Oligo(p-phenylenevinylene) peptide conjugates: Synthesis and self-assembly in solution and at the solid-liquid interface

R. Matmour, I. Cat, de, S.J. George, W. Adriaens, P.E.L.G. Leclère, P.H.H. Bomans, N.A.J.M. Sommerdijk, J.C. Gielen, P.C.M. Christianen, J.T. Heldens, J.C.M. van Hest, D.W.P.M. Lowik, S. Feyter, de, E.W. Meijer, A.P.H.J. Schenning

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Abstract

Two oligo(p-phenylenevinylene)-peptide hybrid amphiphiles have been synthesized using solid-and liquid-phase strategies. The amphiliphiles are composed of a Ï€-conjugated oligo(p-phenylenevinylene) trimer (OPV) which is coupled at either a glycinyl-alanyl-glycinyl-alanyl-glycine (GAGAG) silk-inspired +Ý-sheet or a glycinyl-alanyl-asparagyl-prolyl-asparagy- alanyl-alanyl-glycine (GANPNAAG) +Ý-turn forming oligopeptide sequence. The solid-phase strategy enables one to use longer peptides if strong acidic conditions are avoided, whereas the solution-phase coupling gives better yields. The study of the two-dimensional (2D) self-assembly of OPV-GAGAG by scanning tunneling microscopy (STM) at the submolecular level demonstrated the formation of bilayers in which the molecules are lying antiparallel in a +Ý-sheet conformation. In the case of OPV-GANPNAAG self-assembled monolayers could not be observed. Absorption, fluorescence, and circular dichroism studies showed that OPV-GAGAG and OPV-GANPNAAG are aggregated in a variety of organic solvents. In water cryogenic temperature transmission electron microscopy (cryo-TEM), atomic force microscopy (AFM), light scattering, and optical studies reveal that self-assembled nanofibers are formed in which the helical organization of the OPV segments is dictated by the peptide sequence. -© 2008 American Chemical Society
Original languageEnglish
Pages (from-to)14576-14583
JournalJournal of the American Chemical Society
Volume130
Issue number44
DOIs
Publication statusPublished - 2008

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