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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
Vise andre og tillknytning
2003 (engelsk)Inngår i: The Journal of Organic Chemistry, Vol. 68, nr 16, s. 6115-25Artikkel i tidsskrift (Fagfellevurdert) Published
Abstract [en]

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.

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2003. Vol. 68, nr 16, s. 6115-25
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URN: urn:nbn:se:umu:diva-10056DOI: 10.1021/jo034460xScopus ID: 2-s2.0-0041530007OAI: oai:DiVA.org:umu-10056DiVA, id: diva2:149727
Tilgjengelig fra: 2008-06-12 Laget: 2008-06-12 Sist oppdatert: 2023-03-23bibliografisk kontrollert

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