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Post-Modification of Pyrrolopyrrole Aza-BODIPY toward High Near-Infrared Fluorescence Brightness

Yitong Wang, Shigeki Mori, Hajime Nakanotani, Chihaya Adachi, Soji Shimizu

2023Organic Letters16 citationsDOIOpen Access PDF

Abstract

Pyrrolopyrrole aza-BODIPYs (PPABs), dimeric aza-BODIPY analogues, exhibit intense absorption and fluorescence in the visible and near-infrared (NIR) regions. Here, we developed a facile postmodification by palladium-catalyzed coupling reactions to synthesize a series of donor-acceptor-donor (D-A-D) PPABs. Despite the possible fluorescence quenching dictated by the energy-gap low, D-A-D PPABs exhibit high-fluorescence brightness in the NIR region, implying their potential use as a bright NIR emitter.

Topics & Concepts

BODIPYChemistryFluorescencePhotochemistryQuenching (fluorescence)Absorption (acoustics)Near-infrared spectroscopyInfraredAcceptorBrightnessPalladiumCatalysisOrganic chemistryMaterials scienceOpticsComposite materialCondensed matter physicsPhysicsLuminescence and Fluorescent MaterialsNanoplatforms for cancer theranosticsPorphyrin and Phthalocyanine Chemistry
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