Azuperylene: The Nonalternant Isomer of Perylene

S Shengpei Liu (Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, Sichuan University, 29 Wangjiang Road, Chengdu 610064, P. R. China) M Marcos Díaz‐Fernández (Department of Physical Chemistry University of Malaga Campus de Teatinos s/n Málaga 29071 Spain) M Menglin Zhang F Fei Huang Y Yong Chen Y Yudong Yang (Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, Sichuan University, 29 Wangjiang Road, Chengdu 610064, People’s Republic of China) J José Manuel Marín‐Beloqui (Department of Physical Chemistry University of Malaga Campus de Teatinos s/n Málaga 29071 Spain) J Jingbo Lan (Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry Sichuan University Chengdu People's Republic of China) J Jingsong You (Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry) J Juan Casado (Department of Physical Chemistry, University of Malaga, Campus de Teations s/n, Malaga 229071, Spain) C Cheng Zhang

Abstract

Abstract The isoelectronic isomer of perylene, hereafter called as azuperylene, has been prepared. Electronic structure analysis reveals that the new isomer can be described as a union of two antiparallel azulenes in which the azulene‐type aromatic character of the starting azulene is partially retained. Four 2,8‐dialkoxy (i.e., ethoxy, n ‐butoxy, n ‐hexyloxy, and n ‐octyloxy) functionalized derivatives of the new isomer core have been prepared. The solid‐state structures of the new compounds have been resolved showing exceptional herringbone π–π stacking ideal for charge transport. Organic field‐effect transistors on sublimated substrates display an excellent hole transport mobility up to 1.03 cm 2 V −1 s −1 that largely surpasses that of perylene and reveals the great potential for charge transport of this new class of nonbenzenoid compounds.

Article Details

Volume / Issue Vol. 64, Issue 29
Published July 14, 2025
ISSN 1433-7851
Publisher Wiley

Journal Info

Angewandte Chemie International Edition

Wiley

ISSN: 1433-7851 Physical Sciences

Authors (11)

S

Shengpei Liu

Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, Sichuan University, 29 Wangjiang Road, Chengdu 610064, P. R. China

M

Marcos Díaz‐Fernández

Department of Physical Chemistry University of Malaga Campus de Teatinos s/n Málaga 29071 Spain

M

Menglin Zhang

F

Fei Huang

Y

Yong Chen

Y

Yudong Yang

Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, Sichuan University, 29 Wangjiang Road, Chengdu 610064, People’s Republic of China

J

José Manuel Marín‐Beloqui

Department of Physical Chemistry University of Malaga Campus de Teatinos s/n Málaga 29071 Spain

J

Jingbo Lan

Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry Sichuan University Chengdu People's Republic of China

J

Jingsong You

Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry

J

Juan Casado

Department of Physical Chemistry, University of Malaga, Campus de Teations s/n, Malaga 229071, Spain

C

Cheng Zhang