期刊
CHEMISTRY-AN ASIAN JOURNAL
卷 4, 期 6, 页码 910-917出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/asia.200900031
关键词
amphiphiles; conjugation; dimerization; photochemistry; self-assembly
资金
- Council for Chemical Sciences of the Netherlands Organization for Scientific Research (CW-NWO)
- EURYI
An oligo(p-phenylene vinylene) (OPV) amphiphile has been synthesized with a positively charged head group on one end and a hydrophilic ethyleneglycol wedge on the other. In water, this bolaamphiphile forms vesicles consisting of a monolayer in which the OPV surfactants are organized in a helical head-to-tail fashion. Mass spectrometry analysis and reversed-phase high performance liquid chromatography (RP-HPLC) reveals that because of the presence of two double bonds in the OPV units, photo-induced [2+2] cycloaddition takes place resulting in polymerization of the surfactants. Performing RP-HPLC allowed the OPV dimer to be isolated in a sufficient amount to perform a variety of one- and two-dimensional NMR experiments. These experiments show a highly stereoselective photochemical cycloaddition process resulting in a regioselective head-to-tail dimerization with a stereoselective syn arrangement.
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