Preparation, Characterization, Redox, and Photoinduced Electron-Transfer Properties of the NIR-Absorbing N-Ferrocenyl-2-pyridone BODIPYs

Yuriy V. Zatsikha, Natalia O. Didukh, Tanner Blesener, Mathew P. Kayser, Yuriy P. Kovtun, David A. Blank, Victor N. Nemykin

Research output: Contribution to journalArticlepeer-review

22 Scopus citations

Abstract

Mono- and di-(N-ferrocenyl-2-pyridone)-containing BODIPYs were prepared using a set of ferrocene-enamine cyclization reactions. The target compounds were characterized by UV-Vis, NMR, and mass spectrometry, while their redox properties were probed by the electrochemical, spectroelectrochemical, and chemical oxidation methods. Redox properties of the di-(ferrocenyl)-containing BODIPY are suggestive of a lack of electronic coupling between the two ferrocene groups. Oxidation of the ferrocene(s) in the target BODIPYs results in their observable fluorescence, while transient absorption spectroscopy data indicate fast electron-transfer from ferrocene donor to the photoexcited BODIPY acceptor. Density functional theory (DFT) and time-dependent DFT (TDDFT) methods were used to elucidate electronic structures of the organometallic BODIPYs and confirm the presence of the low-energy metal-to-ligand charge-transfer states in the NIR region.

Original languageEnglish (US)
Pages (from-to)318-324
Number of pages7
JournalEuropean Journal of Inorganic Chemistry
Volume2017
Issue number2
DOIs
StatePublished - Jan 10 2017

Bibliographical note

Publisher Copyright:
© 2017 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

Keywords

  • Density functional calculations
  • Donor–acceptor systems
  • Electron transfer
  • Photophysics
  • UV/Vis spectroscopy

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