Synthesis of stilbene analogues by one-pot oxidation-Wittig and oxidation-Wittig–Heck reaction
作者:Akeel S. Saiyed、Krupa N. Patel、Bola V. Kamath、Ashutosh V. Bedekar
DOI:10.1016/j.tetlet.2012.06.090
日期:2012.8
Synthesis of symmetrical (and unsymmetrical) stilbene derivatives is achieved by a combination of one-pot steps of Kornblum type oxidation of benzyl halide, its simultaneous in situ formation of phosphonium salt, and subsequently their Wittig reaction. In other variant it is oxidized to aldehyde, treated with ylide generated from phosphonium salt (CH3PPh3X) to give styrene, and subjected to Pd catalyzed
One-pot synthesis and study of spectroscopic properties of oligo(phenylenevinylene)s
作者:Krupa N. Patel、Ashutosh V. Bedekar
DOI:10.1016/j.tetlet.2015.10.033
日期:2015.11
Two series of OPVs (oligo(phenylenevinylene)), that is, ((1E,1'E)-(2,5-dimethoxy-1,4-phenylene)bis (ethene-2,1-diyl))dibenzene derivatives and 4-((E)-4-((E)-styryl)styryl)pyridine derivatives with different functional groups of varying electronic properties have been synthesized by one-pot Wittig-Heck methodology. The synthesized derivatives have been studied for their optical properties. Amongst them the ((1E,1'E)-(2,5-dimethoxy-1,4-phenylene)bis(ethene-2,1-diyl))dibenzene derivatives with appropriate changes in the end group showed a significant impact on the UV absorption and emission spectra. Particularly NO2-OPV showed distinct solvatochromism in the wavelength range of 218 nm in different solvents. Whereas 4-((E)-4((E)-styryl)styryl)pyridine derivatives showed clear acidochromism which can be detected visually as well as spectroscopically. (C) 2015 Elsevier Ltd. All rights reserved.
2,5-Bisvinyl-1,4-benzoquinones 1 and 2-vinyl-1,4-benzoquinones 2 substituted with aryl or ester end groups have been synthesized. The 2,5-bisstyryl-1,4-benzoquinones 1 (R=phenyl, p-tolyl, o-tolyl) crystallize with a 7 Angstrom-stacking axis. But only for the o-tolyl derivative the contacts between the vinyl groups are close enough to allow a four-center type photopolymerization. The ester derivative 1 (R=COOEt) has a layer structure and can be photooligomerized in the crystal. The generated cyclobutane subgroups have twofold symmetry. The vinylquinones 2 (R=aryl) may be dimerized photochemically in the crystal at the vinyl groups to centrosymmetric cyclobutanes. Crystals with 4 Angstrom stacking axis are also photoreactive.