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CT-adduct vs. pyridinium polyhalide salt formation in the reactions between polypyridyl donors and dihalogens: reactivity of 1,4-di-(3?-pyridylethynyl)benzene towards Br2 and I2

CT-adduct vs. pyridinium polyhalide salt formation in the reactions between polypyridyl donors and dihalogens: reactivity of 1,4-di-(3?-pyridylethynyl)benzene towards Br2 and I2
CT-adduct vs. pyridinium polyhalide salt formation in the reactions between polypyridyl donors and dihalogens: reactivity of 1,4-di-(3?-pyridylethynyl)benzene towards Br2 and I2
The reactions of 1,4-di-(3'-pyridylethynyl) benzene (L) with I-2 and Br-2 in CH2Cl2 afforded 1 and 2, respectively: the former compound features CT-adduct units L center dot 2I(2) connected by a third diiodine molecule to give (L center dot I-6)infinity chains, while the latter is a salt where the monocation HL'+, derived from the N-protonation of a pyridine unit and dibromination of the triple C-C bonds of L, is counterbalanced by an asymmetric tribromide. The isolation of 1 and 2 provides a striking example of how the competition between the Lewis and Bronsted-Lowry basicity of polypyridyl donors can be exploited for the rational design of either neutral or charged building blocks of supramolecular architectures.
1466-8033
6319-6322
Aragoni, M. Carla
3e73ed7a-2cf7-4f5e-9359-61d6e34a6cd5
Arca, Massimiliano
f90b59f6-4dfb-471d-912e-3515e6507165
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Devillanova, Francesco A.
a1015716-6d8a-4517-aac8-593b78e91561
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Coles, Susanne L.
b12334cf-6058-4a34-b409-81076d6c096f
Isaia, Francesco
11f997fe-81a3-4298-bbdc-15e5f2bf18cc
Lippolis, Vito
d9833a14-4aab-4827-a2ba-be818871dcf5
Mancini, Annalisa
da134433-ee68-449c-9d2f-cad90b37a553
Aragoni, M. Carla
3e73ed7a-2cf7-4f5e-9359-61d6e34a6cd5
Arca, Massimiliano
f90b59f6-4dfb-471d-912e-3515e6507165
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Devillanova, Francesco A.
a1015716-6d8a-4517-aac8-593b78e91561
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Coles, Susanne L.
b12334cf-6058-4a34-b409-81076d6c096f
Isaia, Francesco
11f997fe-81a3-4298-bbdc-15e5f2bf18cc
Lippolis, Vito
d9833a14-4aab-4827-a2ba-be818871dcf5
Mancini, Annalisa
da134433-ee68-449c-9d2f-cad90b37a553

Aragoni, M. Carla, Arca, Massimiliano, Coles, Simon J., Devillanova, Francesco A., Hursthouse, Michael B., Coles, Susanne L., Isaia, Francesco, Lippolis, Vito and Mancini, Annalisa (2011) CT-adduct vs. pyridinium polyhalide salt formation in the reactions between polypyridyl donors and dihalogens: reactivity of 1,4-di-(3?-pyridylethynyl)benzene towards Br2 and I2. CrystEngComm, 13 (21), 6319-6322. (doi:10.1039/c1ce05954h).

Record type: Article

Abstract

The reactions of 1,4-di-(3'-pyridylethynyl) benzene (L) with I-2 and Br-2 in CH2Cl2 afforded 1 and 2, respectively: the former compound features CT-adduct units L center dot 2I(2) connected by a third diiodine molecule to give (L center dot I-6)infinity chains, while the latter is a salt where the monocation HL'+, derived from the N-protonation of a pyridine unit and dibromination of the triple C-C bonds of L, is counterbalanced by an asymmetric tribromide. The isolation of 1 and 2 provides a striking example of how the competition between the Lewis and Bronsted-Lowry basicity of polypyridyl donors can be exploited for the rational design of either neutral or charged building blocks of supramolecular architectures.

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Published date: September 2011
Organisations: Chemistry

Identifiers

Local EPrints ID: 347413
URI: https://eprints.soton.ac.uk/id/eprint/347413
ISSN: 1466-8033
PURE UUID: 86010723-b3dd-42bd-bc31-8c057c346583
ORCID for Simon J. Coles: ORCID iD orcid.org/0000-0001-8414-9272

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Date deposited: 04 Feb 2013 15:54
Last modified: 20 Jul 2019 01:09

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Contributors

Author: M. Carla Aragoni
Author: Massimiliano Arca
Author: Simon J. Coles ORCID iD
Author: Francesco A. Devillanova
Author: Susanne L. Coles
Author: Francesco Isaia
Author: Vito Lippolis
Author: Annalisa Mancini

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