Synthesis and evaluation of a novel fluorescent sensor based on hexahomotrioxacalix[3]arene for Zn2+ and Cd2+

被引:16
作者
Jiang, Xue-Kai [1 ]
Ikejiri, Yusuke [1 ]
Jin, Cheng-Cheng [1 ]
Wu, Chong [1 ]
Zhao, Jiang-Lin [1 ]
Ni, Xin-Long [2 ]
Zeng, Xi [2 ]
Redshaw, Carl [3 ]
Yamato, Takehiko [1 ]
机构
[1] Saga Univ, Fac Sci & Engn, Dept Appl Chem, Honjo Machi 1, Saga 8408502, Japan
[2] Guizhou Univ, Key Lab Macrocycl & Supramol Chem Guizhou Prov, Guiyang 550025, Guizhou, Peoples R China
[3] Univ Hull, Dept Chem, Cottingham Rd, Kingston Upon Hull HU6 7RX, Yorks, England
基金
英国工程与自然科学研究理事会;
关键词
Hexahomotrioxacalix[3]arene; Metal ion recognition; Pyrenyl-appended triazole; Fluorescent sensor; Zinc cation; CLICK CHEMISTRY; INCLUSION PROPERTIES; IONS; RECOGNITION; DERIVATIVES; RECEPTORS; CHEMOSENSOR; DESIGN; CU2+; GLYCOCLUSTERS;
D O I
10.1016/j.tet.2016.06.055
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel type of selective and sensitive fluorescent sensor having triazole rings as the binding sites on the lower rim of a hexahomotrioxacalix[3]arene scaffold in a cone conformation is reported. This sensor has desirable properties for practical applications, including selectivity for detecting Zn2+ and Cd2+ in the presence of excess competing metal ions at low ion concentration or as a fluorescence enhancement type chemosensor due to the cavity of calixarene changing from a 'flattened-cone' to a more-upright form and inhibition of PET. In contrast, the results suggested that receptor 1 is highly sensitive and selective for Cu2+ and Fe3+ as a fluorescence quenching type chemosensor due to the photoinduced electron transfer (PET) or heavy atom effect. (C) 2016 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4854 / 4858
页数:5
相关论文
共 51 条
[1]   Tuning of donor-acceptor linker in rhodamine-coumarin conjugates leads remarkable solvent dependent FRET efficiency for Al3+ imaging in HeLa cells [J].
Adhikari, Susanta ;
Mandal, Sandip ;
Ghosh, Avijit ;
Guria, Subhajit ;
Das, Debasis .
SENSORS AND ACTUATORS B-CHEMICAL, 2016, 234 :222-230
[2]  
Atwood JL, 1999, CHEM-EUR J, V5, P990, DOI 10.1002/(SICI)1521-3765(19990301)5:3<990::AID-CHEM990>3.3.CO
[3]  
2-W
[4]   Recent developments in transition metal ion detection by luminescent chemosensors [J].
Bargossi, C ;
Fiorini, MC ;
Montalti, M ;
Prodi, L ;
Zaccheroni, N .
COORDINATION CHEMISTRY REVIEWS, 2000, 208 :17-32
[5]   A SPECTROPHOTOMETRIC INVESTIGATION OF THE INTERACTION OF IODINE WITH AROMATIC HYDROCARBONS [J].
BENESI, HA ;
HILDEBRAND, JH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1949, 71 (08) :2703-2707
[6]   Upper rim appended hybrid calixarenes via click chemistry [J].
Bew, Sean P. ;
Brimage, Rebecca A. ;
L'Hermite, Nathalie ;
Sharma, Sunil V. .
ORGANIC LETTERS, 2007, 9 (19) :3713-3716
[7]   Triazole-modified calix[4]crown as a novel fluorescent on-off switchable chemosensor [J].
Chang, Kai-Chi ;
Su, In-Hao ;
Senthilvelan, Annamalai ;
Chung, Wen-Sheng .
ORGANIC LETTERS, 2007, 9 (17) :3363-3366
[8]  
Connors K. A., 1987, Binding Constants: The Measurement of Molecular Complex Stability
[9]   Biomimetic and self-assembled calix[6]arene-based receptors for neutral molecules [J].
Coquiere, David ;
Le Gac, Stephane ;
Darbost, Ulrich ;
Seneque, Olivier ;
Jabin, Ivan ;
Reinaud, Olivia .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (12) :2485-2500
[10]   Fifty years of oxacalix[3]arenes: A review [J].
Cottet, Kevin ;
Marcos, Paula M. ;
Cragg, Peter J. .
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2012, 8 :201-226