Premium
Synthesis, Structure and Conformation of Terphenylene‐Derived Oxacalixaromatics
Author(s) -
Hu WenJing,
Zhao XiaoLi,
Ma MingLiang,
Guo Fang,
Mi XianQiang,
Jiang Biao,
Wen Ke
Publication year - 2012
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.201101599
Subject(s) - chemistry , pyrazine , molecule , terphenyl , benzene , stereochemistry , crystal structure , solid state , diol , crystallography , organic chemistry
Oxacalix[4]aromatics comprised of terphenylene units have been synthesized by cyclooligomerization of 5′‐ tert ‐butyl‐1,1′:3′,1″‐terphenyl‐4,4″‐diol ( 1 ) and electron‐deficient meta ‐dihalogenated benzene and heterocycles. Single‐crystal X‐ray analysis revealed that oxacalix[2]terphenylene[2]pyrazine 13 adopts a chair conformation, forming a molecular cavity to trap an ethyl acetate guest molecule in the solid state. 1,3‐Alternate conformations are adopted by other oxacalix[2]terphenylene[2]aromatics ( 11 , 12 and 15 ), which form a narrow tweezer‐like molecular cavity that is incapable of encapsulating any guest molecules.