Photodimerization processes in self-assembled chiral oligo(p-phenylenevinylene) bolaamphiphiles.
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.
George
Subi J
SJ
Laboratory for Macromolecular and Organic Chemistry, Eindhoven University of Technology, PO Box 513, NL-5600MB Eindhoven (The Netherlands), Fax: (+31) 40-2451036.|New Chemistry Unit, Jawaharlal Nehru Centre for Advanced scientific Research (JNCASR), Jakkur, Bangalore, India-560064 (India).
de Greef
Tom F A
TFA
Laboratory for Macromolecular and Organic Chemistry, Eindhoven University of Technology, PO Box 513, NL-5600MB Eindhoven (The Netherlands), Fax: (+31) 40-2451036.
Bovee
Ralf
R
Laboratory for Macromolecular and Organic Chemistry, Eindhoven University of Technology, PO Box 513, NL-5600MB Eindhoven (The Netherlands), Fax: (+31) 40-2451036.
van Dongen
Joost L J
JLJ
Laboratory for Macromolecular and Organic Chemistry, Eindhoven University of Technology, PO Box 513, NL-5600MB Eindhoven (The Netherlands), Fax: (+31) 40-2451036.
Schenning
Albertus P H J
APHJ
Laboratory for Macromolecular and Organic Chemistry, Eindhoven University of Technology, PO Box 513, NL-5600MB Eindhoven (The Netherlands), Fax: (+31) 40-2451036.
Meijer
E W
EW
Laboratory for Macromolecular and Organic Chemistry, Eindhoven University of Technology, PO Box 513, NL-5600MB Eindhoven (The Netherlands), Fax: (+31) 40-2451036.