Renatus Sinkeldam - Chiral Alignment of OPV Chromophores: Exploitation of the Ureidophthalimide Based Foldamer.

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      R. W. Sinkeldam, F. J. M. Hoeben, M. J. Pouderoijen, I. De Cat,   J. Zhang, S. Furukawa, S. De Feyter, J. A. J. M. Vekemans, and E.   W. Meijer, J. Am. Chem. Soc. 2006,   128, 16113-21.


      The ability of foldamers to adopt a secondary structure in   solution has been exploited to organize peripheral functionality.   Our previously reported poly(ureidophthalimide) foldamer proved   to be an excellent scaffold for the chiral organization of   peripherally positioned oligo(p-phenylenevinylene) (OPV)   chromophores. Facile high-yielding synthesis gave access to the   required OPV-decorated building blocks. A condensation   polymerization provided polymers of sufficient length to allow   construction of a helical architecture comprising several turns.   Short and long chains were separated by chromatography. Circular   dichroism studies in THF of the longer chains indicate the   presence of helically arranged OPVs. However, such an effect is   not observed in CHCl3. Remarkable are the measurements   of the OPV foldamers in heptane. A bisignate Cotton effect is   observed in heptane of a sample with a THF history. No Cotton   effect is observed in heptane of a sample with a CHCl3  history. In this example of supramolecular synthesis, the solvent   dictates the expression of supramolecular chirality in a   secondary structure. The short-chain oligomeric fractions that   are unable to create a full turn revealed on scanning tunneling   microscopy analysis the presence of circular architectures at the   graphite/1-phenyloctane interface. This is in full agreement with   the proposed conformation of the decorated foldamers.

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