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

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

来源：Journal of Organic Chemistry, 2022, 87(19): 12741-12748.

DOI：10.1021/acs.joc.2c01303

• ELECTROGENERATED CHEMILUMINESCENCE
• CYCLIZATION REACTION
• PYRENE
• SUBSTITUTION
• DERIVATIVES

The development of large ir-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 ir-ir stacking. More interestingly, the compounds exhibit novel two-photon absorption (TPA) properties, and the TPA cross-section (6) 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.

• 单位
  山东大学; 6; 广东工业大学