Heterocyclic Annelated Di(perylene bisimide): Constructing Bowl-Shaped Perylene Bisimides by the Combination of Steric Congestion and Ring Strain

被引:61
作者
Qian, Hualei [2 ,3 ]
Yue, Wan [2 ,3 ]
Zhen, Yonggang [2 ,3 ]
Di Motta, Simone [1 ]
Di Donato, Eugenio [1 ]
Negri, Fabrizia [1 ]
Qu, Jianqiang [4 ]
Xu, Wei [2 ]
Zhu, Daoben [2 ]
Wang, Zhaohui [2 ]
机构
[1] Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy
[2] Chinese Acad Sci, Beijing Natl Lab Mol Sci, Key Lab Organ Solids, Inst Chem, Beijing 100864, Peoples R China
[3] Chinese Acad Sci, Grad Sch, Beijing 100190, Peoples R China
[4] BASF AG, D-67056 Ludwigshafen, Germany
基金
中国国家自然科学基金;
关键词
MOLECULAR ASSEMBLY CODES; THIN-FILM TRANSISTORS; ORGANIC SEMICONDUCTORS; HIGH-MOBILITY; DYES; DERIVATIVES; ENERGY; REHYBRIDIZATION; HYDROCARBONS; ELECTRONICS;
D O I
10.1021/jo901285k
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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 H-1 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 structure, electronic properties, and optical signatures were computed with density functional theory.
引用
收藏
页码:6275 / 6282
页数:8
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