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Fullerene Desymmetrization as a Means to Achieve Single‐Enantiomer Electron Acceptors with Maximized Chiroptical Responsiveness
Author(s) -
Shi Wenda,
Salerno Francesco,
Ward Matthew D.,
SantanaBonilla Alejandro,
Wade Jessica,
Hou Xueyan,
Liu Tong,
Dennis T. John S.,
Campbell Alasdair J.,
Jelfs Kim E.,
Fuchter Matthew J.
Publication year - 2021
Publication title -
advanced materials
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 10.707
H-Index - 527
eISSN - 1521-4095
pISSN - 0935-9648
DOI - 10.1002/adma.202004115
Subject(s) - fullerene , enantiomer , chirality (physics) , materials science , organic solar cell , desymmetrization , photocurrent , electron acceptor , combinatorial chemistry , chemical physics , computational chemistry , nanotechnology , organic chemistry , enantioselective synthesis , optoelectronics , chemistry , polymer , chiral symmetry breaking , physics , catalysis , quantum mechanics , nambu–jona lasinio model , composite material , quark
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 ( g ph = 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.