Supramolecular polymers of 4,5-bis(bromomethyl)-1,3-dithiole-2-thione-dihalogen adducts

Louise Lee, David J. Crouch, Shaun P. Wright, Rory Berridge, Peter J. Skabara, Neil Bricklebank, Simon J. Coles, Mark E. Light, Michael B. Hursthouse

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

The title compound has been reacted with I-2, IBr and ICl to afford the charge-transfer adducts 4.2I(2), 4.IBr and 4.ICl.I-2, respectively. The products have been characterised by Raman and IR spectroscopy and X-ray crystallography. The adducts contain linear S...I-X (X=I, Br or Cl) units (174-178degrees) in which the S...I contacts range from 2.534-2.597 AAngstrom. In 4.2I(2) and 4.ICl.I-2, the materials contain additional 'free' diiodine units which are held within a matrix of intermolecular contacts, predominantly through non-covalent halogen halogen and sulfur-halogen interactions. Although the functional groups in the parent molecule (4) are inert at the supramolecular level, the bromomethyl groups in the adducts contribute strong interactions through Br...Br, Br...I, Br...S and Br...H close contacts. The structures of the complexes are polymeric in nature, providing interactions in two and three dimensions.
LanguageEnglish
Pages612-617
Number of pages5
JournalCrystEngComm
Volume6
DOIs
Publication statusPublished - 24 Nov 2004

Fingerprint

Thiones
Halogens
X ray crystallography
halogens
Functional groups
adducts
Raman spectroscopy
Charge transfer
Infrared spectroscopy
Polymers
Sulfur
Molecules
polymers
crystallography
sulfur
charge transfer
interactions
products
matrices
spectroscopy

Keywords

  • halogen-halogen interactions
  • iodine monobromide
  • crystal
  • dihalogens
  • moleculaes
  • sulfur
  • bromo

Cite this

Lee, L., Crouch, D. J., Wright, S. P., Berridge, R., Skabara, P. J., Bricklebank, N., ... Hursthouse, M. B. (2004). Supramolecular polymers of 4,5-bis(bromomethyl)-1,3-dithiole-2-thione-dihalogen adducts. CrystEngComm, 6, 612-617. https://doi.org/10.1039/b416813p
Lee, Louise ; Crouch, David J. ; Wright, Shaun P. ; Berridge, Rory ; Skabara, Peter J. ; Bricklebank, Neil ; Coles, Simon J. ; Light, Mark E. ; Hursthouse, Michael B. / Supramolecular polymers of 4,5-bis(bromomethyl)-1,3-dithiole-2-thione-dihalogen adducts. In: CrystEngComm. 2004 ; Vol. 6. pp. 612-617.
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abstract = "The title compound has been reacted with I-2, IBr and ICl to afford the charge-transfer adducts 4.2I(2), 4.IBr and 4.ICl.I-2, respectively. The products have been characterised by Raman and IR spectroscopy and X-ray crystallography. The adducts contain linear S...I-X (X=I, Br or Cl) units (174-178degrees) in which the S...I contacts range from 2.534-2.597 AAngstrom. In 4.2I(2) and 4.ICl.I-2, the materials contain additional 'free' diiodine units which are held within a matrix of intermolecular contacts, predominantly through non-covalent halogen halogen and sulfur-halogen interactions. Although the functional groups in the parent molecule (4) are inert at the supramolecular level, the bromomethyl groups in the adducts contribute strong interactions through Br...Br, Br...I, Br...S and Br...H close contacts. The structures of the complexes are polymeric in nature, providing interactions in two and three dimensions.",
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Lee, L, Crouch, DJ, Wright, SP, Berridge, R, Skabara, PJ, Bricklebank, N, Coles, SJ, Light, ME & Hursthouse, MB 2004, 'Supramolecular polymers of 4,5-bis(bromomethyl)-1,3-dithiole-2-thione-dihalogen adducts' CrystEngComm, vol. 6, pp. 612-617. https://doi.org/10.1039/b416813p

Supramolecular polymers of 4,5-bis(bromomethyl)-1,3-dithiole-2-thione-dihalogen adducts. / Lee, Louise; Crouch, David J.; Wright, Shaun P.; Berridge, Rory; Skabara, Peter J.; Bricklebank, Neil; Coles, Simon J.; Light, Mark E.; Hursthouse, Michael B.

In: CrystEngComm, Vol. 6, 24.11.2004, p. 612-617.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Supramolecular polymers of 4,5-bis(bromomethyl)-1,3-dithiole-2-thione-dihalogen adducts

AU - Lee, Louise

AU - Crouch, David J.

AU - Wright, Shaun P.

AU - Berridge, Rory

AU - Skabara, Peter J.

AU - Bricklebank, Neil

AU - Coles, Simon J.

AU - Light, Mark E.

AU - Hursthouse, Michael B.

PY - 2004/11/24

Y1 - 2004/11/24

N2 - The title compound has been reacted with I-2, IBr and ICl to afford the charge-transfer adducts 4.2I(2), 4.IBr and 4.ICl.I-2, respectively. The products have been characterised by Raman and IR spectroscopy and X-ray crystallography. The adducts contain linear S...I-X (X=I, Br or Cl) units (174-178degrees) in which the S...I contacts range from 2.534-2.597 AAngstrom. In 4.2I(2) and 4.ICl.I-2, the materials contain additional 'free' diiodine units which are held within a matrix of intermolecular contacts, predominantly through non-covalent halogen halogen and sulfur-halogen interactions. Although the functional groups in the parent molecule (4) are inert at the supramolecular level, the bromomethyl groups in the adducts contribute strong interactions through Br...Br, Br...I, Br...S and Br...H close contacts. The structures of the complexes are polymeric in nature, providing interactions in two and three dimensions.

AB - The title compound has been reacted with I-2, IBr and ICl to afford the charge-transfer adducts 4.2I(2), 4.IBr and 4.ICl.I-2, respectively. The products have been characterised by Raman and IR spectroscopy and X-ray crystallography. The adducts contain linear S...I-X (X=I, Br or Cl) units (174-178degrees) in which the S...I contacts range from 2.534-2.597 AAngstrom. In 4.2I(2) and 4.ICl.I-2, the materials contain additional 'free' diiodine units which are held within a matrix of intermolecular contacts, predominantly through non-covalent halogen halogen and sulfur-halogen interactions. Although the functional groups in the parent molecule (4) are inert at the supramolecular level, the bromomethyl groups in the adducts contribute strong interactions through Br...Br, Br...I, Br...S and Br...H close contacts. The structures of the complexes are polymeric in nature, providing interactions in two and three dimensions.

KW - halogen-halogen interactions

KW - iodine monobromide

KW - crystal

KW - dihalogens

KW - moleculaes

KW - sulfur

KW - bromo

UR - http://www.rsc.org/ej/CE/2004/b416813p.pdf

UR - http://dx.doi.org/10.1039/b416813p

U2 - 10.1039/b416813p

DO - 10.1039/b416813p

M3 - Article

VL - 6

SP - 612

EP - 617

JO - CrystEngComm

T2 - CrystEngComm

JF - CrystEngComm

SN - 1466-8033

ER -

Lee L, Crouch DJ, Wright SP, Berridge R, Skabara PJ, Bricklebank N et al. Supramolecular polymers of 4,5-bis(bromomethyl)-1,3-dithiole-2-thione-dihalogen adducts. CrystEngComm. 2004 Nov 24;6:612-617. https://doi.org/10.1039/b416813p