Photocatalytic copper-catalyzed azide-alkyne cycloaddition click reaction with Cu(II) coordination polymer

被引:17
作者
Guo, Xiangyang [1 ]
Zeng, Le [1 ]
Wang, Zhe [1 ]
Zhang, Tiexin [1 ]
He, Cheng [1 ]
Duan, Chunying [1 ]
机构
[1] Dalian Univ Technol, State Key Lab Fine Chem, Dalian 116024, Peoples R China
基金
中国国家自然科学基金;
关键词
METAL-ORGANIC FRAMEWORKS; HETEROGENEOUS CATALYST; HIGHLY EFFICIENT; 1,3-DIPOLAR CYCLOADDITION; DESIGN; CHEMISTRY; OXIDATION; LIGANDS; COMPLEX; WATER;
D O I
10.1039/c7ra10207k
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A two dimensional Cu(II) coordination sheet has been developed. By incorporating well-designed chromophore linkers into the coordination polymer, the long conjugated system caused the maximum UV-vis absorption wavelength red shift to the visible area (up to 550 nm). Adjacent sheets were assembled in an ABAB fashion via pi...pi stacking and C-H...pi interactions to form a three-dimensional structure. The interlayer stacking mode is important because its liability allows for exfoliation of the material which results in the dispersion of the active sites and the enhancement of the visible-light trapping capacity. Using this copper(II) coordination polymer, a series of click reactions were successfully conducted under household light irradiation in the air at room temperature. And 1,4-substituted triazoles were the single products in good yields. Moreover, the catalyst can be easily removed from the reaction mixture.
引用
收藏
页码:52907 / 52913
页数:7
相关论文
共 58 条
[1]   Copper-catalyzed "click" reaction/direct arylation sequence: Modular syntheses of 1,2,3-triazoles [J].
Ackermann, Lutz ;
Potukuchi, Harish K. ;
Landsberg, Dirk ;
Vicente, Ruben .
ORGANIC LETTERS, 2008, 10 (14) :3081-3084
[2]   Spatial and temporal control of the alkyne-azide cycloaddition by photoinitiated Cu(II) reduction [J].
Adzima, Brian J. ;
Tao, Youhua ;
Kloxin, Christopher J. ;
DeForest, Cole A. ;
Anseth, Kristi S. ;
Bowman, Christopher N. .
NATURE CHEMISTRY, 2011, 3 (03) :256-259
[3]   Zeolite-like metal-organic frameworks as platforms for applications:: On metalloporphyrin-based catalysts [J].
Alkordi, Mohamed H. ;
Liu, Yunling ;
Larsen, Randy W. ;
Eubank, Jarrod F. ;
Eddaoudi, Mohamed .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (38) :12639-+
[4]   Constructing star polymers via modular ligation strategies [J].
Altintas, Ozcan ;
Vogt, Andrew P. ;
Barner-Kowollik, Christopher ;
Tunca, Umit .
POLYMER CHEMISTRY, 2012, 3 (01) :34-45
[5]   Synthesis of Terpolymers by Click Reactions [J].
Altintas, Ozcan ;
Tunca, Umit .
CHEMISTRY-AN ASIAN JOURNAL, 2011, 6 (10) :2584-2591
[6]   Star and miktoarm star block (co)polymers via self-assembly of ATRP generated polymer segments featuring Hamilton wedge and cyanuric acid binding motifs [J].
Altintas, Ozcan ;
Tunca, Umit ;
Barner-Kowollik, Christopher .
POLYMER CHEMISTRY, 2011, 2 (05) :1146-1155
[7]   A Highly Efficient Single-Chain Metal Organic Nanoparticle Catalyst for Alkyne-Azide "Click" Reactions in Water and in Cells [J].
Bai, Yugang ;
Feng, Xinxin ;
Xing, Hang ;
Xu, Yanhua ;
Kim, Boo Kyung ;
Baig, Noman ;
Zhou, Tianhui ;
Gewirth, Andrew A. ;
Lu, Yi ;
Oldfield, Eric ;
Zimmerman, Steven C. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (35) :11077-11080
[8]   Terminology of metal-organic frameworks and coordination polymers (IUPAC Recommendations 2013) [J].
Batten, Stuart R. ;
Champness, Neil R. ;
Chen, Xiao-Ming ;
Garcia-Martinez, Javier ;
Kitagawa, Susumu ;
Ohrstrom, Lars ;
O'Keeffe, Michael ;
Suh, Myunghyun Paik ;
Reedijk, Jan .
PURE AND APPLIED CHEMISTRY, 2013, 85 (08) :1715-1724
[9]   Copper-Chelating Azides for Efficient Click Conjugation Reactions in Complex Media [J].
Bevilacqua, Valentina ;
King, Mathias ;
Chaumontet, Manon ;
Nothisen, Marc ;
Gabillet, Sandra ;
Buisson, David ;
Puente, Celine ;
Wagner, Alain ;
Taran, Frederic .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (23) :5872-5876
[10]   Extremely low copper concentrations affect gene expression profiles of human prostate epithelial cell lines [J].
Bigagli, Elisabetta ;
Luceri, Cristina ;
Bernardini, Simonetta ;
Dei, Andrea ;
Dolara, Piero .
CHEMICO-BIOLOGICAL INTERACTIONS, 2010, 188 (01) :214-219