Adjustable chiral self-sorting and self-discriminating behaviour between diamond-like Tröger's base-linked cryptands

作者: Yuan Chen , Cheng Qian , Qian Zhao , Ming Cheng , Xinran Dong

DOI: 10.1039/C9CC03577J

关键词:

摘要: Two isomers of Troger's base-linked cryptands 5a and 5b were synthesized, both them have two chiral N-centers, exhibiting rare diamond-like scaffolds. Particularly, when growing from the solution rac-5a, a single enantiomer RNRN-5a was found in crystal cell, revealing self-sorting behaviour. However, adding CF3COOH to protonate base enantiomers formed pairs self-discriminating

参考文章(52)
Sundus Erbas-Cakmak, David A. Leigh, Charlie T. McTernan, Alina L. Nussbaumer, Artificial Molecular Machines Chemical Reviews. ,vol. 115, pp. 10081- 10206 ,(2015) , 10.1021/ACS.CHEMREV.5B00146
Chuyang Cheng, Paul R. McGonigal, Severin T. Schneebeli, Hao Li, Nicolaas A. Vermeulen, Chenfeng Ke, J. Fraser Stoddart, An artificial molecular pump Nature Nanotechnology. ,vol. 10, pp. 547- 553 ,(2015) , 10.1038/NNANO.2015.96
Julius Tröger, Ueber einige mittelst nascirenden Formaldehydes entstehende Basen Journal Fur Praktische Chemie-chemiker-zeitung. ,vol. 36, pp. 225- 245 ,(1887) , 10.1002/PRAC.18870360123
Josep Artacho, Erhad Ascic, Toni Rantanen, Carl-Johan Wallentin, Sami Dawaigher, Karl-Erik Bergquist, Michael Harmata, Victor Snieckus, Kenneth Wärnmark, Tröger’s Base Twisted Amides: Endo Functionalization and Synthesis of an Inverted Crown Ether Organic Letters. ,vol. 14, pp. 4706- 4709 ,(2012) , 10.1021/OL302022Y
Bohumil Dolenský, Martin Havlík, Vladimír Král, Oligo Tröger's bases—new molecular scaffolds Chemical Society Reviews. ,vol. 41, pp. 3839- 3858 ,(2012) , 10.1039/C2CS15307F
U. Kiehne, T. Weilandt, A. Lützen, Diastereoselective self-assembly of double-stranded helicates from Tröger's base derivatives. Organic Letters. ,vol. 9, pp. 1283- 1286 ,(2007) , 10.1021/OL070048I
Carolyn Pratt Brock, W. Bernd Schweizer, Jack D. Dunitz, On the validity of Wallach's rule: on the density and stability of racemic crystals compared with their chiral counterparts Journal of the American Chemical Society. ,vol. 113, pp. 9811- 9820 ,(1991) , 10.1021/JA00026A015
Grégorio Crini, Review: A history of cyclodextrins Chemical Reviews. ,vol. 114, pp. 10940- 10975 ,(2014) , 10.1021/CR500081P
Min Xue, Yong Yang, Xiaodong Chi, Xuzhou Yan, Feihe Huang, Development of Pseudorotaxanes and Rotaxanes: From Synthesis to Stimuli-Responsive Motions to Applications Chemical Reviews. ,vol. 115, pp. 7398- 7501 ,(2015) , 10.1021/CR5005869
Koji Kano, Hitoshi Matsumoto, Shizunobu Hashimoto, Masahiko Sisido, Yukio Imanishi, A chiral pyrene excimer in .gamma.-cyclodextrin cavity Journal of the American Chemical Society. ,vol. 107, pp. 6117- 6118 ,(1985) , 10.1021/JA00307A055