Chrysene‐Based Azahelicene π‐Linker of D‐π‐D‐Type Hole‐Transporting Materials for Perovskite Solar Cells

• Published in: ChemSusChem 2021-11, Vol.14 (22), p.4923-4928
• Main Authors: Tang, Zefeng, Li, Tianyu, Cao, Yucai, Zhang, Yuyan, He, Lifei, Zheng, Aibin, Lei, Ming
• Format: Article
• Language: English
• Subjects: Bromination; Chemical reactions; conjugation; Diamines; Energy conversion efficiency; hole-transporting materials; Organic chemistry; Perovskites; Photovoltaic cells; Polycyclic aromatic hydrocarbons; Single crystals; Solar cells
• ISSN: 1864-5631; 1864-564X
• DOI: 10.1002/cssc.202101551

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 N6,N12‐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. Advanced D‐π‐D: Two chrysene‐based azahelicenes‐BA7 and DA6‐were constructed and linked with the electron donor bis(9‐methyl‐9H‐carbazol‐3‐yl)amine (BMCA) to afford D‐π‐D‐type hole‐transporting materials for perovskite solar cells. The higher efficiency of the DA6‐BMCA‐based device may be attributed to its extended S‐shaped double helical π‐conjugated system.