Dicyclohepta[ijkl,uvwx]rubicene with Two Pentagons and Two Heptagons as a Stable and Planar Non-benzenoid Nanographene |
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Authors: | Dr Xi-Sha Zhang Yan-Ying Huang Jing Zhang Dr Wei Meng Dr Qian Peng Ruirui Kong Zhenwei Xiao Dr Jie Liu Miaofei Huang Dr Yuanping Yi Liangliang Chen Qingrui Fan Dr Gaobo Lin Dr Zitong Liu Dr Guanxin Zhang Dr Lang Jiang Prof Dr Deqing Zhang |
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Institution: | 1. Beijing National Laboratory for Molecular Sciences, Organic Solids Laboratory, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190 China;2. Beijing National Laboratory for Molecular Sciences, Organic Solids Laboratory, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190 China
School of Chemical Sciences, University of Chinese Academy of Sciences, Beijing, 100049 China |
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Abstract: | Polycyclic aromatic hydrocarbons with hexagons/pentagons or hexagons/heptagons have been intensively investigated in recent years, but those with simultaneous presence of hexagons, pentagons and heptagons remain rare. In this paper, we report dicycloheptaijkl,uvwx]rubicene ( DHR ), a non-benzenoid isomer of dibenzobc,kl]coronene with two pentagons and two heptagons. We developed an efficient and scalable synthetic method for DHR by using Scholl reaction and dehydrogenation. Crystal structure of DHR shows that the benzenoid rings, two pentagons and two heptagons are coplanar. The bond lengths analysis and the ICSS(1)zz and LOL-π calculations indicate that the incorporation of two formal azulene moieties has an effect on the conjugated structure. The π-electrons of benzenoid and pentagon rings are more delocalized. Cyclic voltammetry studies indicate that DHR shows multiple oxidation and reduction potentials. Interestingly, DHR exhibits unusual S0 to S2 absorption and abnormal anti-Kasha S2 to S0 emission. Moreover, crystals of DHR exhibit semiconducting behaviour with hole mobility up to 0.082 cm2 V−1 s−1. |
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Keywords: | Azulen Dicycloheptarubicen Nanographen Organische Halbleiter Scholl-Reaktion |
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