A macrocyclic oligofuran: synthesis, solid state structure and electronic properties. Issue 37 (27th August 2019)

• Record Type: Journal Article
• Authors: Mulay, Sandip V.; Dishi, Or; Fang, Yuan; Niazi, Muhammad R.; Shimon, Linda J. W.; Perepichka, Dmitrii F.; Gidron, Ori
• Is Part Of: Chemical science. Volume 10:Issue 37(2019)
• Page Start: 8527
• Page End: 8532
• Publication Date: 2019-08-27
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/c9sc03247a
• Languages: English
• ISSNs: 2041-6520

Abstract

Abstract : The first π-conjugated macrocyclic system with an oligofuran backbone display planar conformation and forms large π-aggregates, in contrast to the twisted conformation of small macrocyclic oligothiophenes. 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.