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Fullerene Dissymmetrization as a Means to Achieve Single Enantiomer Electron Acceptors with Maximized Chiroptical Responsiveness

preprint
submitted on 17.06.2020 and posted on 18.06.2020 by Wenda Shi, Francesco Salerno, Alejandro Santana-Bonilla, Matthew Ward, Xueyan Hou, John Dennis, Alasdair Campbell, Kim Jelfs, Matthew Fuchter

Solubilized fullerene derivatives have revolutionised 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. Here we separate 10 pairs of enantiomers from the 19 structural isomers of bis[60]PCBM, using them to elucidate important chiroptical structure-property relationships and demonstrating their application to a single enantiomer circularly polarized (CP) light detecting device. We find that larger chiroptical responses occur through inherent chirality of the fullerene cage and particularly through transitions with low CT character. When used in a single enantiomer organic field-effect transistor device, we demonstrate the potential to discriminate CP light with a fast light response time and with a very high photocurrent dissymmetry factor (gph = ±1.35). Our study thus provides key strategies to design fullerenes with large chiroptical responses for use as single enantiomer components of organic electronic devices. We anticipate that our data will position chiral fullerenes as an exciting material class for the growing field of chiral electronic technologies.

Funding

EPSRC Centre for Doctoral Training in Plastic Electronic Materials

Engineering and Physical Sciences Research Council

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FUNCTION THROUGH CHIRALITY IN ORGANIC ELECTRONIC MATERIALS AND DEVICES

Engineering and Physical Sciences Research Council

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ERC-StG-PE5-CoMMaD

History

Email Address of Submitting Author

m.fuchter@imperial.ac.uk

Institution

Imperial College London

Country

UK

ORCID For Submitting Author

0000-0002-1767-7072

Declaration of Conflict of Interest

No conflict of interest

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