Synthesis and electronics of donor-accepter linear arrays comprising anthracene bisimide with butadiynylene spacers

• Published in: Bulletin of the Chemical Society of Japan Vol. 97; no. 4
• Main Authors: Iwanaga, Tetsuo, Tanaka, Keisuke, Kawano, Kento
• Format: Journal Article
• Language: English
• Published: OXFORD Oxford Univ Press 01.04.2024
• Subjects: Chemistry; Chemistry, Multidisciplinary; Physical Sciences; Science & Technology; CORE; donor-accepter array; DIIMIDE; ABSORPTION; electronic property; anthracene bisimide
• ISSN: 0009-2673; 1348-0634
• DOI: 10.1093/bulcsj/uoae031

To further explore the pi-conjugated systems of anthracene bisimide (ABI) and investigate their electronic properties, we synthesized donor-accepter linear arrays. These arrays consist of an ABI unit as the accepter and a 9,10-anthrylene unit as the donor, linked by a butadiynylene spacer. We constructed these donor-accepter arrays through Hay coupling of the corresponding 9,10-diethynylABI derivative with a 9,10-diethynylanthracene derivative. Theoretical calculations and electronic spectra analysis were employed to compare the photophysical properties of these compounds with those of their acetylene analogs. Moreover, we evaluated the intramolecular electronic interactions between the ABI and anthrylene units, focusing on the effects of the butadiynylene spacer and array sequences. Graphical Abstract Donor-accepter linear arrays, comprising anthracene bisimide as the accepter and 9,10-anthrylene as the donor, connected by a butadiynylene spacer, were synthesized via Hay coupling. The electronic properties were examined through theoretical calculations and electronic spectra analysis, focusing on the effects of the spacer and array sequences.