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A macrocyclic oligofuran: synthesis, solid state structure and electronic properties.

ABSTRACT: We report the first ?-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 ?-? stacking distance is extremely small (3.17 Å), indicating very strong interactions. The macrocycle forms large ?-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.

SUBMITTER: Mulay SV

PROVIDER: S-EPMC7003964 | biostudies-literature | 2019 Oct

REPOSITORIES: biostudies-literature

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A macrocyclic oligofuran: synthesis, solid state structure and electronic properties.

Mulay Sandip V SV Dishi Or O Fang Yuan Y Niazi Muhammad R MR Shimon Linda J W LJW Perepichka Dmitrii F DF Gidron Ori O

Chemical science 20190819 37

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 ...[more]

PMID: 32055302

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