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

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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 ( g ph = ±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.

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