Visible-Light-Induced Direct Photoamination of BODIPY Dyes with Aqueous Ammonia
Dandan Wang, Long Wang, Xing Guo, Xiankang Zhang, Juan Ma, Zhengxin Kang, Zhongyuan Li, Lijuan Jiao, Erhong Hao
Abstract
By taking advantage of their strong absorption ability, visible-light-induced direct photoamination of BODIPY dyes with aqueous ammonia was developed to give structurally diverse α-amino BODIPYs. The excited state of BODIPYs possessed higher electron affinity than the ground state and thus showed largely enhanced reactivity toward weak nucleophile of ammonia. Those α-amino BODIPYs are valuable synthetic intermediates and have been successfully demonstrated in several post-transformation reactions. The work indicates that photoreaction is an excellent alternative to conventional functionalization of this popular fluorophore.
Topics & Concepts
ChemistryBODIPYFluorophorePhotochemistryNucleophileAqueous solutionAmmoniaReactivity (psychology)Excited stateFluorescenceAbsorption (acoustics)Visible spectrumCombinatorial chemistryOrganic chemistryCatalysisMedicinePhysicsAlternative medicinePathologyNuclear physicsQuantum mechanicsOptoelectronicsAcousticsLuminescence and Fluorescent MaterialsPorphyrin and Phthalocyanine ChemistryNanoplatforms for cancer theranostics