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- Title
Preparation, Characterization, Redox, and Photoinduced Electron-Transfer Properties of the NIR-Absorbing N-Ferrocenyl-2-pyridone BODIPYs.
- Authors
Zatsikha, Yuriy V.; Didukh, Natalia O.; Blesener, Tanner; Kayser, Mathew P.; Kovtun, Yuriy P.; Blank, David A.; Nemykin, Victor N.
- 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.
- Subjects
FERROCENE derivatives; PYRIDONE derivatives; OXIDATION-reduction reaction; PHOTOINDUCED electron transfer; DIPYRRINS; NEAR infrared spectroscopy; DENSITY functional theory; RING formation (Chemistry)
- Publication
European Journal of Inorganic Chemistry, 2017, Vol 2017, Issue 2, p318
- ISSN
1434-1948
- Publication type
Article
- DOI
10.1002/ejic.201600855