Dynamic chirality, chirality transfer and aggregation behaviour of dithienylethene switches

Tetrahedron

Volumn 64, Issue 36, 2008, Pages 8324-8335

  de Jong, Jaap J D ^a   van Rijn, Patrick ^a   Tiemersma Wegeman, Theodora D ^a   Lucas, Linda N ^a   Browne, Wesley R ^a   Kellogg, Richard M ^b   Uchida, Kingo ^c   van Esch, Jan H ^a   Feringa, Ben L ^a  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

^b Syncom BV   (Netherlands)

^c RYUKOKU UNIVERSITY   (Japan)

Author keywords

Amide gel; Diarylethene; Photochromic switching; Supramolecular

Indexed keywords

AMIDE; DITHIENYLETHENE; ETHYLENE DERIVATIVE; SOLVENT;

ARTICLE; CHEMICAL ANALYSIS; CHIRALITY; GELATION; HYDROGEN BOND; MOLECULAR DYNAMICS; MOLECULAR INTERACTION; PRIORITY JOURNAL; STEREOCHEMISTRY; SUPRAMOLECULAR CHEMISTRY; SYNTHESIS;

EID: 47949118734     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.05.129     Document Type: Article

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31. For electrochemical properties compounds 1-13 show very similar behavior. For all compounds in the open state an irreversible wave at 1.29 (3) V (vs SCE) was observed, which did not result in switching to the closed form, with the exception of 11o, where the oxidation falls outside the potential window of methanol. In the closed state all compounds, including 11c, show a quasi reversible oxidation at 0.74 (2) V (vs SCE) and an irreversible oxidation at 0.83 (2) V (vs SCE).
32. 30-120 s after cooling to rt, and even faster by quenching in either ice-water (0 °C), cold methanol (-40 °C) or even liquid nitrogen (-192 °C).
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34. The zero point crossing on the y-axis is obsecured by the solvent absorption, but extrapolation of the lines point to a common CD minimum at λ=297 nm.
35. All samples were prepared similarly, although at different minimal gelation concentrations according to Table 1. The concentrations needed for gelation of 2o in benzene, tetralin, 1,4-dioxane and butylacetate are too high to allow for measurement of CD spectra.
36. As for 1o, the zero point crossing on the y-axis is obsecured by the solvent absorption for 2o, but extrapolation of the lines point to a common CD minimum at λ=295 nm.
37. 1 and in hot toluene showed racemic 3c with signals for the thiophene proton matching those of the gels.
38. For the spectrum of 1o in toluene see Ref. 5c.
39. The absorbance between 325-380 nm is close to the limit of the dynamic range of the spectrophotometer; the unusual shape of the CD signal for gel β 2c is due to the high absorbance.
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