Fullerene desymmetrization as a means to achieve single-enantiomer electron acceptors with maximized chiroptical responsiveness.
File(s)
Published version
Author(s)
Type
Journal Article
Abstract
Solubilized fullerene derivatives have revolutionized the development of organic photovoltaic devices, acting as excellent electron acceptors. The addition of solubilizing addends to the fullerene cage results in a large number of isomers, which are generally employed as isomeric mixtures. Moreover, a significant number of these isomers are chiral, which further adds to the isomeric complexity. The opportunities presented by single-isomer, and particularly single-enantiomer, fullerenes in organic electronic materials and devices are poorly understood however. Here, ten pairs of enantiomers are separated from the 19 structural isomers of bis[60]phenyl-C61-butyric acid methyl ester, using them to elucidate important chiroptical relationships and demonstrating their application to a circularly polarized light (CPL)-detecting device. Larger chiroptical responses are found, occurring through the inherent chirality of the fullerene. When used in a single-enantiomer organic field-effect transistor, the potential to discriminate CPL with a fast light response time and with a very high photocurrent dissymmetry factor (gph = 1.27 ± 0.06) is demonstrated. This study thus provides key strategies to design fullerenes with large chiroptical responses for use as chiral components of organic electronic devices. It is anticipated that this data will position chiral fullerenes as an exciting material class for the growing field of chiral electronic technologies.
Date Issued
2021-01-07
Date Acceptance
2020-11-01
Citation
Advanced Materials, 2021, 33 (1), pp.1-7
ISSN
0935-9648
Publisher
Wiley
Start Page
1
End Page
7
Journal / Book Title
Advanced Materials
Volume
33
Issue
1
Copyright Statement
© 2020 The Authors. Advanced Materials published by Wiley‐VCH GmbH
This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
License URL
Sponsor
Engineering & Physical Science Research Council (EPSRC)
Commission of the European Communities
The Royal Society
Identifier
https://www.ncbi.nlm.nih.gov/pubmed/33225503
Grant Number
EP/R00188X/1
758370
URF\R\180012
Subjects
chiral materials
chiroptical response
circularly polarized light
fullerenes
organic field-effect transistors
Publication Status
Published
Coverage Spatial
Germany
Date Publish Online
2020-11-23