Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 2, Pages 752-757Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201912536
Keywords
cyclocarbonylation; fulvalenes; perylene diimides; radical anions; stability
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Funding
- National Natural Science Foundation of China (NSFC) [21790361, 21734009, 51673202]
- National Key R&D Program of China [2017YFA0204701]
- Youth Innovation Promotion Association of Chinese Academy of Sciences [2017048]
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The first example of a two-state (neutral and reduced), stable electron-accepting material and its radical anion is presented. FV-PDI, generated from cyclocarbonylation and then a carbonyl coupling reaction, shows a largely degenerate LUMO of -4.38 eV based on the delocalization of pi-electrons across the whole molecular skeleton through a fulvalene bridge. The stability and electron affinity allow spontaneous electron transfer to afford a stable radical anion. Spectroscopic characterization and structural elucidation showed that the radical anion [FV-PDI](.-) has remarkable stability and near-infrared absorptions extending to 1200 nm. Single-crystal X-ray diffraction analyses revealed significant changes in the molecular shape and packing arrangement of the formed radical anion. The central C-C bond linking the two PDI halves is lengthened from approximately 1.33 to 1.43 angstrom, and the alternating arrangement of positively and negatively charged units favor the stable charge-transfer complex.
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