Unravelling the Superiority of Nonbenzenoid Acepleiadylene as a Building Block for Organic Semiconducting Materials

• Published in: Angewandte Chemie Vol. 135; no. 36
• Main Authors: Fu, Lin, Liu, Pengcai, Xue, Rui, Tang, Xiao‐Yu, Cao, Jiawen, Yao, Ze‐Fan, Liu, Yuchao, Yan, Shouke, Wang, Xiao‐Ye
• Format: Journal Article
• Language: English
• Published: Weinheim Wiley Subscription Services, Inc 04.09.2023
• Subjects: Acepleiadylene; Aggregation; Aromatic compounds; Chemistry; Dipoles; Donor-Acceptor Systems; Isomers; Nonbenzenoid Arenes; Optoelectronics; Pyrene; Semiconductors
• ISSN: 0044-8249; 1521-3757
• DOI: 10.1002/ange.202306509

Acepleiadylene (APD), a nonbenzenoid isomer of pyrene, exhibits a unique charge‐separated character with a large molecular dipole and a small optical gap. However, APD has never been explored in optoelectronic materials to take advantage of these appealing properties. Here, we employ APD as a building block in organic semiconducting materials for the first time, and unravel the superiority of nonbenzenoid APD in electronic applications. We have synthesized an APD derivative (APD‐IID) with APD as the terminal donor moieties and isoindigo (IID) as the acceptor core. Theoretical and experimental investigations reveal that APD‐IID has an obvious charge‐separated structure and enhanced intermolecular interactions as compared with its pyrene‐based isomers. As a result, APD‐IID displays significantly higher hole mobilities than those of the pyrene‐based counterparts. These results imply the advantages of employing APD in semiconducting materials and great potential of nonbenzenoid polycyclic arenes for optoelectronic applications. Nonbenzenoid acepleiadylene (APD) has been explored as a new building block to construct organic electronic material (APD‐IID), which exhibits higher hole mobility than its pyrene‐based isomers because of the stronger intermolecular interaction induced by the unique charge‐separated character. These results demonstrate the superiority of nonbenzenoid arenes in the future development of organic semiconducting materials.