Near-Infrared Aza-BODIPY Dyes

  • ChemPubSoc Europe Logo
  • Author: Andrei Dragan
  • Published Date: 10 September 2017
  • Source / Publisher: Chemistry – An Asian Journal/Wiley-VCH
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA
thumbnail image: Near-Infrared Aza-BODIPY Dyes

Near-infrared (NIR) dyes have broad applications in both materials and biological science. Aza-BODIPYs (BF2-complexed aza-dipyrrins) generally exhibit a strong absorption around 650 nm and have been extensively studied.


Changjiang Yu, Lijuan Jiao, Anhui Normal University, China, Petia Bobadova-Parvanova, Rockhurst University, Kansas City, MO, USA, and colleagues have efficiently fused phenanthrene to an aza-dipyrrin core through a tandem Suzuki reaction/intramolecular oxidative ring-fusion reaction or a palladium-catalyzed intramolecular C–H activation reaction.

The resulting [b]-phenanthrene-fused aza-BODIPY dyes have a strong NIR absorption centered at 771 nm, and emission bands at around 800 nm. Importantly, these dyes exhibit high photostability due to the pronounced stabilization of the LUMO (lowest unoccupied molecular orbital) upon annulations. The dyes have potential as organic photovoltaic materials and are an addition to the pool of NIR dyes.


 

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