Helical self-organization and hierarchical self-assembly of an oligoheterocyclic pyridine-pyridazine strand into extended supramolecular fibers.
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.
Cuccia
Louis A
LA
Laboratoire de Chimie Supramoléculaire ISIS, Université Louis Pasteur 4, rue Blaise Pascal, 67000 Strasbourg, France.
Ruiz
Eliseo
E
Lehn
Jean-Marie
JM
Homo
Jean-Claude
JC
Schmutz
Marc
M
D006571:Heterocyclic Compounds / Q000737:chemistry*; D008968:Molecular Conformation; D015394:Molecular Structure; D011724:Pyridazines / Q000737:chemistry*; D011725:Pyridines / Q000737:chemistry*; D012313:RNA / Q000737:chemistry
D006571:Heterocyclic Compounds; D011724:Pyridazines; D011725:Pyridines; D012313:RNA; C023666:pyridine