Optical and electrochemical properties of heteroditopic ion receptors derived from crown ether-based calix[4]arene with amido-anthraquinone pendants

被引:24
作者
Chailap, Benjamat [1 ]
Tuntulani, Thawatchai [1 ]
机构
[1] Chulalongkorn Univ, Fac Sci, Dept Chem, Bangkok 10330, Thailand
关键词
COLORIMETRIC SENSOR; ANION; RECOGNITION; FLUORIDE; CHEMOSENSOR; CATION; METAL; UREA; COMPLEXATION; HIGHLIGHTS;
D O I
10.1039/c2ob00048b
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Two heteroditopic receptors based on a calix[4]arene crown ether containing amidoanthraquinone pendants in cone and 1,3-alternate conformations (1 and 2, respectively) were synthesized. Photophysical properties of 1 and 2 were studied by UV-vis and fluorescence spectrophotometry in dried CH3CN. Both 1 and 2 showed the highest sensitivity towards F- through the appearance of a new charge transfer band at 500 nm and the enhancement of the emission spectra at lambda(cm) = 542 nm and 528 nm respectively. Interestingly, in the presence of K+, the fluorescence intensity of 1 at 542 nm increased around 2 fold compared to that in the absence of K+ upon addition of F-, while this phenomenon was not observed in the case of receptor 2. Cyclic voltammograms of receptors 1 and 2 showed two consecutive one-electron reversible waves in 40% v/v CH3CN in CH2Cl2, corresponding to two single-electron reductions to give mono- and dianions species at E1/2I = -1.21 V and E1/2II = -1.66 V as well as E1/2I = -1.25 V and E1/2II = -1.71 V, respectively. H2PO4- gave remarkable potential shifts (ca. 200 mV) of the second reduction waves (E1/2II) of both free 1 and 2. In the presence of K+, only receptor 1 gave remarkable potential shifts in its redox wave II upon adding F- and AcO-. Therefore, receptors 1 and 2 exhibited dual sensing modes by fluorescence spectrophotometry and cyclic voltammetry. The topology of ligands also played an important role in cooperative binding properties of heteroditopic receptor 1 possessing a closer distance between a cation and an anion binding. On the other hand, the two ion binding sites of receptor 2 were separated by a longer distance and did not support the cooperative binding. This resulted in the abstraction of K+ from receptor 2 upon addition of anions.
引用
收藏
页码:3617 / 3625
页数:9
相关论文
共 48 条
[1]   A Simple but Effective Dual Redox and Fluorescent Ion Pair Receptor Based on a Ferrocene-Imidazopyrene Dyad [J].
Alfonso, Maria ;
Espinosa, Arturo ;
Tarraga, Alberto ;
Molina, Pedro .
ORGANIC LETTERS, 2011, 13 (08) :2078-2081
[2]   Ferrocene-Based Heteroditopic Receptors Displaying High Selectivity toward Lead and Mercury Metal Cations through Different Channels [J].
Alfonso, Maria ;
Tarraga, Alberto ;
Molina, Pedro .
JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (03) :939-947
[3]   Synthesis and ion sensing properties of new colorimetric and fluorimetric chemosensors based on bithienyl-imidazo-anthraquinone chromophores [J].
Batista, Rosa M. F. ;
Oliveira, Elisabete ;
Costa, Susana P. G. ;
Lodeiro, Carlos ;
Raposo, M. Manuela M. .
ORGANIC LETTERS, 2007, 9 (17) :3201-3204
[4]   Transition metal and organometallic anion complexation agents [J].
Beer, PD ;
Hayes, EJ .
COORDINATION CHEMISTRY REVIEWS, 2003, 240 (1-2) :167-189
[5]  
Beer PD, 2001, ANGEW CHEM INT EDIT, V40, P486, DOI 10.1002/1521-3773(20010202)40:3<486::AID-ANIE486>3.0.CO
[6]  
2-P
[7]   Electrochemical measurement of switchable hydrogen bonding in an anthraquinone-based anion receptor [J].
Brooks, SJ ;
Birkin, PR ;
Gale, PA .
ELECTROCHEMISTRY COMMUNICATIONS, 2005, 7 (12) :1351-1356
[8]   A PCT-based, pyrene-armed calix[4]crown fluoroionophore [J].
Choi, Jung Kyu ;
Kim, Su Ho ;
Yoon, Juyoung ;
Lee, Keun-Hyeung ;
Bartsch, Richard A. ;
Kim, Jong Seung .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (21) :8011-8015
[9]   Anion and ion-pair receptor chemistry: highlights from 2000 and 2001 [J].
Gale, PA .
COORDINATION CHEMISTRY REVIEWS, 2003, 240 (1-2) :191-221
[10]   Anion receptors based on organic frameworks:: highlights from 2005 and 2006 [J].
Gale, Philip A. ;
Garcia-Garrido, Sergio E. ;
Garric, Joachim .
CHEMICAL SOCIETY REVIEWS, 2008, 37 (01) :151-190