Rotaxane Formation from Borate Ion-Containing Crown Ether and Ammonium Ion: Enhancement of Their Association through Ion-Pairing

被引:0
|
作者
Takizawa, Takumi [1 ]
Ohtani, Kento [1 ]
Naito, Masaya [1 ]
Miyagawa, Shinobu [1 ]
Tokunaga, Yuji [1 ]
机构
[1] Univ Fukui, Fac Engn, Dept Mat Sci & Engn, Fukui 9108507, Japan
关键词
DESIGN; COMPLEXATION; BINDING;
D O I
10.1021/acs.orglett.4c03211
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We synthesized [2]rotaxanes featuring a catechol borate ion-containing crown ether and secondary ammonium ions. These rotaxane components show both ion-ion interactions and hydrogen bonds. X-ray crystallography and NMR spectroscopy allowed elucidation of the rotaxane structure. Moreover, H-1 NMR spectroscopy revealed the rotaxane synthesis can be thermodynamically controlled. The binding affinity between the borate-containing crown ether and ammonium ions is enhanced by ion-pairing.
引用
收藏
页码:8211 / 8215
页数:5
相关论文
共 50 条
  • [1] ION-PAIRING OF AMMONIUM-NITRATE IN METHANOL
    CHEN, R
    FREEMAN, GR
    JOURNAL OF PHYSICAL CHEMISTRY, 1992, 96 (17): : 7107 - 7109
  • [2] Self-sorting assembly of a calixarene/crown ether polypseudorotaxane gated by ion-pairing
    Manganaro, Nadia
    Pisagatti, Ilenia
    Notti, Anna
    Parisi, Melchiorre F.
    Gattuso, Giuseppe
    NEW JOURNAL OF CHEMISTRY, 2019, 43 (21) : 7936 - 7940
  • [3] Recent Progress in Asymmetric Ion-Pairing Catalysis with Ammonium Salts
    Qian, Deyun
    Sun, Jianwei
    CHEMISTRY-A EUROPEAN JOURNAL, 2019, 25 (15) : 3740 - 3751
  • [4] ENHANCED ENTRAPMENT OF A QUATERNARY AMMONIUM COMPOUND IN LIPOSOMES BY ION-PAIRING
    JAY, M
    DIGENIS, GA
    JOURNAL OF PHARMACEUTICAL SCIENCES, 1982, 71 (08) : 958 - 960
  • [5] Studies on the formation of hydrophobic ion-pairing complex of alendronate
    You, Sung-Kyun
    Kwon, Hae-Hyun
    Lee, Jeong-Min
    Shin, Sang-Chul
    Cho, Cheong-Weon
    ARCHIVES OF PHARMACAL RESEARCH, 2009, 32 (07) : 1055 - 1060
  • [6] Studies on the formation of hydrophobic ion-pairing complex of alendronate
    Sung-Kyun You
    Hae-Hyun Kwon
    Jeong-Min Lee
    Sang-Chul Shin
    Cheong-Weon Cho
    Archives of Pharmacal Research, 2009, 32 : 1055 - 1060
  • [7] ION-TRANSPORT THROUGH A LIQUID MEMBRANE CONTAINING CROWN ETHER
    TAKAHASHI, M
    TAKEUCHI, H
    IMANAKA, M
    KAGAKU KOGAKU RONBUNSHU, 1981, 7 (05) : 494 - 499
  • [8] ENHANCEMENT OF PROTEIN LIPOPHILICITY AND STABILITY VIA HYDROPHOBIC ION-PAIRING
    MATSUURA, J
    POWERS, ME
    MANNING, MC
    SHEFTER, E
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1993, 205 : 61 - BIOT
  • [9] Ion-containing membranes from microemulsion polymerization
    Chow, PY
    Chew, CH
    Ong, CL
    Wang, J
    Xu, G
    Gan, LM
    LANGMUIR, 1999, 15 (09) : 3202 - 3205
  • [10] SPECTROSCOPIC AND CONFIGURATIONAL ASSIGNMENTS FROM ION-PAIRING EFFECTS
    MASON, SF
    NORMAN, BJ
    CHEMICAL COMMUNICATIONS, 1965, (05) : 73 - &