Tetrathiafulvalene-containing pseudorotaxanes formed between dibenzylammonium salts and crown ethers

被引:20
作者
Ashton, PR
Becher, J
Fyfe, MCT
Nielsen, MB
Stoddart, JF
White, AJP
Williams, DJ
机构
[1] Odense Univ, Dept Chem, DK-5230 Odense M, Denmark
[2] Univ Birmingham, Sch Chem, Birmingham B15 2TT, W Midlands, England
[3] Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
[4] Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AY, England
关键词
crown ethers; dibenzylammonium salts; pseudorotaxanes; self-assembly; tetrathiafulvalene;
D O I
10.1016/S0040-4020(00)01062-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of two tetrathiafulvalene (TTF) derivatives, one carrying arms incorporating four dibenzylammonium centers and the other encompassing two annulated crown ether rings - i.e., hydrogen bond donor and acceptor functions, respectively, is described. In the presence of macrocyclic polyethers - e.g., DB24C8 and BPP34C10 - and dibenzylammonium hexafluorophosphate, these two TTF derivatives form pseudorotaxanes as evidenced by H-1 NMR spectroscopy, mass spectrometry, and differential pulse voltammetry. (C) 2001 Elsevicr Science Ltd. All rights reserved.
引用
收藏
页码:947 / 956
页数:10
相关论文
共 39 条
[11]   4-(N-METHYLTHIOAMIDO)TETRATHIAFULVALENE - A NEW KAPPA-PHASE STRUCTURE [J].
BATSANOV, AS ;
BRYCE, MR ;
COOKE, G ;
HEATON, JN ;
HOWARD, JAK .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (22) :1701-1702
[12]   1ST SYNTHESES OF AMPHIPHILIC TETRATHIAFULVANESES FROM MESOIONIC 2-PIPERIDINO-4-THIOXODITHOLES [J].
BERTHO, F ;
ROBERT, A ;
BATAIL, P ;
ROBIN, P .
TETRAHEDRON, 1990, 46 (02) :433-444
[13]  
Binet L, 1997, SYNTHESIS-STUTTGART, P1179
[14]   2-MONO OR 2,3-BIS(HYDROXYMETHYL)-6,7-ETHYLENEDITHIO-TETRATHIAFULVALENES - NEW POTENTIAL PRECURSORS OF ORGANIC METALS ENDOWED WITH HYDROGEN-BONDS [J].
BLANCHARD, P ;
SALLE, M ;
DUGUAY, G ;
JUBAULT, M ;
GORGUES, A .
TETRAHEDRON LETTERS, 1992, 33 (19) :2685-2688
[15]  
Bryce MR, 1999, ADV MATER, V11, P11, DOI 10.1002/(SICI)1521-4095(199901)11:1<11::AID-ADMA11>3.0.CO
[16]  
2-3
[17]   THE SYNTHESIS OF PRIMARY, SECONDARY AND TERTIARY AMINOMETHYLTETRATHIAFULVALENES [J].
FABRE, JM ;
GARIN, J ;
URIEL, S .
TETRAHEDRON, 1992, 48 (19) :3983-3990
[18]   A supramolecular analog of the photosynthetic special pair [J].
Feiters, MC ;
Fyfe, MCT ;
MartinezDiaz, MV ;
Menzer, S ;
Nolte, RJM ;
Stoddart, JF ;
vanKan, PJM ;
Williams, DJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (34) :8119-8120
[19]   Anion-assisted self-assembly [J].
Fyfe, MCT ;
Glink, PT ;
Menzer, S ;
Stoddart, JF ;
White, AJP ;
Williams, DJ .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (19) :2068-2070
[20]  
GIFFARD M, 1996, ADV MATER, V6, P298