Aryl-Boron-Substituted BODIPYs: Direct Access via Aluminum-Chloride-Mediated Arylation from Arylstannanes and Tuning the Optoelectronic Properties
Zhaoyun Wang, Xing Guo, Zhengxin Kang, Qinghua Wu, Heng Li, Cheng Cheng, Changjiang Yu, Lijuan Jiao, Erhong Hao
Abstract
An efficient procedure is presented for functionalization of BODIPYs at boron with arylstannanes as weak nucleophiles in the presence of aluminum chloride, providing new aryl-boron-substituted BODIPY and aza-BODIPY derivatives of singular importance. Most of these aryl-boron-substituted BODIPYs showed bright emission in the aqueous solution with significant aggregation-induced emission enhancement and high solid-state emission as a result of the restricted rotation of the meso -phenyl group and boron-substituted aryl groups as well as the formation of J -type aggregates.
Topics & Concepts
ChemistryBoronBODIPYArylNucleophileAluminiumChloridePhotochemistryAqueous solutionCombinatorial chemistryOrganic chemistryCatalysisFluorescenceAlkylQuantum mechanicsPhysicsLuminescence and Fluorescent MaterialsOrganic Light-Emitting Diodes ResearchMolecular Sensors and Ion Detection