Detection of Biologically Important Anions in Aqueous Media by Dicationic Azaborines Bearing Ammonio or Phosphonio Groups

被引:98
作者
Agou, Tomohiro [1 ]
Sekine, Masaki [1 ]
Kobayashi, Junji [1 ]
Kawashima, Takayuki [1 ]
机构
[1] Univ Tokyo, Dept Chem, Grad Sch Sci, Bunkyo Ku, Tokyo 1130033, Japan
关键词
analytical methods; azaborines; cyanides; fluorides; main group elements; sensors; PI-ELECTRON SYSTEMS; FLUORIDE-ION; OPTICAL-PROPERTIES; CHARGE-TRANSFER; LEWIS ACIDITY; CYANIDE; FLUORESCENT; COMPLEXATION; RECOGNITION; SENSORS;
D O I
10.1002/chem.200802159
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
New cationic triarylboranes bearing ammonio or phosphonio groups on the periphery were synthesized from a common intermediate, a dibromodibenzoazaborine. These cationic molecules are soluble in highly polar organic solvents as well as water, and they exhibit strong light absorption and photoluminescence emission in water. Complexation of the cationic azaborines with fluoride and cyanide ions in aqueous media proceeded and could be monitored by NMR, UV/Vis, and fluorescence spectroscopy.
引用
收藏
页码:5056 / 5062
页数:7
相关论文
共 52 条
[41]   Pyrrolic and polypyrrolic anion binding agents [J].
Sessler, JL ;
Camiolo, S ;
Gale, PA .
COORDINATION CHEMISTRY REVIEWS, 2003, 240 (1-2) :17-55
[42]   The benzil rearrangement reaction: Trapping of a hitherto minor product and its application to the development of a selective cyanide anion indicator [J].
Sessler, Jonathan L. ;
Cho, Dong-Gyu .
ORGANIC LETTERS, 2008, 10 (01) :73-75
[43]   A modular approach to anion binding podands: adaptability in design and synthesis leads to adaptability in properties [J].
Steed, Jonathan W. .
CHEMICAL COMMUNICATIONS, 2006, (25) :2637-2649
[44]   Chemical sensors based on amplifying fluorescent conjugated polymers [J].
Thomas, Samuel W., III ;
Joly, Guy D. ;
Swager, Timothy M. .
CHEMICAL REVIEWS, 2007, 107 (04) :1339-1386
[45]   Chromogenic oxazines for cyanide detection [J].
Tomasulo, M ;
Sortino, S ;
White, AJP ;
Raymo, FM .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (02) :744-753
[46]   Selective turn-on fluorescence detection of cyanide in water using hydrophobic CdSe quantum dots [J].
Touceda-Varela, Angeles ;
Stevenson, Emily I. ;
Galve-Gasion, Jose A. ;
Dryden, David T. F. ;
Mareque-Rivas, Juan C. .
CHEMICAL COMMUNICATIONS, 2008, (17) :1998-2000
[47]  
*WHO INT PROGR CHE, 2002, ENV HLTH CRIT
[48]   An ammonia equivalent for the palladium-catalyzed amination of aryl halides and triflates [J].
Wolfe, JP ;
Ahman, J ;
Sadighi, JP ;
Singer, RA ;
Buchwald, SL .
TETRAHEDRON LETTERS, 1997, 38 (36) :6367-6370
[49]   Tri-9-anthrylborane and its derivatives:: New boron-containing π-electron systems with divergently extended π-conjugation through boron [J].
Yamaguchi, S ;
Akiyama, S ;
Tamao, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (26) :6335-6336
[50]   Colorimetric fluoride ion sensing by boron-containing π-electron systems [J].
Yamaguchi, S ;
Akiyama, S ;
Tamao, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (46) :11372-11375