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Novel Photoswitchab...
Novel Photoswitchable Receptors: Synthesis and Cation-Induced Self-Assembly into Dimeric Complexes Leading to Stereospecific [2+2]-Photocycloaddition of Styryl Dyes Containing a 15-Crown-5 Ether Unit
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Gromov, Sergey P (author)
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Ushakov, Evgeny N (author)
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Fedorova, Olga A (author)
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Baskin, Igor I (author)
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Buevich, Alexei V (author)
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Andryukhina, Elena N (author)
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Alfimov, Michael V (author)
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- Johnels, Dan (author)
- Umeå universitet,Kemiska institutionen
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- Edlund, Ulf (author)
- Umeå universitet,Kemiska institutionen
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Whitesell, James K (author)
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Fox, Marye Anne (author)
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(creator_code:org_t)
- 2003-06-27
- 2003
- English.
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In: The Journal of Organic Chemistry. - : American Chemical Society (ACS). - 0022-3263 .- 1520-6904. ; 68:16, s. 6115-25
- Related links:
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https://urn.kb.se/re...
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https://doi.org/10.1...
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Abstract
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- Styryl dyes 4a-e containing a 15-crown-5 ether unit and a quinoline residue with a sulfonatoalkyl or sulfonatobenzyl N-substituent were synthesized. The relationship between the photochemical behavior of these dyes and their aggregates derived from complexation with Mg2+ in MeCN was studied using 1H NMR and absorption spectroscopy. The E-isomers of 4a-e were shown to form highly stable dimeric (2:2) complexes with Mg2+. Upon irradiation with visible light, the dimeric complexes undergo two competing photoreactions, viz., geometric E Z isomerization, resulting in an anion-capped 1:1 complex of the Z-isomer with Mg2+ and stereospecific syn-head-to-tail [2+2]-cycloaddition, affording a single isomer of bis-crown-containing cyclobutane. The N-substituent in the dye has a dramatic effect on the photochemical behavior of the dimeric complex. Molecular dynamics and semiempirical quantum-chemical calculations were carried out to interpret the observed photocycloaddition in the dimer. Conformational equilibria for the dimer of (E)-4b were analyzed using 1H NMR spectroscopy.
Subject headings
- NATURVETENSKAP -- Kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences (hsv//eng)
Publication and Content Type
- ref (subject category)
- art (subject category)
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- By the author/editor
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Gromov, Sergey P
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Ushakov, Evgeny ...
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Fedorova, Olga A
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Baskin, Igor I
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Buevich, Alexei ...
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Andryukhina, Ele ...
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show more...
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Alfimov, Michael ...
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Johnels, Dan
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Edlund, Ulf
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Whitesell, James ...
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Fox, Marye Anne
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show less...
- About the subject
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- NATURAL SCIENCES
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NATURAL SCIENCES
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and Chemical Science ...
- Articles in the publication
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The Journal of O ...
- By the university
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Umeå University