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

Sandip V. Mulay, Or Dishi, Yuan Fang, Muhammad R. Niazi, Linda J.W. Shimon, Dmitrii F. Perepichka*, Ori Gidron

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

21 Scopus citations

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.

Original languageAmerican English
Pages (from-to)8527-8532
Number of pages6
JournalChemical Science
Volume10
Issue number37
DOIs
StatePublished - 2019

Bibliographical note

Publisher Copyright:
© 2019 The Royal Society of Chemistry.

Fingerprint

Dive into the research topics of 'A macrocyclic oligofuran: Synthesis, solid state structure and electronic properties'. Together they form a unique fingerprint.

Cite this