the pyridine series. Phototransformation products of the dye that formed upon irradiation with visible light in solution, films, and crystals were studied by 1 H and 13 C NMR spectroscopy and spectrophotometry. Irradiation of solutions of this dye in acetonitrile leads only to reversible E-Z photoisomerization of the C=C bond. Irradiation of a film of the dye induces stereospe cific [2+2] photocycloaddition to form exclusively the rctt isomer of tetrasubstituted cyclobutane. The latter was found to undergo base catalyzed isomerization giving rise to the rcct isomer. X ray diffraction study showed that photocycloaddition occurs in single crystals without their destruction. The structures of the E isomer of the dye and the resulting rctt isomer of the cyclobutane derivative were established. The characteristic features of the molecular packing of the dye favorable for topochemical photocycloaddition in the crystal and the structural changes that accompany the cyclobutane formation are discussed.

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Section: Synthesis and Spectroscopic Studiesmentioning

confidence: 99%

Stereospecific solid-state [2+2] autophotocycloaddition of a styryl dye containing a 18-crown-6 fragment

et al. 2005

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“…± Crown compounds containing a chromophore conjugated with the macrocycle serve as selective photosensitive complexones for metal cations [1] [2]. It was shown previously that crown-containing styryl dyes (CSD), in particular dye I [3], bind metal ions and that complex formation changes the spectral and photochemical characteristics of the dyes. Dyes of this type have been used for the development of novel photochemical and photophysical molecular devices [4 ± 7].…”

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Synthesis, Structure, Spectroscopic Studies, and Complexation of Novel Crown Ether Butadienyl Dyes

Gromov¹,

Ведерников²,

Ushakov³

et al. 2002

HCA

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Dedicated to Professor Andre¬ M. Braun on the occasion of his 60th birthday Butadienyl dyes of the benzothiazole series with various fragments of benzocrown ethers 1a ± c were synthesized for the first time. The structures and spectral properties of crown-containing butadienyl dyes and their complexes with alkali and alkaline-earth metal cations were studied by X-ray diffraction analysis and 1 H-NMR, UV/VIS, and resonance Raman spectroscopy. To interpret the experimental results, quantumchemical calculations were performed. In the case of Sr 2 and Ba 2 ions, the formation of strong sandwich complexes [M(1b) 2 ] 2 of an unusual structure involving stacking interactions was established; the dye molecules are arranged one above another in the complex according to the −head-to-head× pattern.

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“…[5][6][7][8][9][10][11] Compounds 3 and 4 are representatives of the crown-containing styryl dyes that show negative ionochromism. [6,7] The N-methylazacrown fragment in 4 proved to be better preorganized for binding of metal ions than the N-phenylazacrown fragment in 3.…”

Section: Donor-acceptor Chromoionophoresmentioning

confidence: 99%

Crown Ether Based Optical Molecular Sensors and Photocontrolled Ionophores

Ushakov¹,

Алфимов²,

Gromov³

2010

MHC

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Supramolecular organic photochemistry of crown-ether-containing styryl dyes

Abstract: The data on the molecular design, spectral properties, photochemistry and complexation of photochromic crown ethers containing a C=C bond are described systematically and generalized. Prospects for the practical application of these compounds are considered.

Cited by 60 publications

References 22 publications

Stereospecific solid-state [2+2] autophotocycloaddition of a styryl dye containing a 18-crown-6 fragment

Stereospecific solid-state [2+2] autophotocycloaddition of a styryl dye containing a 18-crown-6 fragment

Synthesis, Structure, Spectroscopic Studies, and Complexation of Novel Crown Ether Butadienyl Dyes

Crown Ether Based Optical Molecular Sensors and Photocontrolled Ionophores

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