The Impact of C2 Insertion into a Carbazole Donor on the Physicochemical Properties of Dibenzo[a,j]phenazine-Cored Donor–Acceptor–Donor Triads

Zimmermann Crocomo, Paola; Kaihara, Takahito; Kawaguchi, Soki; Stachelek, Patrycja; Minakata, Satoshi; Silva, Piotr; Data, Przemyslaw; Takeda, Youhei

Abstract

Novel electron donor–acceptor–donor (D-A-D) compounds comprising dibenzo[a,j]phenazine as the central acceptor core and two 7-membered diarylamines (iminodibenzyl and iminostilbene) as the donors have been designed and synthesized. Investigation of their physicochemical properties revealed the impact of C2 insertion into well-known carbazole electron donors on the properties of previously reported twisted dibenzo[a,j]phenazine-core D-A-D triads. Slight structural modification caused a drastic change in conformational preference, allowing unique photophysical behavior of dual emission derived from room-temperature phosphorescence and triplet–triplet annihilation. Furthermore, electrochemical analysis suggested sigma-dimer formation and electrochemical polymerization on the electrode. Quantum chemical calculations also rationalized the experimental results.

Citation

Zimmermann Crocomo, P., Kaihara, T., Kawaguchi, S., Stachelek, P., Minakata, S., Silva, P., Data, P., & Takeda, Y. (2021). The Impact of C2 Insertion into a Carbazole Donor on the Physicochemical Properties of Dibenzo[a,j]phenazine-Cored Donor–Acceptor–Donor Triads. Chemistry - A European Journal, 27(53), 13390-13398. https://doi.org/10.1002/chem.202101654

• Journal Article Type: Article
• Acceptance Date: Jun 10, 2021
• Online Publication Date: Jul 27, 2021
• Publication Date: Sep 20, 2021
• Deposit Date: May 10, 2023
• Publicly Available Date: Aug 4, 2023
• Journal: Chemistry – A European Journal
• Print ISSN: 0947-6539
• Electronic ISSN: 1521-3765
• Publisher: Wiley
• Volume: 27
• Issue: 53
• Pages: 13390-13398
• DOI: https://doi.org/10.1002/chem.202101654
• Public URL: https://durham-repository.worktribe.com/output/1174830