Synthesis and optical characterization of novel azacrown ethers containing an acridinone or an N-methylacridinone unit as potential fluorescent chemosensors

被引：38
|
作者：
Moczar, Ildiko [1 ]
Huszthy, Peter [1 ,2 ]
Mezei, Andras [3 ]
Kadar, Mihaly [4 ,5 ]
Nyitrai, Jozsef [2 ]
Toth, Klara [3 ,4 ]
机构：
[1] Hungarian Acad Sci, Res Grp Alkaloid Chem, H-1521 Budapest, Hungary
[2] Budapest Univ Technol & Econ, Dept Organ Chem & Technol, H-1521 Budapest, Hungary
[3] Budapest Univ Technol & Econ, Dept Inorgan & Analyt Chem, H-1521 Budapest, Hungary
[4] Hungarian Acad Sci, Res Grp Tech Analyt Chem, H-1521 Budapest, Hungary
[5] Chinoin Chem & Pharmaceut Works Ltd, H-1325 Budapest, Hungary
来源：
TETRAHEDRON | 2010年 / 66卷 / 01期
基金：
匈牙利科学研究基金会;
关键词：
Azacrown ethers; Acridinones; Chiral crown ethers; Fluorescent chemosensors; Cation recognition; Enantiomeric recognition; ENANTIOMERIC RECOGNITION; CROWN-ETHERS; ENANTIOSELECTIVE RECOGNITION; COMPLEXATION BEHAVIOR; SELECTIVE DETECTION; ALKALINE-EARTH; SENSORS; METAL; SAXITOXIN; BINDING;
D O I：
10.1016/j.tet.2009.10.076
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Four new achiral and four new chiral monoazacrown ethers containing an acridinone or an N-methylacridinone fluorescent signalling unit were prepared by reacting chloromethyl-substituted acridinone derivatives with achiral monoazacrown ethers with different cavity sizes and enantiopure monoaza-18-crown-6 ethers having two methyl and two isobutyl groups on their chiral centres, respectively. The operation of these chemosensors is based on the photoinduced electron transfer (PET) process, thus they show fluorescence enhancement in the presence of cationic guests. Their fluorescent behaviour as well as their complexation properties towards selected metal ions and the enantiomers of alpha-(1-naphthyl)-ethylammonium perchlorate and potassium mandelate were examined. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码：350 / 358
页数：9
相关论文
共 12 条
  • [1] Synthesis and optical characterization of novel enantiopure BODIPY linked azacrown ethers as potential fluorescent chemosensors
    Moczar, Ildiko
    Huszthy, Peter
    Maidics, Zita
    Kadar, Mihaly
    Toth, Klara
    TETRAHEDRON, 2009, 65 (39) : 8250 - 8258
  • [2] Synthesis and fluorescence studies of novel bis(azacrown ether) type chemosensors containing an acridinone unit
    Moczar, Ildiko
    Peragovics, Agnes
    Baranyai, Peter
    Toth, Klara
    Huszthy, Peter
    TETRAHEDRON, 2010, 66 (16) : 2953 - 2960
  • [3] Fluorescent chemosensors containing ruthenium(II) bipyridine as fluorogenic unit and modified calix[4]arene as ionophore: Synthesis, characterization, electrochemistry and ion-binding property
    Patra, Subrata
    Boricha, Vinod P.
    Paul, Parimal
    INORGANICA CHIMICA ACTA, 2022, 539
  • [4] Synthesis and characterization of a novel kind soluble, conjugated, and fluorescent chelate polymer containing fluorene ring in the backbone: Optical, electrical, and electrochemical properties
    Yildirim, Mehmet
    Kaya, Ismet
    SYNTHETIC METALS, 2011, 161 (1-2) : 13 - 22
  • [5] Synthesis and characterization of potential NO donors:: novel iron-sulfur nitrosyls containing the μ-N-C-S skeleton
    Rakova, OA
    Sanina, NA
    Aldoshin, SM
    Goncharova, NV
    Shilov, GV
    Shulga, YM
    Ovanesyan, NS
    INORGANIC CHEMISTRY COMMUNICATIONS, 2003, 6 (02) : 145 - 148
  • [6] When crown ethers finally click: novel, click-assembled, fluorescent enantiopure pyridino-crown ether-based chemosensors - and an N-2-aryl-1,2,3-triazole containing one
    Szemenyei, Balazs
    Malmosi, Mira
    Pal, David
    Baranyai, Peter
    Drahos, Laszlo
    Moczar, Ildiko
    Huszthy, Peter
    NEW JOURNAL OF CHEMISTRY, 2021, 45 (48) : 22639 - 22649
  • [7] Synthesis, characterization and polymerization potential of ansa-metallocene dichloride complexes of titanium, zirconium and hafnium containing a Si-N-Si bridging unit
    Alt, HG
    Fottinger, K
    Milius, W
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1998, 564 (1-2) : 109 - 114
  • [8] Novel levofloxacin zinc (II) complexes with N-donor heterocyclic ligands, as potential fluorescent probes for cell imaging: Synthesis, structural characterization and in vitro cytotoxicity
    Galani, Anastasia
    Efthimiadou, Eleni K.
    Theodosiou, Theodosis
    Kordas, George
    Karaliota, Alexandra
    INORGANICA CHIMICA ACTA, 2014, 423 : 52 - 59
  • [9] Synthesis, characterization and optical properties of novel dendronized azo-dyes containing a fullerene C60 unit and well-defined oligo(ethylene glycol) segments
    Ortiz-Palacios, Jesus
    Zaragoza-Galan, Gerardo
    Aguilar-Ortiz, Edgar
    Rodriguez-Alba, Efrain
    Rivera, Ernesto
    RSC ADVANCES, 2017, 7 (27): : 16751 - 16762
  • [10] Synthesis, Characterization and Potential Electrochemical Properties of Novel Mn-Re Dinuclear Complexes Containing N-Heterocyclic Carbene-carbon Disulfide Ligands
    Zhao Jia
    Sun Huabing
    Liu Lingyan
    Chang Weixing
    Li Jing
    CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE, 2014, 35 (01): : 68 - 74
12