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

L. Marin; S. Van Mierloo; Y. Zhang; K. Robeyns; B. Champagne; P. Adriaensens; L. Lutsen; D. Vanderzande; W. 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

L. Marin, S. Van Mierloo, Y. Zhang, K. Robeyns, B. Champagne, P. Adriaensens, L. Lutsen, D. Vanderzande, W. Maes

Résultats de recherche: Contribution à un journal/une revue › Article › Revue par des pairs

Résumé

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.

langue originale	Anglais
Pages (de - à)	2260-2267
Nombre de pages	8
journal	Tetrahedron
Volume	69
Numéro de publication	10
Les DOIs	https://doi.org/10.1016/j.tet.2013.01.026
Etat de la publication	Publié - 11 mars 2013

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10.1016/j.tet.2013.01.026

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PAI n°P7/05 - FS2: Systèmes supramoléculaires fonctionnels (PAI P7/05)
CHAMPAGNE, B. (Co-investigateur), De Vos, D. (Responsable du Projet), Van der Auweraer, M. (Co-investigateur), Jérôme, C. (Co-investigateur), Lazzaroni, R. (Co-investigateur), Marin, G. (Co-investigateur), Jonas, A. (Co-investigateur), Du Prez, F. (Co-investigateur), Vanderzande, D. (Co-investigateur), Van Tendeloo, G. (Co-investigateur), Van Speybroeck, V. (Co-investigateur), NENON, S. (Chercheur) & STAELENS, N. (Chercheur)
1/04/12 → 30/09/17
Projet: Recherche
Systèmes supramoléculaires fonctionnels (PAI P6/27)
Champagne, B. (Responsable du Projet), Wouters, J. (Responsable du Projet), BOTEK, E. (Chercheur), DE WERGIFOSSE, M. (Chercheur), GUTHMULLER, J. (Chercheur), Liegeois, V. (Chercheur), NORBERG, B. (Technicien), Plaquet, A. (Chercheur), STAELENS, N. (Chercheur) & Vercauteren, D. (Co-investigateur)
1/01/07 → 31/12/11
Projet: Recherche

Plateforme Technologique Calcul Intensif
Champagne, B. (!!Manager)
Plateforme technologique Calcul intensif
Equipement/installations: Plateforme technolgique

CCDC 912552: Experimental Crystal Structure Determination
Adriaensens, P. (Contributeur), Champagne, B. (Contributeur), Lutsen, L. (Contributeur), Maes, W. (Contributeur), Marin, L. (Contributeur), Robeyns, K. (Contributeur), Van Mierloo, S. (Contributeur), Vanderzande, D. (Contributeur) & Zhang, Y. (Contributeur), Cambridge Crystallographic Data Centre, 1 janv. 2013
DOI: 10.5517/cczml5b, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cczml5b&sid=DataCite
Ensemble de données

Contient cette citation

@article{56e84b7a10be4cb3bfec479dab81edc7,

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.",

author = "L. Marin and {Van Mierloo}, S. and Y. Zhang and K. Robeyns and B. Champagne and P. Adriaensens and L. Lutsen and D. Vanderzande and W. Maes",

year = "2013",

month = mar,

day = "11",

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

language = "English",

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, L.

AU - Van Mierloo, S.

AU - Zhang, Y.

AU - Robeyns, K.

AU - Champagne, B.

AU - Adriaensens, P.

AU - Lutsen, L.

AU - Vanderzande, D.

AU - Maes, W.

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.

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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

Résumé

Accès au document

Autres fichiers et liens

Empreinte digitale

Projets

PAI n°P7/05 - FS2: Systèmes supramoléculaires fonctionnels (PAI P7/05)

Systèmes supramoléculaires fonctionnels (PAI P6/27)

Équipement

Plateforme Technologique Calcul Intensif

Ensembles de données

CCDC 912552: Experimental Crystal Structure Determination

Contient cette citation