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Bowl-Shaped Bispyrrole-Fused Perylene-diimide and Its Anions
Organic Letters ( IF 4.9 ) Pub Date : 2023-01-05 , DOI: 10.1021/acs.orglett.2c04220
Xinyue Tian 1 , Yao Xiao 1 , Shuoyingjie Wang 1 , Guanghua Liu 1 , Wenhao Zhang 1 , Laiyun Zhou 1 , Jianye Gong 1 , Xuejin Zhang 1 , Xiang Li 2 , He Meng 1 , Jianguo Wang 1 , Gaole Dai 3 , Qing Wang 1
Affiliation  

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.

中文翻译:

碗状双吡咯稠合苝二亚胺及其阴离子

自 2009 年以来,在苝二酰亚胺的海湾位置并入两个吡咯亚基一直是一个长期追求的目标,但由于高应变而未能实现。在此,通过一步 Buchwald-Hartwig 反应,成功生成碗深度为 1.52 Å 的PDI-2N 。通过富电子吡咯包埋,PDI-2N的自由基阴离子和二价阴离子很容易制备,并进行了实验和理论研究。此外,PDI-2N在不同条件下以不同方式结晶,在DMF条件下形成无限双向柱状堆叠的管状晶体。这一发现开发了一种梦幻般的碗状 PDI 衍生物,在有机电子学中具有广阔的应用前景。
更新日期:2023-01-05
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