Tang Zefeng, Li Tianyu, Cao Yucai, Zhang Yuyan, He Lifei, Zheng Aibin, Lei Ming
Department of Chemistry, Zhejiang University, Hangzhou, 310027, P. R. China.
State key laboratory of Polyolefins and Catalysis, Shanghai Key Laboratory of Catalysis Technology for Polyolefins, Shanghai Research Institute of Chemical Industry Co. Ltd, Shanghai, P. R. China.
ChemSusChem. 2021 Nov 19;14(22):4923-4928. doi: 10.1002/cssc.202101551. Epub 2021 Oct 12.
Chrysene is a readily available material for exploring new polycyclic aromatic hydrocarbons (PAHs). In this study, two chrysene based azahelicenes, nine-membered BA7 and ten-membered DA6, are constructed by intermolecular oxidative annulation of 6-aminochrysene and intramolecular annulation of N ,N -bis(1-chloronaphthalen-2-yl)chrysene-6,12-diamine, respectively. The hexylated BA7 and DA6 and their brominated products were undoubtedly characterized by single crystal XRD. Subsequent amination with bis(9-methyl-9H-carbazol-3-yl)amine (BMCA) electron donor afforded D-π-D-type semiconductors BA7-BMCA and DA6-BMCA with beneficial properties to act as hole transport materials for perovskite solar cell. Compared with 19.4 % champion power conversion efficiency (PCE) of BA7-BMCA based device, a higher PCE of 20.2 % for DA6-BMCA counterpart may be attributed to its S-shaped double helicene-like linker with extended π-conjugated system.
苊是一种易于获取的用于探索新型多环芳烃(PAHs)的材料。在本研究中,通过6-氨基苊的分子间氧化环化反应和N,N-双(1-氯萘-2-基)苊-6,12-二胺的分子内环化反应,分别构建了两种基于苊的氮杂螺旋烯,九元环的BA7和十元环的DA6。己基化的BA7和DA6及其溴化产物无疑通过单晶X射线衍射进行了表征。随后用双(9-甲基-9H-咔唑-3-基)胺(BMCA)电子给体进行胺化反应,得到了具有有益性质的D-π-D型半导体BA7-BMCA和DA6-BMCA,可作为钙钛矿太阳能电池的空穴传输材料。与基于BA7-BMCA器件的19.4%的最高功率转换效率(PCE)相比,DA6-BMCA对应器件的PCE更高,为20.2%,这可能归因于其具有扩展π共轭体系的S形双螺旋烯状连接体。