Triptycene-Derived Homooxacalixarene Analogues: Synthesis, Structures, and Complexation with Fullerenes C60 and C70

被引:29
作者
Xie, Tao [1 ,2 ]
Hu, Shu-Zhen [1 ]
Chen, Chuan-Feng [1 ]
机构
[1] Chinese Acad Sci, Inst Chem, CAS Key Lab Mol Recognit & Funct, Beijing Natl Lab Mol Sci, Beijing 100190, Peoples R China
[2] Univ Chinese Acad Sci, Beijing 100049, Peoples R China
基金
中国国家自然科学基金;
关键词
CAVITY; OXACALIXARENES; CONFORMATION; EXPLORATION; ASSEMBLIES; INCLUSION; MOLECULES; DESIGN; HOST;
D O I
10.1021/jo302459m
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of triptycene-derived homooxacalixarene analogues were conveniently synthesized by a one-pot approach starting from 2,7-dihydroxytriptycene and 1,3-bisbromomethylbenzene derivatives under mild reaction conditions. Similarly, two pairs of "basket-like" triptycene-derived homooxacalixarene analogues were also designed and synthesized. Structures of these macrocyclic molecules in both solution and solid state were studied by NMR experiments and X-ray crystallography. Because of the rigid triptycene units, the homooxacalixarene analogues showed large cavities and fixed conformations even up to 380 K. It was also found that these novel macrocycles could be served as efficient host molecules for complexation with fullerenes C-60 and C-70.
引用
收藏
页码:981 / 987
页数:7
相关论文
共 57 条
[1]   New cyclic peptide assemblies with hydrophobic cavities:: The structural and thermodynamic basis of a new class of peptide nanotubes [J].
Amorín, M ;
Castedo, L ;
Granja, JR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (10) :2844-2845
[2]  
[Anonymous], 1996, COMPREHENSIVE SUPRAM
[3]  
Casnati A, 2001, CALIXARENES 2001, P365
[4]   Novel triptycene-derived hosts: synthesis and their applications in supramolecular chemistry [J].
Chen, Chuan-Feng .
CHEMICAL COMMUNICATIONS, 2011, 47 (06) :1674-1688
[5]   Synthesis, Structure, and Functionalization of Homo Heterocalix[2]arene[2]triazines: Versatile Conformation and Cavity Structures Regulated by the Bridging Elements [J].
Chen, Yin ;
Wang, De-Xian ;
Huang, Zhi-Tang ;
Wang, Mei-Xiang .
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (11) :3786-3796
[6]   THE DESIGN OF MOLECULAR HOSTS, GUESTS, AND THEIR COMPLEXES (NOBEL LECTURE) [J].
CRAM, DJ .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1988, 27 (08) :1009-1020
[7]   Methylazacalixpyridines: Remarkable bridging nitrogen-tuned conformations and cavities with unique recognition properties [J].
Gong, Han-Yuan ;
Zhang, Xiao-Hang ;
Wang, De-Xian ;
Ma, Hong-Wei ;
Zheng, Qi-Yu ;
Wang, Mei-Xiang .
CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (36) :9262-9275
[8]   Methylazacalix[4]pyridine:: En route to Zn2+-specific fluorescence sensors [J].
Gong, Han-Yuan ;
Zheng, Qi-Yu ;
Zhang, Xiao-Hang ;
Wang, De-Xian ;
Wang, Mei-Xiang .
ORGANIC LETTERS, 2006, 8 (21) :4895-4898
[9]  
Gutsche C D., 1998, Calixarenes Revisited
[10]   A heterocyclic peptide nanotube [J].
Horne, WS ;
Stout, CD ;
Ghadiri, MR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (31) :9372-9376