Encapsulation of tetramethylphosphonium cations

被引:25
作者
Beyeh, Ngong Kodiah [1 ]
Valkonen, Arto [1 ]
Rissanen, Kari [1 ]
机构
[1] Univ Jyvaskyla, Dept Chem, Nanosci Ctr, Jyvaskyla, Finland
关键词
supramolecular chemistry; resorcinarenes; capsules; X-ray crystallography; mass spectrometry; HOST-GUEST CHEMISTRY; GAS-PHASE; REVERSIBLE ENCAPSULATION; MOLECULAR RECOGNITION; SUPRAMOLECULAR CHEMISTRY; C-METHYL; RESORCINARENE; AMMONIUM; CAPSULES; COMPLEXATION;
D O I
10.1080/10610270802308411
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The weak interactions and capsule formation of tetramethylphosphonium (TMP) cation with resorcinarenes 1 and 2 and the corresponding pyrogallarenes 3 and 4 were studied in the solid state by single-crystal X-ray diffraction, in solution by NMR and in the gas phase by mass spectrometry. In methanol-d4, the NMR titration studies reveal that the association constants for the 1:1 complexes of TMP@3 and TMP@4 are much higher (TMP@4:39037 M-1) than for the corresponding TMP@1 and TMP@2 (TMP@2:13010 M-1) complexes. In the gas phase both monomeric 1:1 TMP@1-TMP@4 complexes as well as the dimeric 1:2 capsule complexes, TMP@12-TMP@42 were observed. The 1:1:2 molar mixtures of 1:2:TMP or 3:4:TMP resulted in homo- and heterocapsules TMP@12, TMP@1+2 and TMP@22, with the expected statistical 1:2:1 ratio. Using the 1:1:2 ratio of 1:3:TMP, 1:4:TMP, 2:3:TMP or 2:4:TMP showed a marked prefence to the homopyrogallarene capsules TMP@32 and TMP@42, thus supporting the stronger complexation of TMP with 3 and 4 as observed in solution. The X-ray structures1 confirmed the dimeric capsular structures with only minor structural differences to the corresponding tetramethylammonium (TMA) capsules reported earlier.
引用
收藏
页码:142 / 148
页数:7
相关论文
共 80 条
[1]   Derivatisation of pyrogallarenes [J].
Åhman, A ;
Luostarinen, M ;
Schalley, CA ;
Nissinen, M ;
Rissanen, K .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (13) :2793-2801
[2]   Complexation of C-methyl pyrogallarene with small quaternary and tertiary alkyl ammonium cations [J].
Ahman, Antti ;
Luostarinen, Minna ;
Rissanen, Kari ;
Nissinen, Maija .
NEW JOURNAL OF CHEMISTRY, 2007, 31 (01) :169-177
[3]   Cation-pi interactions between neutral calix[5]arene hosts and cationic organic guests [J].
Arnecke, R ;
Bohmer, V ;
Cacciapaglia, R ;
Cort, AD ;
Mandolini, L .
TETRAHEDRON, 1997, 53 (13) :4901-4908
[4]  
Atwood J.L., 2002, J. Supramol. Chem., V2, P479, DOI [10.1016/S1472-7862(03)00068-6, DOI 10.1016/S1472-7862(03)00068-6]
[5]   Guest transport in a nonporous organic solid via dynamic van der Waals cooperativity [J].
Atwood, JL ;
Barbour, LJ ;
Jerga, A ;
Schottel, BL .
SCIENCE, 2002, 298 (5595) :1000-1002
[6]   Hydrogen bonds seal single-molecule capsules [J].
Atwood, JL ;
Szumna, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (36) :10646-10647
[7]   PURIFICATION OF C-60 AND C-70 BY SELECTIVE COMPLEXATION WITH CALIXARENES [J].
ATWOOD, JL ;
KOUTSANTONIS, GA ;
RASTON, CL .
NATURE, 1994, 368 (6468) :229-231
[8]   Storage of methane and freon by interstitial van der Waals confinement [J].
Atwood, JL ;
Barbour, LJ ;
Jerga, A .
SCIENCE, 2002, 296 (5577) :2367-2369
[9]   Hydrogen-bonded molecular capsules are stable in polar media [J].
Atwood, JL ;
Barbour, LJ ;
Jerga, A .
CHEMICAL COMMUNICATIONS, 2001, (22) :2376-2377
[10]   Synthesis of chiral resorcinarene-based hosts and a mass spectrometric study of their chemistry in solution and the gas phase [J].
Beyeh, Ngong K. ;
Feher, Domonkos ;
Luostarinen, Minna ;
Schalley, Christoph A. ;
Rissanen, Kari .
JOURNAL OF INCLUSION PHENOMENA AND MACROCYCLIC CHEMISTRY, 2006, 56 (3-4) :381-394