Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 87, Issue 19, Pages 12741-12748Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.2c01303
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Funding
- National Natural Science Foundation of China [21975054]
- Natural Science Foundation of Guangdong Province of China [2019A1515010925]
- Guangdong Provincial Key Laboratory of Information Photonics Technology [2020B121201011]
- One Hundred Talents Program of the Guangdong University of Technology (GDUT) [1108-220413205]
- Open Fund of Guangdong Provincial Key Laboratory of Luminescence from Molecular Aggregates, Guangzhou, China [2019B030301003]
- Science and Technology Planning Project of Hunan Province [2018TP1017]
- University of Hull
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This study presents an efficient one-pot synthesis method for novel pyreno[2,1-b]furan molecules and demonstrates their intense green emission in solution and large red shift emission in the solid state due to strong ir-ir stacking. Furthermore, these compounds display novel two-photon absorption properties, with the TPA cross-section value increased by regulating the substituents' electronic effects. This research not only offers a facile strategy for constructing new luminescence materials with two-photon absorption properties but also provides a new chemical intermediate that opens up a new pathway to advanced materials.
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.
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