Specific Recognition of β-Cyclodextrin by a Tetraphenylethene Luminogen through a Cooperative Boronic Acid/Diol Interaction

被引:32
作者
Liu, Yi [1 ]
Qin, Anjun [1 ]
Chen, Xiujuan [1 ]
Shen, Xiao Yuan [1 ]
Tong, Li [1 ]
Hu, Rongrong [2 ]
Sun, Jing Zhi [1 ]
Tang, Ben Zhong [1 ,2 ]
机构
[1] Zhejiang Univ, Dept Polymer Sci & Engn, MoE Key Lab Macromol Synth & Functionalizat, Hangzhou 310027, Zhejiang, Peoples R China
[2] Hong Kong Univ Sci & Technol, Inst Mol Funct Mat, Dept Chem, Kowloon, Hong Kong, Peoples R China
基金
美国国家科学基金会;
关键词
cooperative effects; cyclodextrins; host-guest systems; molecular recognition; tetraphenylethene; CHIRAL RESOLUTION; SOLID-STATE; COMPLEXATION; RECEPTORS; ACID; CHEMISTRY; EMISSION; BORATE; POLYROTAXANES; DERIVATIVES;
D O I
10.1002/chem.201102613
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An unexpected recognition of β-cyclodextrin (CD) from α- and γ-CDs was achieved. The emission from a diboronic acid-containing tetraphenylethene (TPEDB) was amplified upon addition of β-CD, whereas there was almost no response for α-, and γ-CDs. TPEDB is proposed to be anchored onto the wide rim of β-CD through the alternative and conceptually new cooperative boronic acid/diol dynamic binding interaction, resulting in the restriction of intramolecular rotations of its phenyl rings (see scheme). © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:14736 / 14740
页数:5
相关论文
共 59 条
[1]  
[Anonymous], 2009, ANGEW CHEM, DOI DOI 10.1002/ANGE.200902490
[2]  
[Anonymous], ANGEW CHEM
[3]   Recent advances in the preparation of cyclodextrin-based polyrotaxanes and their applications to soft materials [J].
Araki, Jun ;
Ito, Kohzo .
SOFT MATTER, 2007, 3 (12) :1456-1473
[4]   TOPOGRAPHY OF CYCLODEXTRIN INCLUSION COMPLEXES .20. CIRCULAR AND FLIP-FLOP HYDROGEN-BONDING IN BETA-CYCLODEXTRIN UNDECAHYDRATE - A NEUTRON-DIFFRACTION STUDY [J].
BETZEL, C ;
SAENGER, W ;
HINGERTY, BE ;
BROWN, GM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (24) :7545-7557
[5]   Cyclodextrins as pharmaccutical solubilizers [J].
Brewster, Marcus E. ;
Loftsson, Thorsteinn .
ADVANCED DRUG DELIVERY REVIEWS, 2007, 59 (07) :645-666
[6]   The utility of cyclodextrins for enhancing oral bioavailability [J].
Carrier, Rebecca L. ;
Miller, Lee A. ;
Ahmed, Mran .
JOURNAL OF CONTROLLED RELEASE, 2007, 123 (02) :78-99
[7]   Cyclodextrin-based inclusion complexation bridging supramolecular chemistry and macromolecular self-assembly [J].
Chen, Guosong ;
Jiang, Ming .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (05) :2254-2266
[8]   Synthesis, light emission, nanoaggregation, and restricted intramolecular rotation of 1,1-substituted 2,3,4,5-tetraphenylsiloles [J].
Chen, JW ;
Law, CCW ;
Lam, JWY ;
Dong, YP ;
Lo, SMF ;
Williams, ID ;
Zhu, DB ;
Tang, BZ .
CHEMISTRY OF MATERIALS, 2003, 15 (07) :1535-1546
[9]   Cyclodextrin-based bioactive supramolecular assemblies [J].
Chen, Yong ;
Liu, Yu .
CHEMICAL SOCIETY REVIEWS, 2010, 39 (02) :495-505
[10]   Dynamic combinatorial chemistry [J].
Corbett, Peter T. ;
Leclaire, Julien ;
Vial, Laurent ;
West, Kevin R. ;
Wietor, Jean-Luc ;
Sanders, Jeremy K. M. ;
Otto, Sijbren .
CHEMICAL REVIEWS, 2006, 106 (09) :3652-3711