1. Preparation and reactions of 4,4-dilithiodithienogermole
- Author
-
Yousuke Ooyama, Joji Ohshita, Yohei Adachi, Taishi Nabeya, and Jun Hyun Song
- Subjects
Steric effects ,Trimethylsilyl chloride ,Absorption spectroscopy ,Trimethylsilyl ,010405 organic chemistry ,Organic Chemistry ,chemistry.chemical_element ,010402 general chemistry ,01 natural sciences ,Biochemistry ,Medicinal chemistry ,0104 chemical sciences ,Inorganic Chemistry ,chemistry.chemical_compound ,chemistry ,Yield (chemistry) ,Materials Chemistry ,Lithium ,Physical and Theoretical Chemistry ,Fluoride ,Methyl iodide - Abstract
The reaction of 4,4-dichloro-2,6-di(n-butyl)dithienogermole (DTGCl) with lithium naphthalenide yielded a dark blue solution, which was treated with methyl iodide to provide a 4,4-dimethylated product in 67% isolated yield, indicating the formation of 4,4-dilithio-2,6-di(n-butyl)dithienogermole (DTGLi). Similar treatment of the dark blue solution containing DTGLi with trimethylsilyl fluoride and water gave the corresponding 4,4-disubstituted products. When trimethylsilyl chloride was used, however, no silylated products were obtained, likely due to steric hindrance. The reaction of DTGLi with DTGCl gave poly[2,6-di(n-butyl)dithienogermole-4,4-diyl], whose UV–vis absorption spectra revealed a more extended conjugation than that of a previously prepared product from the Wurtz-type coupling of DTGCl with sodium. Reinvestigation of the electronic states of poly(dithienogermole-4,4-diyl) derivatives on the basis of crystal orbital calculations was also accomplished.
- Published
- 2019