title: Heterocyclic annelated di(perylene bisimide): constructing bowl-shaped perylene bisimides by the combination of steric congestion and ring strain.
abstract: In this paper, we present the synthesis of S- and N-heterocyclic annelated di(perylene bisimide) with extraordinary doubly bowl-shaped structures. The structures of fused PBI bowls confirmed by single-crystal X-ray structure analysis and temperature-dependent (1)H NMR are realized by the introduction of the steric congestion in nonbay regions and by the concurrent formation of the five-membered heterorings strain in bay regions. On the basis of the geometry obtained from the X-ray analysis, the maximum POAV1 pyramidalization angle is found in N-heterocyclic annelated diPBI 7, as large as 4.7 degrees , indicating the formation of two PBI bowls with significant curvatures. Furthermore, to assist the electrochemical and spectroscopic characterization of the two bowl-shaped derivatives and to assess the influence of heteroatoms on the bowl curvature, quantum-chemically optimized atomic structures, electronic properties, and optical signatures were computed with density functional theory.
authors: Beijing National Laboratory for Molecular Sciences, Key Laboratory of Organic Solids, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China.
authors: Hualei
authors: H
authors: Qian
authors: Wan
authors: W
authors: Yue
authors: Yonggang
authors: Y
authors: Zhen
authors: Simone
authors: S
authors: Di Motta
authors: Eugenio
authors: E
authors: Di Donato
authors: Fabrizia
authors: F
authors: Negri
authors: Jianqiang
authors: J
authors: Qu
authors: Wei
authors: W
authors: Xu
authors: Daoben
authors: D
authors: Zhu
authors: Zhaohui
authors: Z
authors: Wang