Synthetic Routes for Heteroatom‐Containing Alkylated/Arylated Polycyclic Aromatic Hydrocarbons

• Published in: Angewandte Chemie International Edition Vol. 60; no. 6; pp. 2924 - 2928
• Main Authors: Shi, Qinqin, Shi, Xiaosong, Feng, Changfu, Wu, Yishi, Zheng, Nan, Liu, Jie, Wu, Xiaoxi, Chen, Hao, Peng, Aidong, Li, Jianfeng, Jiang, Lang, Fu, Hongbing, Xie, Zengqi, Marder, Seth R., Blakey, Simon B., Huang, Hui
• Format: Journal Article
• Language: English
• Published: Germany Wiley Subscription Services, Inc 08-02-2021
• Edition: International ed. in English
• Subjects: Absorption; Alkylation; Aromatic compounds; cross-coupling; cyclization; Magnetic resonance spectroscopy; NMR; NMR spectroscopy; Nuclear magnetic resonance; Polycyclic aromatic hydrocarbons; structure elucidation; synthetic methods; cross-coupling; structure elucidation; polycyclic aromatic hydrocarbons; cyclization; synthetic methods
• ISSN: 1433-7851; 1521-3773
• DOI: 10.1002/anie.202014108

Synthetic routes for heteroatom‐containing polycyclic aromatic hydrocarbons (H‐PAHs) with alkyl and aryl substitution are demonstrated. Three H‐PAHs, including heteroatom‐containing rubicenes (H‐rubicenes), angular‐benzothiophenes (ABTs), and indenothiophene (IDTs) were successfully synthesized by two key steps, including polysubstituted olefin formation and cyclization. Specifically, ABT and H‐rubicenes were comprehensively investigated by single‐crystal X‐ray diffraction, NMR spectroscopy, UV‐vis absorption, cyclic voltammetry, transient absorption, and single‐crystal OFET measurements.
Synthetic routes, including trisubstituted olefin formation and cyclization, were optimized for synthesizing three different heteroatom‐containing polycyclic aromatic hydrocarbons PAHs (H‐rubicenes, ABTs, and IDTs) in relatively high overall yields. Finally, crystal structures, optoelectronic, radiationless processes, and charge transport properties of chalcogen‐containing rubicenes were investigated to show their potential for organic semiconductors.