Journal
RSC ADVANCES
Volume 5, Issue 58, Pages 46534-46539Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c5ra05920h
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Funding
- American Chemical Society Petroleum Research Fund [SPN00045]
- National Science Foundation [MRI-0821515]
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Selective sulfur substitution of the distal carbonyls of a core-substituted naphthalene diimide was obtained when a combination of core and imide substituents were used. The substituents appear to inhibit thionation of the proximal carbonyl by steric hindrance. Each thionation caused a 50 nm bathochromic shift of the visible absorption band and an anodic shift of the reduction potentials. The dithionated compound has a lambda(max) in the near-IR at 733 nm and an optical gap of 1.59 eV, which is unusually low for this type of molecule. Thionation of carbonyls offers a useful avenue for tuning optoelectronic properties of NDI-based materials.
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