Diazulenorubicene as a Non‐benzenoid Isomer of peri‐Tetracene with Two Sets of 5/7/5 Membered Rings Showing Good Semiconducting Properties

Author:

Qin Liyuan12,Huang Yan‐Ying12,Wu Botao3,Pan Jinliang3,Yang Junfang2,Zhang Jing1,Han Guangchao1,Yang Suyu1,Chen Liangliang1,Yin Zheng12,Shu Yilin12,Jiang Lang1,Yi Yuanping1,Peng Qian2,Zhou Xiong3,Li Cheng1,Zhang Guanxin1,Zhang Xi‐Sha124,Wu Kai3,Zhang Deqing12ORCID

Affiliation:

1. Beijing National Laboratory for Molecular Sciences CAS Key Laboratory of Organic Solids CAS Center of Excellence in Molecular Science Institute of Chemistry Chinese Academy of Sciences 100190 Beijing China

2. School of Chemical Sciences University of Chinese Academy of Sciences 100049 Beijing China

3. College of Chemistry and Molecular Engineering Peking University 100871 Beijing China

4. State Key Laboratory of Applied Organic Chemistry Lanzhou University 730000 Lanzhou China

Abstract

AbstractNon‐benzenoid polycyclic aromatic hydrocarbons (PAHs) have received a lot of attention because of their unique optical, electronic, and magnetic properties, but their synthesis remains challenging. Herein, we report a non‐benzenoid isomer of peri‐tetracene, diazulenorubicene (DAR), with two sets of 5/7/5 membered rings synthesized by a (3+2) annulation reaction. Compared with the precursor containing only 5/7 membered rings, the newly formed five membered rings switch the aromaticity of the original heptagon/pentagon from antiaromatic/aromatic to non‐aromatic/antiaromatic respectively, modify the intermolecular packing modes, and lower the LUMO levels. Notably, compound 2 b (DAR‐TMS) shows p‐type semiconducting properties with a hole mobility up to 1.27 cm2 V−1 s−1. Moreover, further extension to larger non‐benzenoid PAHs with 19 rings was achieved through on‐surface chemistry from the DAR derivative with one alkynyl group.

Funder

National Natural Science Foundation of China

CAS-Croucher Funding Scheme for Joint Laboratories

Youth Innovation Promotion Association of the Chinese Academy of Sciences

Chinese Academy of Sciences

Publisher

Wiley

Subject

General Medicine

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