A macrocyclic oligofuran: synthesis, solid state structure and electronic properties.
Chem Sci
; 10(37): 8527-8532, 2019 Oct 07.
Article
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| MEDLINE
| ID: mdl-32055302
ABSTRACT
We report the first π-conjugated macrocyclic system with an oligofuran backbone. The calculated HOMO-LUMO gap is similar to that of the corresponding linear polymer, indicating a remarkable electron delocalization. The X-ray structure reveals a planar conformation, in contrast to the twisted conformation of macrocyclic oligothiophenes. The intermolecular π-π stacking distance is extremely small (3.17 Å), indicating very strong interactions. The macrocycle forms large π-aggregates in solution and shows a tendency toward highly ordered multilayer adsorption at the solid-liquid interface. The face-on orientation of molecules explains the higher hole mobility observed in the out-of-plane direction.
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Chem Sci
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2019
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Article