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Palladium(II)-Catalyzed Dehydrogenative Strategy for Direct and Regioselective Oligomerization of BODIPY Dyes

Zhengxin Kang, Fan Lv, Qinghua Wu, Heng Li, Zhongxin Li, Feng-xi Wu, Zhaoyun Wang, Lijuan Jiao, Erhong Hao

2021Organic Letters22 citationsDOI

Abstract

A family of directly β,γ-linked BODIPY oligomers up to pentamers were regioselectively prepared via Pd(II)-catalyzed oxidative C–H cross-coupling. The structural integrity of β,γ-linked dimers was unambiguously confirmed by X-ray crystallography. These structurally unprecedented oligomers showed red-shifted absorptions and near-infrared emissions along with efficient intersystem crossing, giving ΦΔ in the range of 12–43%, for potential use as heavy-atom-free photosensitizers.

Topics & Concepts

ChemistryBODIPYRegioselectivityPalladiumCatalysisIntersystem crossingPhotochemistryOxidative phosphorylationCombinatorial chemistryFluorescenceOrganic chemistryExcited stateSinglet statePhysicsQuantum mechanicsNuclear physicsBiochemistryLuminescence and Fluorescent MaterialsNanoplatforms for cancer theranosticsPorphyrin and Phthalocyanine Chemistry
Palladium(II)-Catalyzed Dehydrogenative Strategy for Direct and Regioselective Oligomerization of BODIPY Dyes | Litcius