Triptycene-Derived N(H)-Bridged Azacalixarenes: Synthesis, Structure, and Encapsulation of Small Neutral Molecules in the Solid State

被引:58
作者
Xue, Min [1 ,2 ]
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] Chinese Acad Sci, Grad Sch, Beijing 100049, Peoples R China
基金
中国国家自然科学基金;
关键词
CRYSTAL-STRUCTURE; COMPLEXATION; HOST; CAVITY; ETHER; RECOGNITION;
D O I
10.1021/ol902246c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Four pairs of novel N(H)-bridged azacalixarenes derived from triptycene were synthesized by both one-pot and two-step fragment-coupling approaches. Due to the unique 3D rigid structure of triptycene, the macrocycles all adopted fixed conformations in both solution and solid state. X-ray crystallographic analyses also revealed that the cis isomers with boat conformations showed the capability of encapsulating methanol and acetone molecules inside.
引用
收藏
页码:5294 / 5297
页数:4
相关论文
共 39 条
[1]   Azacalix[n]arenes with -NH- amino group:: NH•••OCH3 interaction-assisted synthesis, structure, and reactivity [J].
Fukushima, W ;
Kanbara, T ;
Yamamoto, T .
SYNLETT, 2005, (19) :2931-2934
[2]   Highly selective recognition of diols by a self-regulating fine-tunable methylazacalix[4]pyridine cavity: Guest-dependent formation of molecular-sandwich and molecular-capsule complexes in solution and the solid state [J].
Gong, Han-Yuan ;
Wang, De-Xian ;
Xiang, Jun-Feng ;
Zheng, Qi-Yu ;
Wang, Mei-Xiang .
CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (27) :7791-7802
[3]   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
[4]  
GUTSCHE CD, 2008, CALIXARENES INTRO, P45
[5]   A triptycene-based bis(crown ether) host: Complexation with both paraquat derivatives and dibenzylammonium salts [J].
Han, T ;
Chen, CF .
ORGANIC LETTERS, 2006, 8 (06) :1069-1072
[6]   Azacalix[4] arene cation radicals:: spin-delocalised doublet- and triplet-ground states observed in the macrocyclic m-phenylene system connected with nitrogen atoms [J].
Ishibashi, Koichi ;
Tsue, Hirohito ;
Sakai, Naoko ;
Tokita, Satoshi ;
Matsui, Kazuhiro ;
Yamauchi, Jun ;
Tamura, Rui .
CHEMICAL COMMUNICATIONS, 2008, (24) :2812-2814
[7]   Regioselectively N-methylated azacalix[8]arene octamethyl ether prepared by catalytic aryl amination reaction using a temporal N-silylation protocol [J].
Ishibashi, Koichi ;
Tsue, Hirohito ;
Tokita, Satoshi ;
Matsui, Kazuhiro ;
Takahashi, Hiroki ;
Tamura, Rui .
ORGANIC LETTERS, 2006, 8 (26) :5991-5994
[8]   Tetraaza[1.1.1.1]metacyclophane [J].
Ito, A ;
Ono, Y ;
Tanaka, K .
NEW JOURNAL OF CHEMISTRY, 1998, 22 (08) :779-781
[9]   N-methyl-substituted aza[1n]metacyclophane:: Preparation, structure, and properties [J].
Ito, A ;
Ono, Y ;
Tanaka, A .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (22) :8236-8241
[10]   An N-substituted aza[14] metacyclophane tetracation:: a spin-quintet tetraradical with four para-phenylenediamine-based semi-quinone moieties [J].
Ito, Akihiro ;
Inoue, Syuuzi ;
Hirao, Yasukazu ;
Furukawa, Ko ;
Kato, Tatsuhisa ;
Tanaka, Kazuyoshi .
CHEMICAL COMMUNICATIONS, 2008, (28) :3242-3244