A colorimetric anion sensing system utilising competitive C-H•••X- hydrogen bonding

被引:5
|
作者
Sato, Kiyoshi [1 ]
Okabe, Yuko [1 ]
Onitake, Tomomi [1 ]
Yamaguchi, Motowo [1 ]
Arai, Sadao [2 ]
Yamagishi, Takamichi [1 ]
机构
[1] Tokyo Metropolitan Univ, Grad Sch Urban Environm Sci, Dept Appl Chem, Tokyo 1920397, Japan
[2] Tokyo Med Univ, Dept Chem, Shinjyuku Ku, Tokyo, Japan
关键词
anion recognition; imidazolium; competitive binding; C-H hydrogen bonding; colorimetric anion sensing; DYES; INDICATORS; RECEPTORS; COMPLEXES; LEADS; RING;
D O I
10.1080/10610278.2010.521839
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Combination of tripodal imidazolium-based anion receptor 1 and azonia betaine dye 2 has enabled a colorimetric detection of halide ions by competitive binding. The imidazolium groups of receptor 1 interact with the phenoxy oxygen of betaine dye 2 in acetonitrile solution by multiple [C-H...O-] hydrogen bonds. Consequently, the blue-coloured solution of the dye immediately turns to greenish yellow upon addition of receptor 1 due to the receptor-dye complex formation. The reversed colour change, which is caused by displacement of guests, is observed by the addition of Cl-, Br- or I- anions to the receptor-dye complex solution.
引用
收藏
页码:249 / 251
页数:3
相关论文
共 50 条
  • [1] Nonspherical anion sequestration by C-H hydrogen bonding
    Mirzaei, Saber
    Espinoza Castro, Victor M.
    Hernandez Sanchez, Raul
    CHEMICAL SCIENCE, 2022, 13 (07) : 2026 - 2032
  • [2] Intramolecular C-H•••O Hydrogen Bonding-Driven 1,2,3-Trazole Foldamers: Assessment of Intermolecular C-H•••X-(X=Cl, Br, I) and C-H•••N Hydrogen Bonding
    Sun, Guangjun
    Nie, Chengbin
    Zhao, Xin
    Li, Zhanting
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2017, 37 (07) : 1757 - 1763
  • [3] Importance of aliphatic C-H hydrogen bonding on anion recognition
    Sohn, Dae Hyup
    Han, Eunbi
    Park, Jong Il
    Cho, Seung Joo
    Kang, Jongmin
    SUPRAMOLECULAR CHEMISTRY, 2018, 30 (03) : 169 - 178
  • [4] Aryl C-H•••Cl- hydrogen bonding in a fluorescent anion sensor
    Tresca, Blakely W.
    Zakharov, Lev N.
    Carroll, Calden N.
    Johnson, Darren W.
    Haley, Michael M.
    CHEMICAL COMMUNICATIONS, 2013, 49 (65) : 7240 - 7242
  • [5] Novel Ionophores with 2n-Crown-n Topology: Anion Sensing via Pure Aliphatic C-H•••Anion Hydrogen Bonding
    Shi, Genggongwo
    Gadhe, Changdev G.
    Park, Sung-Woo
    Kim, Kwang S.
    Kang, Jongmin
    Seema, Humaira
    Singh, N. Jiten
    Cho, Seung Joo
    ORGANIC LETTERS, 2014, 16 (02) : 334 - 337
  • [6] Octa-amidocavitand: Paired Anion Binding through N-H•••X- and C-H•••X- Interactions
    Jung, Nak Shin
    Lee, Jaeok
    Suh, Sungjong
    Paek, Kyungsoo
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2009, 30 (11): : 2782 - 2784
  • [7] Phosphinate selective hosts and importance of C-H hydrogen bonding for affinity modulation toward anion guests
    Sohn, Dae Hyup
    Han, Eunbi
    Cho, Seung Joo
    Kang, Jongmin
    TETRAHEDRON LETTERS, 2018, 59 (18) : 1728 - 1732
  • [8] Aromatic Triazole Foldamers Induced by C-H•••X (X = F, Cl) Intramolecular Hydrogen Bonding
    Shang, Jie
    Gallagher, Nolan M.
    Bie, Fusheng
    Li, Qiaolian
    Che, Yanke
    Wang, Ying
    Jiang, Hua
    JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (11) : 5134 - 5144
  • [9] Novel heterocyclic thiosemicarbazones derivatives as colorimetric and "turn on" fluorescent sensors for fluoride anion sensing employing hydrogen bonding
    Kumar, S. L. Ashok
    Kumar, M. Saravana
    Sreeja, P. B.
    Sreekanth, A.
    SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 2013, 113 : 123 - 129
  • [10] Solution and solid-phase halogen and C-H hydrogen bonding to perrhenate
    Massena, Casey J.
    Riel, Asia Marie S.
    Neuhaus, George F.
    Decato, Daniel A.
    Berryman, Orion B.
    CHEMICAL COMMUNICATIONS, 2015, 51 (08) : 1417 - 1420