The chemiluminescent peroxyoxalate system: state of the art almost 50 years from its discovery

被引:65
作者
Ciscato, Luiz Francisco M. L. [1 ,3 ]
Augusto, Felipe A. [1 ]
Weiss, Dieter [2 ]
Bartoloni, Fernando H. [3 ]
Albrecht, Steffen [4 ]
Brandl, Herbert [5 ]
Zimmermann, Thomas [4 ]
Baader, Wilhelm J. [1 ]
机构
[1] Univ Sao Paulo, Inst Quim, Dept Quim Fundamental, Av Prof Lineu Prestes 748,Sala 1257, BR-05508900 Sao Paulo, Brazil
[2] Univ Jena, Inst Organ Chem & Makromol Chem, D-07743 Jena, Germany
[3] Univ Fed ABC, Ctr Ciencias Nat & Humanas, BR-09210170 Santo Andre, SP, Brazil
[4] Tech Univ Dresden, Klin & Poliklin Frauenheilkunde & Geburtshilfe, D-01307 Dresden, Germany
[5] Gymnasium Kaltenkirchen, D-24568 Kaltenkirchen, Germany
基金
巴西圣保罗研究基金会;
关键词
Peroxyoxalate; chemiluminescence; organic peroxides; excited states; INTRAMOLECULAR ELECTRON-TRANSFER; BIS(2,4-DINITROPHENYL) OXALATE DNPO; HYDROGEN-PEROXIDE; EXCHANGE LUMINESCENCE; CHEMI-LUMINESCENCE; ORGANIC PEROXIDES; CATALYZED CHEMILUMINESCENCE; ENHANCED CHEMILUMINESCENCE; THERMAL-DECOMPOSITION; LIQUID-CHROMATOGRAPHY;
D O I
10.3998/ark.5550190.0013.328
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Almost fifty years after the discovery of the peroxyoxalate reaction by E. A. Chandross in the early nineteen sixties, this review article intends to give a general overview on mechanistic aspects of this system and to describe the principles of its analytical application. After a short general introduction on the principles of chemiluminescence and the history of peroxyoxalate discovery, mechanistic aspects of high-energy intermediate formation, its structure and its reaction with an activator in the peroxyoxalate system are discussed. Finally, analytical applications of peroxyoxalate chemiluminescence are exemplified using representative recent examples, including oxalic acid detection in biological samples.
引用
收藏
页码:391 / 430
页数:40
相关论文
共 144 条
[1]   Viscosity dependence of the chemically induced electron-exchange chemiluminescence triggered from a bicyclic dioxetane [J].
Adam, W ;
Matsumoto, M ;
Trofimov, AV .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (36) :8631-8634
[2]  
ADAM W, 1984, B SOC CHIM BELG, V93, P605
[3]   MECHANISM OF DIRECT AND RUBRENE ENHANCED CHEMILUMINESCENCE DURING ALPHA-PEROXYLACTONE DECARBOXYLATION [J].
ADAM, W ;
SIMPSON, GA ;
YANY, F .
JOURNAL OF PHYSICAL CHEMISTRY, 1974, 78 (25) :2559-2569
[4]   1,2-DIOXETANE - SYNTHESIS, CHARACTERIZATION, STABILITY, AND CHEMI-LUMINESCENCE [J].
ADAM, W ;
BAADER, WJ .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1984, 23 (02) :166-167
[5]   CYCLIC PEROXIDE .81. FLUORESCER-ENHANCED CHEMI-LUMINESCENCE OF ALPHA-PEROXYLACTONES VIA ELECTRON EXCHANGE [J].
ADAM, W ;
CUETO, O .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (22) :6511-6515
[6]   THERMAL GENERATION OF ELECTRONIC EXCITATION WITH HYPERENERGETIC MOLECULES [J].
ADAM, W .
PURE AND APPLIED CHEMISTRY, 1980, 52 (12) :2591-2608
[7]   EFFECTS OF METHYLATION ON THE THERMAL-STABILITY AND CHEMI-LUMINESCENCE PROPERTIES OF 1,2-DIOXETANES [J].
ADAM, W ;
BAADER, WJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (02) :410-416
[8]  
Adam W, 1997, LIEBIGS ANN-RECL, P1359
[9]   Solvent-cage effect (viscosity dependence) as a diagnostic probe for the mechanism of the intramolecular chemically initiated electron-exchange luminescence (CIEEL) triggered from a spiroadamantyl-substituted dioxetane [J].
Adam, W ;
Bronstein, I ;
Trofimov, AV ;
Vasil'ev, RF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (05) :958-961
[10]   From the firefly bioluminescence to the dioxetane-based (AMPPD) chemiluminescence immunoassay: A retroanalysis [J].
Adam, W ;
Reinhardt, D ;
SahaMoller, CR .
ANALYST, 1996, 121 (11) :1527-1531