Photodebromination of dibromobutane

Possibility and evidence

Yun Chiou Lin, Chong Mou Wang

Research output: Contribution to journalArticle

Abstract

The reduction of organic dibromides, such as 2,3-dibromobutane (2,3-DBB), 1,2-dibromobutane (1,2-DBB) and 1,2-dibromocyclohexane, appears to exist with cathodic barrier. For instance, 2,3-DBB can only be reduced at a potential more negative than -1.5 V vs. SCE in DMSO with bare carbon electrodes. To reduce the cathodic overvoltage for 2,3-DBB, we found that cobalt tris(5-aminophenanthroline) (Co (5 -NH2 -phen)32 +) is a useful catalyst. Incorporating Co (5 -NH2 -phen)32 + could shift the onset potential for the reduction of 2,3-DBB to -1 V. As Co (5 -NH2 -phen)32 + was further modified with 1-aminopyrene (1-NH2-Py), the resulting derivative, Py-Co (5 - NH2 -phen)32 +, could shift the onset potential to a more positive value, -0.45 V, as the system was irradiated with white light. Using Py-Co (5 - NH2 -phen)32 + and diethylamine (DEA) as the photocatalyst and sacrificial donor, 2,3-DBB could then be photochemically degraded into butene and bromide ions. IR spectral analysis and bromide-ion analysis confirmed these results. Besides 2,3-DBB, 1,2-DBB and 1,2-dibromocyclohexane could also be degraded under the photosensitization of Py-Co (5 - NH2 -phen)32 +. Accordingly, the proposed photodebromination is considered as an effective alternative for the degradation of organic dibromides, and Py-Co (5 - NH2 -phen)32 + is a potential photocatalyst in this aspect.

Original languageEnglish
Pages (from-to)237-241
Number of pages5
JournalJournal of Electroanalytical Chemistry
Volume601
Issue number1-2
DOIs
Publication statusPublished - 2007 Mar 15

Fingerprint

Photocatalysts
Ions
Butenes
Spectrum analysis
Cobalt
Derivatives
Bromides
Degradation
Electrodes
Catalysts
Carbon
Dimethyl Sulfoxide
2,3-dibromobutane
nitro-bis(2,4-pentanedionato)(pyridine)cobalt(III)

Keywords

  • Cobalt tris(5-aminophenanthroline)
  • Organic dibromide
  • Photodebromination
  • Photosensitization
  • Pyrene

ASJC Scopus subject areas

  • Analytical Chemistry
  • Chemical Engineering(all)
  • Electrochemistry

Cite this

Photodebromination of dibromobutane : Possibility and evidence. / Lin, Yun Chiou; Wang, Chong Mou.

In: Journal of Electroanalytical Chemistry, Vol. 601, No. 1-2, 15.03.2007, p. 237-241.

Research output: Contribution to journalArticle

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abstract = "The reduction of organic dibromides, such as 2,3-dibromobutane (2,3-DBB), 1,2-dibromobutane (1,2-DBB) and 1,2-dibromocyclohexane, appears to exist with cathodic barrier. For instance, 2,3-DBB can only be reduced at a potential more negative than -1.5 V vs. SCE in DMSO with bare carbon electrodes. To reduce the cathodic overvoltage for 2,3-DBB, we found that cobalt tris(5-aminophenanthroline) (Co (5 -NH2 -phen)32 +) is a useful catalyst. Incorporating Co (5 -NH2 -phen)32 + could shift the onset potential for the reduction of 2,3-DBB to -1 V. As Co (5 -NH2 -phen)32 + was further modified with 1-aminopyrene (1-NH2-Py), the resulting derivative, Py-Co (5 - NH2 -phen)32 +, could shift the onset potential to a more positive value, -0.45 V, as the system was irradiated with white light. Using Py-Co (5 - NH2 -phen)32 + and diethylamine (DEA) as the photocatalyst and sacrificial donor, 2,3-DBB could then be photochemically degraded into butene and bromide ions. IR spectral analysis and bromide-ion analysis confirmed these results. Besides 2,3-DBB, 1,2-DBB and 1,2-dibromocyclohexane could also be degraded under the photosensitization of Py-Co (5 - NH2 -phen)32 +. Accordingly, the proposed photodebromination is considered as an effective alternative for the degradation of organic dibromides, and Py-Co (5 - NH2 -phen)32 + is a potential photocatalyst in this aspect.",
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AB - The reduction of organic dibromides, such as 2,3-dibromobutane (2,3-DBB), 1,2-dibromobutane (1,2-DBB) and 1,2-dibromocyclohexane, appears to exist with cathodic barrier. For instance, 2,3-DBB can only be reduced at a potential more negative than -1.5 V vs. SCE in DMSO with bare carbon electrodes. To reduce the cathodic overvoltage for 2,3-DBB, we found that cobalt tris(5-aminophenanthroline) (Co (5 -NH2 -phen)32 +) is a useful catalyst. Incorporating Co (5 -NH2 -phen)32 + could shift the onset potential for the reduction of 2,3-DBB to -1 V. As Co (5 -NH2 -phen)32 + was further modified with 1-aminopyrene (1-NH2-Py), the resulting derivative, Py-Co (5 - NH2 -phen)32 +, could shift the onset potential to a more positive value, -0.45 V, as the system was irradiated with white light. Using Py-Co (5 - NH2 -phen)32 + and diethylamine (DEA) as the photocatalyst and sacrificial donor, 2,3-DBB could then be photochemically degraded into butene and bromide ions. IR spectral analysis and bromide-ion analysis confirmed these results. Besides 2,3-DBB, 1,2-DBB and 1,2-dibromocyclohexane could also be degraded under the photosensitization of Py-Co (5 - NH2 -phen)32 +. Accordingly, the proposed photodebromination is considered as an effective alternative for the degradation of organic dibromides, and Py-Co (5 - NH2 -phen)32 + is a potential photocatalyst in this aspect.

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