C3-Symmetrical Tribenzotriquinacene Derivatives: Optical Resolution through Cryptophane Synthesis and Supramolecular Self-Assembly into Nanotubes

被引：57
|
作者：
Wang, Tao [1 ,2 ]
Zhang, Yu-Fei [1 ,2 ]
Hou, Qm-Qing [1 ,2 ]
Xu, Wen-Rong [3 ,4 ]
Cao, Xiao-Ping [1 ,2 ]
Chow, Hak-Fun [3 ,4 ]
Kuck, Dietmar [5 ]
机构：
[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China
[2] Lanzhou Univ, Coll Chem & Chem Engn, Lanzhou 730000, Peoples R China
[3] Chinese Univ Hong Kong, Dept Chem, Hong Kong, Hong Kong, Peoples R China
[4] Chinese Univ Hong Kong, Inst Mol Funct Mat, UGC AoE Scheme, Hong Kong, Hong Kong, Peoples R China
[5] Univ Bielefeld, Dept Chem, D-33615 Bielefeld, Germany
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 78卷 / 03期
关键词：
CIRCULAR-DICHROISM; BUILDING-BLOCKS; HOSTS; COMPLEXES; CHEMISTRY; SYSTEMS; CAGES; C-60;
D O I：
10.1021/jo302470v
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Based on a regioselective tris-formylation of a tribenzotriquinacene (TBTQ) hydrocarbon, the racemic C-3-symmetrical TBTQ-trialdehyde and the corresponding TBTQ-trimethanol were synthesized along with their C-1-isomers. Conversion of the C-3-trialdehyde to three diastereomeric TBTQ-based cryptophanes occurring in high yield enabled the preparation of the optically pure C-3-symmetrical TBTQ-trialdehydes and the determination of their absolute configuration. The racemic C-3-symmetrical TBTQ-trimethanol was found to form several stable nanotubular aggregates in the solid state.
引用
收藏
页码：1062 / 1069
页数：8
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