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
收藏
页码:3556 / 3565
页数:10
相关论文
共 50 条
  • [1] Highly Stereoselective Recognition and Deracemization of Amino Acids by Supramolecular Self-Assembly
    So, Soon Mog
    Moozeh, Kimia
    Lough, Alan J.
    Chin, Jik
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (03) : 829 - 832
  • [2] Enantioselective recognition of amino acids by chiral peptido-calix[4]arenes and thiacalix[4]arenes
    Bois, Joackim
    Bonnamour, Isabelle
    Duchamp, Christian
    Parrot-Lopez, Helene
    Darbost, Ulrich
    Felix, Caroline
    [J]. NEW JOURNAL OF CHEMISTRY, 2009, 33 (10) : 2128 - 2135
  • [3] Facile route to supramolecular structures:: Self-assembly of dendrimers and naphthalene dicarboxylic acids
    Groehn, Franziska
    Klein, Katja
    Brand, Sabrina
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (23) : 6866 - 6869
  • [4] Straight from the bottle! Wine and juice dicarboxylic acids as templates for supramolecular cage self-assembly
    Begato, Federico
    Penasa, Roberto
    Licini, Giulia
    Zonta, Cristiano
    [J]. CHEMICAL COMMUNICATIONS, 2021, 57 (78) : 10019 - 10022
  • [5] Impact of amino acids on the aqueous self-assembly of benzenetrispeptides into supramolecular polymer bottlebrushes
    Klein, Tobias
    Ulrich, Hans F.
    Gruschwitz, Franka V.
    Kuchenbrod, Maren T.
    Takahashi, Rintaro
    Fujii, Shota
    Hoeppener, Stephanie
    Nischang, Ivo
    Sakurai, Kazuo
    Brendel, Johannes C.
    [J]. POLYMER CHEMISTRY, 2020, 11 (42) : 6763 - 6771
  • [6] The self-assembly of catenated calix[4]arenes
    Li, ZT
    Ji, GZ
    Yuan, SD
    Du, AL
    Ding, H
    Wei, M
    [J]. TETRAHEDRON LETTERS, 1998, 39 (36) : 6517 - 6520
  • [7] Multi-functional imidazolium dendrimers based on thiacalix[4]arenes: self-assembly, catalysis and DNA binding
    Sultanova, Elza D.
    Fedoseeva, Angelina A.
    Fatykhova, Aigul M.
    Mironova, Diana A.
    Ziganshina, Sufia A.
    Ziganshin, Marat A.
    Evtugyn, Vladimir G.
    Burilov, Vladimir A.
    Solovieva, Svetlana E.
    Antipin, Igor S.
    [J]. SOFT MATTER, 2024, 20 (35) : 7072 - 7082
  • [8] Sulfobetaine derivatives of thiacalix[4]arene: synthesis and supramolecular self-assembly of submicron aggregates with AgI cations
    Yakimova, Luidmila S.
    Padnya, Pavel L.
    Kunafina, Aisylu F.
    Nugmanova, Aigul R.
    Stoikov, Ivan I.
    [J]. MENDELEEV COMMUNICATIONS, 2019, 29 (01) : 86 - 88
  • [9] Self-Assembly of Supramolecular Architectures by the Effect of Amino Acid Residues of Quaternary Ammonium Pillar[5]arenes
    Nazarova, Anastasia
    Shurpik, Dmitriy
    Padnya, Pavel
    Mukhametzyanov, Timur
    Cragg, Peter
    Stoikov, Ivan
    [J]. INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, 2020, 21 (19) : 1 - 19
  • [10] Supramolecular Self-assembly and Functionalization of Porphyrin-based Systems
    许良
    李勇军
    [J]. 结构化学, 2014, 33 (03) : 367 - 386