Reaction of 4H-cyclopenta[2,1-b:3,4-b′]dithiophenes with NBS - A route toward 2H-cyclopenta[2,1-b:3,4-b′]dithiophene-2,6(4H)-diones

Lidia Marin; Sarah Van Mierloo; Yuexing Zhang; Koen Robeyns; Benoît Champagne; Peter Adriaensens; Laurence Lutsen; Dirk Vanderzande; Wouter Maes

doi:10.1016/j.tet.2013.01.026

Reaction of 4H-cyclopenta[2,1-b:3,4-b′]dithiophenes with NBS - A route toward 2H-cyclopenta[2,1-b:3,4-b′]dithiophene-2,6(4H)-diones

Lidia Marin, Sarah Van Mierloo, Yuexing Zhang, Koen Robeyns, Benoît Champagne, Peter Adriaensens, Laurence Lutsen, Dirk Vanderzande, Wouter Maes^*

^*Corresponding author for this work

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

6 Scopus citations

Abstract

In this paper we present a detailed study of the bromination reaction of cyclopentadithiophene (CPDT) derivatives, by means of NBS, giving access to either 2,6-dibromo-4H-cyclopenta[2,1-b:3,4-b′]dithiophenes or 2H-cyclopenta[2,1-b:3,4-b′]dithiophene-2,6(4H)-diones (CPDT-2,6-diones). The CPDT-2,6-diones are fully characterized, including an X-ray single crystal structure of one of the representative materials. A mechanism leading to the formation of the latter, which arise as a new class of compounds within the CPDT family, is proposed and is supported by Gibbs free energy calculations. The influence of the solvent, reaction time, and the number of equivalents of NBS on the selectivity of the reaction is discussed.

Original language	English (US)
Pages (from-to)	2260-2267
Number of pages	8
Journal	Tetrahedron
Volume	69
Issue number	10
DOIs	https://doi.org/10.1016/j.tet.2013.01.026
State	Published - Mar 11 2013
Externally published	Yes

Keywords

2H-Cyclopenta[2,1-b:3,4-b′]dithiophene-2,6(4H)-dione
4H-Cyclopenta[2,1-b:3,4-b′]dithiophene (CPDT)
Bromination
Gibbs free energy calculations
Solvent effects

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2013.01.026

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title = "Reaction of 4H-cyclopenta[2,1-b:3,4-b′]dithiophenes with NBS - A route toward 2H-cyclopenta[2,1-b:3,4-b′]dithiophene-2,6(4H)-diones",

abstract = "In this paper we present a detailed study of the bromination reaction of cyclopentadithiophene (CPDT) derivatives, by means of NBS, giving access to either 2,6-dibromo-4H-cyclopenta[2,1-b:3,4-b′]dithiophenes or 2H-cyclopenta[2,1-b:3,4-b′]dithiophene-2,6(4H)-diones (CPDT-2,6-diones). The CPDT-2,6-diones are fully characterized, including an X-ray single crystal structure of one of the representative materials. A mechanism leading to the formation of the latter, which arise as a new class of compounds within the CPDT family, is proposed and is supported by Gibbs free energy calculations. The influence of the solvent, reaction time, and the number of equivalents of NBS on the selectivity of the reaction is discussed.",

keywords = "2H-Cyclopenta[2,1-b:3,4-b′]dithiophene-2,6(4H)-dione, 4H-Cyclopenta[2,1-b:3,4-b′]dithiophene (CPDT), Bromination, Gibbs free energy calculations, Solvent effects",

author = "Lidia Marin and {Van Mierloo}, Sarah and Yuexing Zhang and Koen Robeyns and Beno{\^i}t Champagne and Peter Adriaensens and Laurence Lutsen and Dirk Vanderzande and Wouter Maes",

year = "2013",

month = mar,

day = "11",

doi = "10.1016/j.tet.2013.01.026",

language = "English (US)",

volume = "69",

pages = "2260--2267",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier",

number = "10",

}

TY - JOUR

T1 - Reaction of 4H-cyclopenta[2,1-b:3,4-b′]dithiophenes with NBS - A route toward 2H-cyclopenta[2,1-b:3,4-b′]dithiophene-2,6(4H)-diones

AU - Marin, Lidia

AU - Van Mierloo, Sarah

AU - Zhang, Yuexing

AU - Robeyns, Koen

AU - Champagne, Benoît

AU - Adriaensens, Peter

AU - Lutsen, Laurence

AU - Vanderzande, Dirk

AU - Maes, Wouter

PY - 2013/3/11

Y1 - 2013/3/11

N2 - In this paper we present a detailed study of the bromination reaction of cyclopentadithiophene (CPDT) derivatives, by means of NBS, giving access to either 2,6-dibromo-4H-cyclopenta[2,1-b:3,4-b′]dithiophenes or 2H-cyclopenta[2,1-b:3,4-b′]dithiophene-2,6(4H)-diones (CPDT-2,6-diones). The CPDT-2,6-diones are fully characterized, including an X-ray single crystal structure of one of the representative materials. A mechanism leading to the formation of the latter, which arise as a new class of compounds within the CPDT family, is proposed and is supported by Gibbs free energy calculations. The influence of the solvent, reaction time, and the number of equivalents of NBS on the selectivity of the reaction is discussed.

AB - In this paper we present a detailed study of the bromination reaction of cyclopentadithiophene (CPDT) derivatives, by means of NBS, giving access to either 2,6-dibromo-4H-cyclopenta[2,1-b:3,4-b′]dithiophenes or 2H-cyclopenta[2,1-b:3,4-b′]dithiophene-2,6(4H)-diones (CPDT-2,6-diones). The CPDT-2,6-diones are fully characterized, including an X-ray single crystal structure of one of the representative materials. A mechanism leading to the formation of the latter, which arise as a new class of compounds within the CPDT family, is proposed and is supported by Gibbs free energy calculations. The influence of the solvent, reaction time, and the number of equivalents of NBS on the selectivity of the reaction is discussed.

KW - 2H-Cyclopenta[2,1-b:3,4-b′]dithiophene-2,6(4H)-dione

KW - 4H-Cyclopenta[2,1-b:3,4-b′]dithiophene (CPDT)

KW - Bromination

KW - Gibbs free energy calculations

KW - Solvent effects

UR - http://www.scopus.com/inward/record.url?scp=84873414089&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2013.01.026

DO - 10.1016/j.tet.2013.01.026

M3 - Article

AN - SCOPUS:84873414089

SN - 0040-4020

VL - 69

SP - 2260

EP - 2267

JO - Tetrahedron

JF - Tetrahedron

IS - 10

ER -

Reaction of 4H-cyclopenta[2,1-b:3,4-b′]dithiophenes with NBS - A route toward 2H-cyclopenta[2,1-b:3,4-b′]dithiophene-2,6(4H)-diones

Abstract

Keywords

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