Premium
Optically Active 2,7,10,15‐Tetrahydroxytetraphenylene: Clathrates with Both Enantiomers of 1‐Phenylethylamine and Their Stability
Author(s) -
Kaku Hiroto,
Mitarai Akinobu,
Okamoto Natsuko,
Tanaka Kenta,
Ichikawa Sayaka,
Yamamoto Takahiro,
Inai Makoto,
Nishii Takeshi,
Horikawa Mitsuyo,
Tsunoda Tetsuto
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201801422
Subject(s) - chemistry , enantiomer , thermal stability , enantiomeric excess , yield (engineering) , toluene , stereochemistry , medicinal chemistry , enantioselective synthesis , organic chemistry , catalysis , materials science , metallurgy
2,7,10,15‐Tetrahydroxytetraphenylene (THTP) was synthesized in two steps by the homo‐coupling reaction of 2,2′‐dibromo‐5,5′‐dimethoxybiphenyl. Optical resolution of racemic THTP was achieved by complexation with ( S )‐1‐phenylethylamine in toluene to afford ( S , S )‐THTP in good yield. ( R , R )‐THTP was also obtained using ( R )‐1‐phenylethylamine. In the course of these studies, ( S , S )‐THTP constituted an inclusion compound even with ( R )‐1‐phenylethylamine. Both complexes were characterized by X‐ray structural analyses and the thermal analyses (DSC and TGA). The hydrogen bonding networks of the complex with ( R )‐1‐phenylethylamine are more complicated than those of the complex with ( S )‐1‐phenylethylamine. The thermal analysis suggests that the complex with ( S )‐1‐phenylethylamine is a less stable clathrate than the complex with ( R )‐1‐phenylethylamine.