Helical self-organization and hierarchical self-assembly of an oligoheterocyclic pyridine-pyridazine strand into extended supramolecular fibers

Chemistry. 2002 Aug 2;8(15):3448-57. doi: 10.1002/1521-3765(20020802)8:15<3448::AID-CHEM3448>3.0.CO;2-#.

Abstract

The synthesis and characterization of an alternating pyridine-pyridazine strand comprising thirteen heterocycles are described. Spontaneous folding into a helical secondary structure is based on a general molecular self-organization process enforced by the conformational information encoded within the primary structure of the molecular strand itself. Conformational control based on heterocyclic "helicity codons" illustrates a strategy for designing folding properties into synthetic oligomers (foldamers). Strong intermolecular interactions of the highly ordered lock-washer subunits of compound 3 results in hierarchical supramolecular self-assembly into protofibrils and fibrils. Compound 3 also forms mechanically stable two-dimensional Langmuir-Blodgett and cast thin films.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Heterocyclic Compounds / chemistry*
  • Molecular Conformation
  • Molecular Structure
  • Pyridazines / chemistry*
  • Pyridines / chemistry*
  • RNA / chemistry

Substances

  • Heterocyclic Compounds
  • Pyridazines
  • Pyridines
  • RNA
  • pyridine