Near-Infrared Twisted Polycyclic Arene-Fused BisBODIPYs through a Tandem Inter- and Intramolecular Scholl Reaction
Huiquan Zuo, Qinghua Wu, Long Wang, Zhengxin Kang, Heng Li, Hua Wang, Xing Guo, Jiangang Gao, Erhong Hao, Lijuan Jiao
Abstract
Five novel polyaromatic-ring-fused bisBODIPYs have been synthesized from corresponding readily available α-arylBODIPYs through a FeCl 3 -mediated tandem inter- and intramolecular oxidative aromatic coupling reaction. These resultant bisBODIPYs show twisted planar conformations, strong absorptions (ε up to 1.8 × 10 5 M –1 cm –1 ), and good fluorescence emissions in the near-infrared region (NIR, 660–734 nm) and good intersystem crossing efficiencies (Φ Δ = 18.9% for dimer 2d in toluene), demonstrating their promising potential applications as heavy-atom-free photosensitizers.
Topics & Concepts
ChemistryIntramolecular forceTandemInfraredPhotochemistryStereochemistryComputational chemistryMaterials sciencePhysicsComposite materialOpticsLuminescence and Fluorescent MaterialsOrganic Light-Emitting Diodes ResearchPorphyrin and Phthalocyanine Chemistry