Related Experiment Video
Updated: Jun 24, 2026

Self-assembling Morphologies Obtained from Helical Polycarbodiimide Copolymers and Their Triazole Derivatives
Published on: February 7, 2017
Photodimerization processes in self-assembled chiral oligo(p-phenylenevinylene) bolaamphiphiles
Subi J George1,2, Tom F A de Greef1, Ralf Bovee1
1Laboratory for Macromolecular and Organic Chemistry, Eindhoven University of Technology, PO Box 513, NL-5600MB Eindhoven (The Netherlands), Fax: (+31) 40-2451036.
Abstract:
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.
Related Concept Videos
Photochemical Electrocyclic Reactions: Stereochemistry
Selection Rules: Photochemical Activation
Cationic Chain-Growth Polymerization: Mechanism
Cycloaddition Reactions: MO Requirements for Photochemical Activation
Preparation of Diols and Pinacol Rearrangement
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.
Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)
Anionic Chain-Growth Polymerization: Mechanism

