Fluorinated azobenzenes with highly strained geometries for halogen bond-driven self-assembly in the solid state

被引:28
作者
Bushuyev, Oleksandr S. [1 ]
Tan, Davin
Barrett, Christopher J.
Friscic, Tomislav
机构
[1] McGill Univ, Dept Chem, Montreal, PQ H3A 0B8, Canada
基金
加拿大自然科学与工程研究理事会; 加拿大创新基金会;
关键词
ISOSTRUCTURAL MATERIALS; MOLECULAR-STRUCTURE; TRANS-AZOBENZENE; SINGLE-CRYSTALS; HYDROGEN-BOND; ISOMERIZATION; REACTIVITY; MOTION; PHOTOISOMERIZATION; DIRECTIONALITY;
D O I
10.1039/c4ce01216j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Attempted cocrystallisation of brominated and iodinated octafluoroazobenzene derivatives with morpholine led to the exhaustive replacement of fluorine substituents that are in ortho-positions to the azobenzene with sterically demanding morpholine groups. The resulting molecules exhibit a highly unusual strained conformation of the azobenzene unit, in which the terminal phenyl rings adopt a mutually nearly completely orthogonal orientation. Substitution of ortho-fluorine groups with N-morpholine fragments provides molecules with active halogen bond donor and acceptor sites that guide the molecular selfassembly in the solid state towards the formation of polymeric halogen-bonded chains.
引用
收藏
页码:73 / 80
页数:8
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