Electrogenerated chemiluminescence of sterically hindered porphyrins in aqueous media

Fang-Chung Chen; J. H. Ho; C. Y. Chen; Y. O. Su; T. I. Ho

doi:10.1016/S0022-0728(00)00439-3

Electrogenerated chemiluminescence of sterically hindered porphyrins in aqueous media

Fang-Chung Chen, J. H. Ho, C. Y. Chen, Y. O. Su^*, T. I. Ho

^*Corresponding author for this work

Department of Photonics

Research output: Contribution to journal › Article › peer-review

26 Scopus citations

Abstract

A sterically hindered water-soluble porphyrin, tetrakis(3-sulfonatomesityl)porphyrin (H₂TSMP), could form stable radical cation in aqueous media after electrochemical one electron oxidation. The anodic oxidation of H₂TSMP in the presence of tripropylamine or C₂O₄^2- as a coreactant in aqueous solution produces electrogenerated chemiluminescence (ECL) with maxima at 640 and 700 nm. The same emission spectrum of ECL and fluorescence indicates that the ECL emission is from the singlet state of H₂TSMP. The annihilation reactions of ZnTSMP^·+ and ZnTSMP^·-, which are generated electrochemically, in CH₃CN + H₂O (1:1) mixed solution results in an emission which is identical to the photoluminescence. Protection of the active sites against the nucleophilic attack of water or OH^- by sterical hinderance is a successful strategy in designing new ECL-active compounds in aqueous media. Both ECL reaction mechanisms are proposed.

Original language	English
Pages (from-to)	17-23
Number of pages	7
Journal	Journal of Electroanalytical Chemistry
Volume	499
Issue number	1
DOIs	https://doi.org/10.1016/S0022-0728(00)00439-3
State	Published - 23 Feb 2001

Keywords

Electrogenerated chemiluminescence
Porphyrins
Sterically hindered

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title = "Electrogenerated chemiluminescence of sterically hindered porphyrins in aqueous media",

abstract = "A sterically hindered water-soluble porphyrin, tetrakis(3-sulfonatomesityl)porphyrin (H2TSMP), could form stable radical cation in aqueous media after electrochemical one electron oxidation. The anodic oxidation of H2TSMP in the presence of tripropylamine or C2O42- as a coreactant in aqueous solution produces electrogenerated chemiluminescence (ECL) with maxima at 640 and 700 nm. The same emission spectrum of ECL and fluorescence indicates that the ECL emission is from the singlet state of H2TSMP. The annihilation reactions of ZnTSMP·+ and ZnTSMP·-, which are generated electrochemically, in CH3CN + H2O (1:1) mixed solution results in an emission which is identical to the photoluminescence. Protection of the active sites against the nucleophilic attack of water or OH- by sterical hinderance is a successful strategy in designing new ECL-active compounds in aqueous media. Both ECL reaction mechanisms are proposed.",

keywords = "Electrogenerated chemiluminescence, Porphyrins, Sterically hindered",

author = "Fang-Chung Chen and Ho, {J. H.} and Chen, {C. Y.} and Su, {Y. O.} and Ho, {T. I.}",

year = "2001",

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doi = "10.1016/S0022-0728(00)00439-3",

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T1 - Electrogenerated chemiluminescence of sterically hindered porphyrins in aqueous media

AU - Chen, Fang-Chung

AU - Ho, J. H.

AU - Chen, C. Y.

AU - Su, Y. O.

AU - Ho, T. I.

PY - 2001/2/23

Y1 - 2001/2/23

N2 - A sterically hindered water-soluble porphyrin, tetrakis(3-sulfonatomesityl)porphyrin (H2TSMP), could form stable radical cation in aqueous media after electrochemical one electron oxidation. The anodic oxidation of H2TSMP in the presence of tripropylamine or C2O42- as a coreactant in aqueous solution produces electrogenerated chemiluminescence (ECL) with maxima at 640 and 700 nm. The same emission spectrum of ECL and fluorescence indicates that the ECL emission is from the singlet state of H2TSMP. The annihilation reactions of ZnTSMP·+ and ZnTSMP·-, which are generated electrochemically, in CH3CN + H2O (1:1) mixed solution results in an emission which is identical to the photoluminescence. Protection of the active sites against the nucleophilic attack of water or OH- by sterical hinderance is a successful strategy in designing new ECL-active compounds in aqueous media. Both ECL reaction mechanisms are proposed.

AB - A sterically hindered water-soluble porphyrin, tetrakis(3-sulfonatomesityl)porphyrin (H2TSMP), could form stable radical cation in aqueous media after electrochemical one electron oxidation. The anodic oxidation of H2TSMP in the presence of tripropylamine or C2O42- as a coreactant in aqueous solution produces electrogenerated chemiluminescence (ECL) with maxima at 640 and 700 nm. The same emission spectrum of ECL and fluorescence indicates that the ECL emission is from the singlet state of H2TSMP. The annihilation reactions of ZnTSMP·+ and ZnTSMP·-, which are generated electrochemically, in CH3CN + H2O (1:1) mixed solution results in an emission which is identical to the photoluminescence. Protection of the active sites against the nucleophilic attack of water or OH- by sterical hinderance is a successful strategy in designing new ECL-active compounds in aqueous media. Both ECL reaction mechanisms are proposed.

KW - Electrogenerated chemiluminescence

KW - Porphyrins

KW - Sterically hindered

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U2 - 10.1016/S0022-0728(00)00439-3

DO - 10.1016/S0022-0728(00)00439-3

M3 - Article

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EP - 23

JO - Journal of Electroanalytical Chemistry

JF - Journal of Electroanalytical Chemistry

SN - 0368-1874

IS - 1

ER -

Electrogenerated chemiluminescence of sterically hindered porphyrins in aqueous media

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Keywords

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