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Helical Self‐Organization and Hierarchical Self‐Assembly of an Oligoheterocyclic Pyridine–Pyridazine Strand into Extended Supramolecular Fibers
Author(s) -
Cuccia Louis A.,
Lehn JeanMarie,
Homo JeanClaude,
Schmutz Marc
Publication year - 2002
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/1521-3765(20020802)8:15<3448::aid-chem3448>3.0.co;2-#
Subject(s) - supramolecular chemistry , pyridazine , self assembly , pyridine , materials science , chemistry , polymer chemistry , nanotechnology , crystallography , stereochemistry , organic chemistry , crystal structure
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.