Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 80, Issue 21, Pages 10742-10756Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.5b01963
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Funding
- MEXT
- Japan Society for the Promotion of Science (JSPS) [25410091]
- [2408]
- [15H00933]
- [24109013]
- Grants-in-Aid for Scientific Research [25410091, 24109013, 26620028, 25288021] Funding Source: KAKEN
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A series of 5-N-arylaminothiazoles was prepared by reacting thioamide dianions derived from secondary thioamides with thioformamides, followed by sequential oxidation with iodine. X-ray analyses demonstrated that they adopt structures that are highly twisted from planar conformations. Their orientations were tuned by the steric and/or electronic interactions of the substituents at their 2-, 4-, and 5-positions. The 5-aminothiazoles exhibited a range of fluorescent emissions, from blue to orange. Although the absorption spectra were independent of the polarity of the solvent, fluorescent emissions were influenced by the polarity of the solvent: in more polar solvents, the emissions were red-shifted. These phenomena were examined in terms of Lippert-Mataga plots and the change in the dipole moment between the ground and excited states. They also exhibited emissions in the solid state, again from blue to orange. Cyclic voltammetry of the 5-aminothiazoles showed reversible waves of one-electron oxidation. The half-potential of the oxidation was reduced by the introduction of electron-donating groups to the phenyl groups on the nitrogen atom at the 5-position. DFT calculations were carried out to determine the energy levels of the HOMO and LUMO. Finally, the results of TG-DTA showed that they are thermally stable.
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