Solvent effect on base-induced chemiluminescent decomposition of bicyclic dioxetanes bearing a 3-hydroxyphenyl group

被引：4

作者：

Watanabe, Nobuko ^{[1
]}

Ijuin, Hisako K. ^{[1
]}

Takatsuka, Hikaru ^{[1
]}

Matsumoto, Masakatsu ^{[1
]}

机构：

[1] Kanagawa Univ, Dept Chem, Hiratsuka, Kanagawa 2591293, Japan

来源：

TETRAHEDRON | 2021年 / 88卷

关键词：

Chemiluminescence; Dioxetane; Charge-transfer-induced decomposition; Solvent effect; LSER analysis; ELECTRON-EXCHANGE LUMINESCENCE; SUBSTITUTED DIOXETANES; VISCOSITY DEPENDENCE; APROTIC MEDIUM; CHEMIEXCITATION; PROBES; CIEEL; 1,2-DIOXETANES; FLUORESCENCE; EFFICIENCY;

D O I：

10.1016/j.tet.2021.132147

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chemiluminescent decomposition of dioxetanes bearing a 3-oxidophenyl was investigated in various solvents. The solvent-dependency of chemiluminescence efficiency Phi(CL) showed a hierarchy that could be stratified into three classes: FCL in aprotic polar solvents "in alcohols" in water. Hydrogen bond donor ability of the solvent was mainly responsible to the hierarchy. Singlet-chemiexcitation efficiency was less sensitive to the solvent than fluorescence efficiency of the emitter. (C) 2021 Elsevier Ltd. All rights reserved.

引用

页数：10

共 44 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] Hydrogen-bonding effects on the fluorescence versus electron-transfer-initiated chemiluminescence spectra of the m-oxybenzoate ion derived from a bicyclic dioxetane [J].

Adam, W ;

Matsumoto, M ;

Trofimov, AV .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (07) :2078-2082

[3] Solvatochromic effects on the electron exchange chemiluminescence (CIEEL) of spiroadamantyl-substituted dioxetanes and the fluorescence of relevant oxyanions [J].

Adam, W ;

Bronstein, I ;

Trofimov, AV .

JOURNAL OF PHYSICAL CHEMISTRY A, 1998, 102 (28) :5406-5414

[4] 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

[5] 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

[6] Electron exchange luminescence of spiroadamantane-substituted dioxetanes triggered by alkaline phosphatase. Kinetics and elucidation of pH effects [J].

Adam, W ;

Bronstein, I ;

Edwards, B ;

Engel, T ;

Reinhardt, D ;

Schneider, FW ;

Trofimov, AV ;

Vasilev, RF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (43) :10400-10407

[7]

Adam W., 2006, CHEM PEROXIDES, V2, P1171

[8] Efficiency of Electron Transfer Initiated Chemiluminescence [J].

Augusto, Felipe A. ;

de Souza, Glalci A. ;

de Souza Junior, Sergio P. ;

Khalid, Muhammad ;

Baader, Wilhelm J. .

PHOTOCHEMISTRY AND PHOTOBIOLOGY, 2013, 89 (06) :1299-1317

[9]

Baader W. J., 2006, CHEM PEROXIDES, P1211, DOI DOI 10.1002/0470862769.CH16

[10] APPLICATIONS OF DIOXETANE CHEMILUMINESCENT PROBES TO MOLECULAR-BIOLOGY [J].

BECK, S ;

KOSTER, H .

ANALYTICAL CHEMISTRY, 1990, 62 (21) :2258-2270

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