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 singlecrystal X-ray structure analysis and temperature-dependent 1H 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, 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.

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

DI MOTTA, SIMONE;NEGRI, FABRIZIA;
2009

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 singlecrystal X-ray structure analysis and temperature-dependent 1H 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, 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.
2009
H. Qian; W. Yue; Y. Zhen; S. Di Motta; E. Di Donato; F. Negri; J. Qu; W. Xu; D. Zhu; Z. Wang
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11585/77426
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