One-Pot Synthesis of Pyreno[2,1-b]furan Molecules with Two-Photon Absorption Properties

Wang, Xiaohui; Zhang, Chengjing; Zeng, Jin; Mao, Xiaoyu; Redshaw, Carl; Niu, Guangle; Yu, Xiaoqiang; Feng, Xing

Abstract

The development of large π-conjugated polycyclic heteroaromatic materials is of immense interest, both in the academic as well as the industrial community. Herein, we present the efficient one-pot synthesis of novel pyreno[2,1-b]furan molecules from a newly designed intermediate, which display intense green emission (505-516 nm) in solution and a large red shift emission (625-640 nm) in the solid state, because of strong π-πstacking. More interestingly, the compounds exhibit novel two-photon absorption (TPA) properties, and the TPA cross-section (η´) value was increased to 533 GM by regulating the electronic effects of the substituents of the pyreno[2,1-b]furan molecules. This study not only offers a facile strategy for constructing new pyrene-fused luminescence materials with two-photon absorption properties but also provides a new chemical intermediate that opens up a new pathway to advanced materials.

Citation

Wang, X., Zhang, C., Zeng, J., Mao, X., Redshaw, C., Niu, G., Yu, X., & Feng, X. (2022). One-Pot Synthesis of Pyreno[2,1-b]furan Molecules with Two-Photon Absorption Properties. Journal of Organic Chemistry, https://doi.org/10.1021/acs.joc.2c01303

• Journal Article Type: Article
• Acceptance Date: Aug 16, 2022
• Online Publication Date: Sep 8, 2022
• Publication Date: 2022
• Deposit Date: Sep 8, 2022
• Publicly Available Date: Sep 9, 2023
• Journal: The Journal of Organic Chemistry
• Print ISSN: 0022-3263
• Electronic ISSN: 1520-6904
• Publisher: American Chemical Society
• Peer Reviewed: Peer Reviewed
• DOI: https://doi.org/10.1021/acs.joc.2c01303
• Keywords: Absorption; Fluorescence; Mixtures; Molecules; Quantum mechanics
• Public URL: https://hull-repository.worktribe.com/output/4068777