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

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

2022The Journal of Organic Chemistry19 citationsDOIOpen Access PDF

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-π stacking. More interestingly, the compounds exhibit novel two-photon absorption (TPA) properties, and the TPA cross-section (δ) 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.

Topics & Concepts

FuranPyreneAbsorption (acoustics)StackingMoleculeConjugated systemTwo-photon absorptionPhotochemistryLuminescenceMaterials scienceChemistryOrganic chemistryOptoelectronicsPolymerPhysicsOpticsLaserComposite materialLuminescence and Fluorescent MaterialsPorphyrin and Phthalocyanine ChemistryOrganic Light-Emitting Diodes Research