Pyrene-fused Dibenzoazatetracenes: Synthesis, Crystal Structures, Photophysical Properties and their Morphologies

Wang, Qingsong; Gao, Wei; Chen, Yan; Wang, Xiaohui; Zeng, Jin; Liu, Yiwei; Ran, Huijuan; Hu, Zhen; Bai, Jie; Feng, Xing; Redshaw, Carl; Chen, Qing; Hu, Jian Yong

Abstract

Molecular packing and microstructure can play a crucial role in the photophysical and electronic properties of organic semiconductor materials. This article presents six pyrene-fused dibenzoazatetracenes 3 and the relationship between their molecular structures and the emission, and as well as the morphology has been investigated. All of the compounds display an aggregation-caused emission quenching effect due to the extended π-conjugation associated with the close π-π stacking in their crystal structures. In terms of fluorescence, the compounds emitted sky-blue emission with a maximum peak (λmaxem) in the range 469–474 nm with a quantum yield (Φf) of 0.37–0.50 in solution. In the solid state, the emission maximum red-shifts to ∼528 nm and possesses a relatively low quantum yield (Φf) of 0.37–0.50 in solution. In the solid state, the emission maximum red‐shifts to ∼528 nm and possesses a relatively low quantum yield ( < 0.16). In addition, the electronic effects of the terminal group shows only a limited effect on the emission behavior. On the other hand, tert‐butyl groups have been introduced at the pyrene core, and contribute to enhance the solubility of the compound, and also improve the quality of the morphology.

Citation

Wang, Q., Gao, W., Chen, Y., Wang, X., Zeng, J., Liu, Y., Ran, H., Hu, Z., Bai, J., Feng, X., Redshaw, C., Chen, Q., & Hu, J. Y. (2021). Pyrene-fused Dibenzoazatetracenes: Synthesis, Crystal Structures, Photophysical Properties and their Morphologies. Asian journal of organic chemistry an ACES journal, 10(1), 233-240. https://doi.org/10.1002/ajoc.202000616

• Journal Article Type: Article
• Acceptance Date: Dec 2, 2020
• Online Publication Date: Dec 2, 2020
• Publication Date: 2021-01
• Deposit Date: Feb 10, 2021
• Publicly Available Date: Dec 3, 2021
• Journal: Asian Journal of Organic Chemistry
• Print ISSN: 2193-5807
• Publisher: Wiley-VCH Verlag
• Peer Reviewed: Peer Reviewed
• Volume: 10
• Issue: 1
• Pages: 233-240
• DOI: https://doi.org/10.1002/ajoc.202000616
• Keywords: Pyrene; Crystal structure; Structure-properties; Morphologies; Organic electronic
• Public URL: https://hull-repository.worktribe.com/output/3681857
• Publisher URL: https://onlinelibrary.wiley.com/doi/10.1002/ajoc.202000616