Bowl-Shaped Bispyrrole-Fused Perylene-diimide and
Its Anions

Tian, Xinyue; Xiao, Yao; Wang, Shuoyingjie; Liu, Guanghua; Zhang, Wenhao; Zhou, Laiyun; Gong, Jianye; Zhang, Xuejin; Li, Xiang; Meng, He; Wang, Jianguo; Dai, Gaole; Wang, Qing

doi:10.1021/acs.orglett.2c04220.s001

Bowl-Shaped Bispyrrole-Fused Perylene-diimide and Its Anions

https://doi.org/10.1021/acs.orglett.2c04220.s001
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journal contribution

posted on 2023-01-05, 14:12 authored by Xinyue Tian, Yao Xiao, Shuoyingjie Wang, Guanghua Liu, Wenhao Zhang, Laiyun Zhou, Jianye Gong, Xuejin Zhang, Xiang Li, He Meng, Jianguo Wang, Gaole Dai, Qing Wang

Incorporating two pyrrole subunits at the bay positions of perylene-diimide has been a long-pursued goal since 2009, but it has not been achieved due to high strain. Herein, via one step Buchwald–Hartwig reaction, PDI-2N was successfully generated with a bowl depth of 1.52 Å. Though with electron-rich pyrrole embedding, PDI-2N’s radical anion and dianion were facilely prepared and were investigated both experimentally and theoretically. Moreover, PDI-2N crystallized in different manners under distinct conditions, and it formed tubular crystals with infinite two-directional columnar stacking under DMF conditions. This finding develops a dream bowl-shaped PDI derivative that holds great promise in organoelectronics.