DNA-assisted self-assembly of pyrene foldamers.
ABSTRACT The self-organization of oligopyrene foldamers is described. Bi- and tri-segmental oligomers composed of nucleotides and non-nucleosidic, achiral pyrene monomers form double-stranded helical structures, as shown by absorbance, fluorescence, and CD spectroscopy. The mixed nature of alternating aromatic and phosphate groups ensures water solubility which, in turn, favors folding of the aromatic units. Pyrene molecules also assemble though interstrand stacking interactions. Structural organization of the pyrene units is an intrinsic property of the oligoaryl part and takes place independently from the sequence of the attached DNA. Chirality transfer from DNA to the pyrene segment leads to formation of a double helix, in which neighboring pyrene units are, in the present case, twisted in a right-handed manner. Pyrene helicity is most pronounced in a bi-segmental chimera, in which a DNA stem is present only at one end of the pyrene section.
- Chemical Reviews 12/2001; 101(11):3457-97. · 41.30 Impact Factor
Article: The chain-length dependence test.[show abstract] [hide abstract]
ABSTRACT: Trends obtained from systematic studies based on chain-length variation have provided valuable insight and understanding into the behavior of m-phenylene ethynylene foldamers. The generalization of this experimental approach, the chain-length dependence test, is useful for studying solution conformation, packing in the solid state, specific intrachain interactions, and the contributions of end groups to a particular property.Accounts of Chemical Research 02/2006; 39(1):11-20. · 20.83 Impact Factor
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ABSTRACT: Pyrene excimer fluorescence is effectively quenched by non-nucleosidic perylene diimides upon DNA duplex formation.Chemical Communications 06/2008; · 6.38 Impact Factor