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- Title
Syntheses, structures, and supramolecular properties of giant π-expanded macrocyclic oligothiophenes.
- Authors
Iyoda, Masahiko
- Abstract
Fully conjugated π-expanded macrocyclic oligothiophenes with 60π-, 90π-, 120π-, 150π-, and 180π-electron systems ( 1- 5) were synthesized using modified McMurry coupling reaction as a key step. Compound 1 was converted into macrocyclic oligo(2,5-thienylene-ethynylene) 6 using bromination-dehydrobromination procedure. X-ray analysis of 1 revealed a unique molecular and packing structure, reflecting a round, planar shape with nanoscale inner cavity. Interestingly, 2 and 3 self-aggregate in the solid state to form nanowires. The structure of fibrous aggregates was established by scanning electron microscopic and atomic force microscopic analyses. Compounds 1- 6 exhibit multi-step reversible redox behavior with fairly low first oxidation potentials, reflecting their cyclic conjugation. Doping of 1- 3 with iodine gives semiconductors owing to their π-donor properties and π-π stacking ability. © 2007 Wiley Periodicals, Inc. 18:460-466, 2007; Published online in Wiley InterScience (). DOI 10.1002/hc.20337
- Publication
Heteroatom Chemistry, 2007, Vol 18, Issue 5, p460
- ISSN
1042-7163
- Publication type
Other
- DOI
10.1002/hc.20337