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

Qinqin Shi; Xiaosong Shi; Changfu Feng; Yishi Wu; Nan Zheng; Jie Liu; Xiaoxi Wu; Hao Chen; Aidong Peng; Jianfeng Li; Lang Jiang; Hongbing Fu; Zengqi Xie; Seth R Marder; Simon B Blakey; Hui Huang

doi:10.1002/anie.202014108

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

Angew Chem Int Ed Engl. 2021 Feb 8;60(6):2924-2928. doi: 10.1002/anie.202014108. Epub 2020 Dec 10.

Authors

Qinqin Shi¹, Xiaosong Shi², Changfu Feng³, Yishi Wu³, Nan Zheng⁴, Jie Liu², Xiaoxi Wu¹, Hao Chen¹, Aidong Peng¹, Jianfeng Li¹, Lang Jiang², Hongbing Fu³, Zengqi Xie⁴, Seth R Marder⁵, Simon B Blakey⁶, Hui Huang¹

Affiliations

¹ Center of Materials Science and Optoelectronics Engineering, College of Materials Science and Opto-Electronic Technology & CAS Center for Excellence in Topological Quantum Computation & CAS Key Laboratory of Vacuum Physic, University of Chinese Academy of Sciences, Beijing, 100049, P. R. China.
² Key Laboratory of Organic Solids, Beijing National Laboratory for Molecular Science, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190, P. R. China.
³ Beijing Key Laboratory for Optical Materials and Photonic Devices, Department of Chemistry, Capital Normal University, Beijing, 100048, P. R. China.
⁴ State Key Laboratory of Luminescent Materials and Devices, School of Materials Science and Engineering, South China University of Technology, Guangzhou, 510640, P. R. China.
⁵ School of Chemistry and Biochemistry and Center for Organic Photonics and Electronics, Georgia Institute of Technology, Atlanta, GA, 30332, USA.
⁶ Department of Chemistry, Emory University, Atlanta, GA, 30322, USA.

PMID: 33107179
DOI: 10.1002/anie.202014108

Abstract

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.

Keywords: cross-coupling; cyclization; polycyclic aromatic hydrocarbons; structure elucidation; synthetic methods.

Abstract

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