Forrest Etheridge | Case Western Reserve University (original) (raw)
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Selective sulfur substitution of the distal carbonyls of a core-substituted naphthalene diimide w... more 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
lmax 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 NDIbased
materials.
New J. Chem., 2015
The effect of styryl imide substitution on optical and electrochemical properties of core-substit... more The effect of styryl imide substitution on optical and electrochemical properties of core-substituted naphthalenediimides was examined by synthesizing a series of naphthalenediimide molecules. 2-Ethylhexylamino and 5-(2-ethylhexyl)thiophene groups were used as core substituents. The optical and electrochemical properties of styryl imide substituted compounds were compared with other imide substitutions including hydrogen, 2-ethylhexyl, and 4-thienylphenyl. Generally, the imide substituents had little effect on the optical properties, except when the combination of alkylamino core and styryl imide substituents was used. In this latter case, we observed a 104 nm red-shift of the absorption onset upon film formation, resulting in an unusually broad visible absorption (500-800 nm) for these types of molecules. This is explained by the planarity of the molecule and the formation of intermolecular aromatic donor-acceptor type interactions. These results show that imide substituents play a role in tuning opto-electronic properties of NDI molecules, and that NDI molecules with styryl imide substituents merit further evaluation for opto-electronic applications. † Electronic supplementary information (ESI) available: Reaction conditions tested for Chan-Lam coupling reaction of RF8H, 1 H NMR spectra, MALDI-TOF mass spectra, emission spectra, and computational data (FMOs of all molecules, and cartesian coordinates, frequencies and energies of the optimized geometries). See
Selective sulfur substitution of the distal carbonyls of a core-substituted naphthalene diimide w... more 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
lmax 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 NDIbased
materials.
New J. Chem., 2015
The effect of styryl imide substitution on optical and electrochemical properties of core-substit... more The effect of styryl imide substitution on optical and electrochemical properties of core-substituted naphthalenediimides was examined by synthesizing a series of naphthalenediimide molecules. 2-Ethylhexylamino and 5-(2-ethylhexyl)thiophene groups were used as core substituents. The optical and electrochemical properties of styryl imide substituted compounds were compared with other imide substitutions including hydrogen, 2-ethylhexyl, and 4-thienylphenyl. Generally, the imide substituents had little effect on the optical properties, except when the combination of alkylamino core and styryl imide substituents was used. In this latter case, we observed a 104 nm red-shift of the absorption onset upon film formation, resulting in an unusually broad visible absorption (500-800 nm) for these types of molecules. This is explained by the planarity of the molecule and the formation of intermolecular aromatic donor-acceptor type interactions. These results show that imide substituents play a role in tuning opto-electronic properties of NDI molecules, and that NDI molecules with styryl imide substituents merit further evaluation for opto-electronic applications. † Electronic supplementary information (ESI) available: Reaction conditions tested for Chan-Lam coupling reaction of RF8H, 1 H NMR spectra, MALDI-TOF mass spectra, emission spectra, and computational data (FMOs of all molecules, and cartesian coordinates, frequencies and energies of the optimized geometries). See