Supramolecular "containers": self-assembly and functionalization of thiacalix[4]arenes for recognition of amino- and dicarboxylic acids

被引:40
|
作者
Andreyko, Elena A. [1 ]
Padnya, Pavel L. [1 ]
Daminova, Rozalina R. [1 ]
Stoikov, Ivan I. [1 ]
机构
[1] Kazan Volga Reg Fed Univ, AM Butlerov Chem Inst, Kazan 420008, Russia
关键词
P-TERT-BUTYL; LOWER RIM; COMPLEXATION PROPERTIES; MOLECULAR CAPSULES; COPPER-COMPLEXES; HYDRAZIDE GROUPS; METAL-CATIONS; AMIDE GROUPS; RECEPTORS; BINDING;
D O I
10.1039/c3ra44052d
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
New p-tert-butylthiacalix[4]arenes containing amide, tertiary amine and ammonium fragments in cone conformation were synthesized and characterized. The interaction of the p-tert-butylthiacalix[4]arenes with amino-, dicarboxylic acids and EDTA was studied by electron spectroscopy. The ability of the synthesized thiacalix[4]arenes to form supermolecules and supramolecular associates with guests was shown by dynamic light scattering. The formation of commutative and cascade supramolecular systems based on amphiphilic macrocycles was studied by UV spectroscopy and dynamic light scattering. It was shown that thiacalix[4]arene containing quaternary ammonium fragments with three methyl groups at the nitrogen form associates - "containers" containing glutamic acid as a guest.
引用
下载
收藏
页码:3556 / 3565
页数:10
相关论文
共 50 条
  • [21] Manipulation of Hierarchical Chiral Self-assembly and Anion Recognition by Supramolecular Systems of ß-Glucopyranoside, Pillar[5]arenes, and Polyoxometalates
    Zeng, Mengyan
    Chen, Xin
    Zhang, Jie
    CHEMISTRY-A EUROPEAN JOURNAL, 2023, 29 (60)
  • [22] Supramolecular self-assembly of d(TGG)(4).
    Chen, FM
    BIOPHYSICAL JOURNAL, 1997, 72 (02) : TH443 - TH443
  • [23] Anion-Based Self-assembly of Resorcin[4]arenes and Pyrogallol[4]arenes
    Chwastek, Monika
    Cmoch, Piotr
    Szumna, Agnieszka
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2022, 144 (12) : 5350 - 5358
  • [24] Self-Assembly Evolution of N-Terminal Aromatic Amino Acids with Transient Supramolecular Chirality
    Xue, Shixin
    Zhang, Nan
    Hu, Xiaoling
    Zeng, Yongfei
    Zhang, Jingbo
    Xing, Pengyao
    Zhao, Yanli
    JOURNAL OF PHYSICAL CHEMISTRY LETTERS, 2020, 11 (04): : 1490 - 1496
  • [25] Phosphorylated amino derivatives of thiacalix [4] arene as membrane carriers: synthesis and host-guest molecular recognition of amino, hydroxy and dicarboxylic acids
    Mostovaya, Olga A.
    Agafonova, Maria N.
    Galukhin, Andrey V.
    Khayrutdinov, Bulat I.
    Islamov, Daut
    Kataeva, Olga N.
    Antipin, Igor S.
    Konovalov, Alexander I.
    Stoikov, Ivan I.
    JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 2014, 27 (01) : 57 - 65
  • [26] Self-assembly of p-tert-butyl thiacalix[4]arenes and metal cations into nanoscale three-dimensional particles
    Stoikov, Ivan I.
    Yushkova, Elena A.
    Bukharaev, Anastas A.
    Biziaev, Dmitry A.
    Selivanovskaya, Svetlana Yu
    Chursina, Mariya A.
    Antipin, Igor S.
    Konovalov, Alexander I.
    Zharov, Ilya
    JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 2012, 25 (12) : 1177 - 1185
  • [27] Supramolecular approaches to the formation of nanostructures based on phosphonate-thiacalix[4]arenes, their selective lysozyme recognition
    Yakimova, Luidmila
    Vavilova, Alena
    Shibaeva, Ksenia
    Sultanaev, Vildan
    Mukhametzyanov, Timur
    Stoikov, Ivan
    COLLOIDS AND SURFACES A-PHYSICOCHEMICAL AND ENGINEERING ASPECTS, 2021, 611
  • [28] Molecular recognition. Electrostatic effects in supramolecular self-assembly
    Crowley, JD
    Goshe, AJ
    Bosnich, B
    CHEMICAL COMMUNICATIONS, 2003, (03) : 392 - 393
  • [29] Dendrimers in supramolecular chemistry: From molecular recognition to self-assembly
    Zeng, FW
    Zimmerman, SC
    CHEMICAL REVIEWS, 1997, 97 (05) : 1681 - 1712
  • [30] MOLECULAR-RECOGNITION-DIRECTED SELF-ASSEMBLY OF SUPRAMOLECULAR POLYMERS
    PERCEC, V
    HECK, J
    JOHANSSON, G
    TOMAZOS, D
    KAWASUMI, M
    UNGAR, G
    JOURNAL OF MACROMOLECULAR SCIENCE-PURE AND APPLIED CHEMISTRY, 1994, A31 (08): : 1031 - 1070