Aryl substituted adamantane-dipyrromethanes: chromogenic and fluorescent anion sensors

被引：19
作者：
Aleskovic, Marija [1 ]
Basaric, Nikola [1 ]
Halasz, Ivan [2 ]
Liang, Xing [3 ,4 ]
Qin, Wenwu [3 ,4 ]
Mlinaric-Majerski, Kata [1 ]
机构：
[1] Rudjer Boskovic Inst, Dept Organ Chem & Biochem, Zagreb 10000, Croatia
[2] Rudjer Boskovic Inst, Div Mat Chem, Zagreb 10000, Croatia
[3] Lanzhou Univ, Key Lab Nonferrous Met Chem & Resources Utilizat, Lanzhou 730000, Peoples R China
[4] Lanzhou Univ, State Key Lab Appl Organ Chem, Coll Chem & Chem Engn, Lanzhou 730000, Peoples R China
来源：
TETRAHEDRON | 2013年 / 69卷 / 06期
关键词：
Adamantanes; Anion sensors; UV-vis spectrometry; Fluorescence spectrometry; Dipyrromethanes; BINDING; RECEPTORS; RECOGNITION; CARBOXYLATES; LUMINESCENT; DIPEPTIDES; SAPPHYRINS; STATE; WATER; HOST;
D O I：
10.1016/j.tet.2012.12.026
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
New adamantane dipyrromethane anion receptors were synthesized and their photophysical properties and anion binding investigated. In addition, a nitro derivative has been characterized by single crystal X-ray analysis. In the crystal structure, the nitro derivative is complexed with CH3CN molecules, indicating that dipyrromethanes can in principle be employed as neutral molecule hosts. Anion binding ability in CH3CN solutions with TBA salts (F-, Cl-, Br-, AcO-, HSO4-, NO3- and H2PO4-) was investigated by UV-vis, fluorescence and/or H-1 NMR spectroscopy, and the association constants of the corresponding complexes were determined. The receptors form 1:1 complexes with the highest association constants with F- and AcO-. Change of the substituent at the phenyldipyrromethanes results in different photophysical properties, leading to different spectroscopic responses in the presence of anions. Therefore, differently substituted phenyldipyrromethanes can be used as colorimetric or fluorescent anion sensors. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1725 / 1734
页数：10
相关论文
共 77 条
  • [31] Farrugia L.J., 1997, J. Appl. Crystallogr., V30, P565, DOI [10.1107/S0021889897003117, DOI 10.1107/S0021889897003117]
  • [32] Farrugia L. J., 1999, Journal of Applied Crystallography, V32, P837, DOI [DOI 10.1107/S0021889812029111, 10.1107/S0021889899006020, DOI 10.1107/S0021889899006020]
  • [33] Calixpyrroles
    Gale, PA
    Sessler, JL
    Král, V
    [J]. CHEMICAL COMMUNICATIONS, 1998, (01) : 1 - 8
  • [34] Calixpyrroles II
    Gale, PA
    Anzenbacher, P
    Sessler, JL
    [J]. COORDINATION CHEMISTRY REVIEWS, 2001, 222 : 57 - 102
  • [35] Calix[4]pyrroles: Old yet new anion-binding agents
    Gale, PA
    Sessler, JL
    Kral, V
    Lynch, V
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (21) : 5140 - 5141
  • [36] Amidopyrroles: from anion receptors to membrane transport agents
    Gale, PA
    [J]. CHEMICAL COMMUNICATIONS, 2005, (30) : 3761 - 3772
  • [37] 2-amidopyrroles and 2,5-diamidopyrroles as simple anion binding agents
    Gale, PA
    Camiolo, S
    Tizzard, GJ
    Chapman, CP
    Light, ME
    Coles, SJ
    Hursthouse, MB
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (23) : 7849 - 7853
  • [38] Hydrogen-bonding pyrrolic amide cleft anion receptors
    Gale, PA
    Camiolo, S
    Chapman, CP
    Light, ME
    Hursthouse, MB
    [J]. TETRAHEDRON LETTERS, 2001, 42 (30) : 5095 - 5097
  • [39] Anion coordination and anion-templated assembly: Highlights from 2002 to 2004
    Gale, Philip A.
    Quesada, Roberto
    [J]. COORDINATION CHEMISTRY REVIEWS, 2006, 250 (23-24) : 3219 - 3244
  • [40] Anion receptor chemistry: highlights from 2008 and 2009
    Gale, Philip A.
    [J]. CHEMICAL SOCIETY REVIEWS, 2010, 39 (10) : 3746 - 3771
12345678