Synthesis and characterization of a persistent paramagnetic rotaxane based on α-cyclodextrin

被引：32
|
作者：
Mezzina, E [1 ]
Fanì, M [1 ]
Ferroni, F [1 ]
Franchi, P [1 ]
Menna, M [1 ]
Lucarini, M [1 ]
机构：
[1] Univ Bologna, Dept Organ Chem A Mangini, I-40126 Bologna, Italy
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 71卷 / 10期
关键词：
D O I：
10.1021/jo0601720
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The synthesis and spectroscopic properties of a novel paramagnetic [2]rotaxane is described. This rotaxane is made from molecules having an alkyl chain flanked by 2,2,6,6-tetramethylpiperidine-N-oxyl (TEMPO) groups. Complexation of sebacoyl chloride by R-cyclodextrin followed by reaction with a bulky aminonitroxide resulted in the trapping of the cyclodextrin, threaded by the alkyl chain, thus generating the rotaxane structure. The structure of the paramagnetic [2]rotaxane was fully characterized by ESIMS, 1D and 2D NMR and ESR spectroscopy.
引用
收藏
页码：3773 / 3777
页数：5
相关论文
共 50 条
  • [21] Synthesis of a Structure-Definite α-Cyclodextrin-Based Macromolecular [3]Rotaxane Using a Size-Complementary Method
    Akae, Yosuke
    Sogawa, Hiromitsu
    Takata, Toshikazu
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (36) : 11742 - 11746
  • [22] Synthesis and characterization of poly(ethylene glycol) based β-cyclodextrin polymers
    Nielsen, Thorbjorn Terndrup
    Wintgens, Veronique
    Larsen, Kim Lambertsen
    Amiel, Catherine
    JOURNAL OF INCLUSION PHENOMENA AND MACROCYCLIC CHEMISTRY, 2009, 65 (3-4) : 341 - 348
  • [23] Synthesis and characterization of poly(ethylene glycol) based β-cyclodextrin polymers
    Thorbjørn Terndrup Nielsen
    Véronique Wintgens
    Kim Lambertsen Larsen
    Catherine Amiel
    Journal of Inclusion Phenomena and Macrocyclic Chemistry, 2009, 65 : 341 - 348
  • [24] Synthesis and characterization of mannosyl mimetic derivatives based on a β-cyclodextrin core
    Yockot, D
    Moreau, V
    Demailly, G
    Djedaïni-Pilard, F
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (10) : 1810 - 1818
  • [25] β-cyclodextrin polymer brushes based on hyperbranched polycarbosilane:: Synthesis and characterization
    Tian, Wei
    Fan, Xiao-Dong
    Liu, Yu-Yang
    Jiang, Min
    Huang, Yi
    Kong, Jie
    JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2008, 46 (15) : 5036 - 5052
  • [26] Synthesis of Ferrocene-Cyclodextrin, Anthracene-Cyclodextrin, and Pyrene-Cyclodextrin [2]Rotaxane Conjugates and Their Intercomponent Behavior as Observed in NMR Spectroscopy
    Tumaneng, John Vincent
    Matulac, Andrea Louise
    Reyes, Jude
    Baldovino, Amyel Joseph
    Lumba, Joseph
    Yu, Gilbert
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 11 (12)
  • [27] Synthesis and characterization of amino derivatives of persistent trityl radicals as dual function pH and oxygen paramagnetic probes
    Dhimitruka, Ilirian
    Bobko, Andrey A.
    Hadad, Christopher M.
    Zweier, Jay L.
    Khramtsov, Valery V.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (32) : 10780 - 10787
  • [28] Synthesis and characterization of amino derivatives of persistent trityl radicals as dual function pH and oxygen paramagnetic probes
    Dhimitruka, Ilirian
    Bobko, Andrey A.
    Hadad, Christopher M.
    Zweier, Jay L.
    Khramtsov, Valery V.
    Journal of the American Chemical Society, 2008, 130 (32): : 10780 - 10787
  • [29] Pillar[5]arene-Based [2]Rotaxane: Synthesis, Characterization, and Application in a Coupling Reaction
    Guo, Hao
    Ye, Junmei
    Zhang, Zhecheng
    Wang, Yang
    Yuan, Xiaolei
    Ou, Changjin
    Ding, Yue
    Yan, Chaoguo
    Wang, Jin
    Yao, Yong
    INORGANIC CHEMISTRY, 2020, 59 (17) : 11915 - 11919
  • [30] Increasing the persistency of stable free-radicals: Synthesis and characterization of a nitroxide based [1]rotaxane
    Franchi, Paola
    Fani, Michela
    Mezzina, Elisabetta
    Lucarini, Marco
    ORGANIC LETTERS, 2008, 10 (10) : 1901 - 1904
12345