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Issue 37, 2019

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

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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.

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

Supplementary files

Article information


Submitted
02 Jul 2019
Accepted
19 Aug 2019
First published
19 Aug 2019

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2019,10, 8527-8532
Article type
Edge Article

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

S. V. Mulay, O. Dishi, Y. Fang, M. R. Niazi, L. J. W. Shimon, D. F. Perepichka and O. Gidron, Chem. Sci., 2019, 10, 8527 DOI: 10.1039/C9SC03247A

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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