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Synthesis and characterization of some octaalkyl substituted lead phthalocyanines and unexpected variations in lead lability arising from the position of substituents and their chain length

Synthesis and characterization of some octaalkyl substituted lead phthalocyanines and unexpected variations in lead lability arising from the position of substituents and their chain length
Synthesis and characterization of some octaalkyl substituted lead phthalocyanines and unexpected variations in lead lability arising from the position of substituents and their chain length
The preparation of some peripherally substituted (2,3,9,10,16,17,23,24) and non-peripherally substituted (1,4,8,11,15,18,22,25) octaalkyl lead(II) phthalocyanines with different alkyl chain lengths (6, 7, 8 or 9 carbons) is described and a comparison of some of their properties reported. X-ray structure analyses of the isomeric peripheral and non-peripheral octakis(octyl)phthalocyaninato lead(II) compounds reveal a greater degree of distortion of the ligand ring system from planarity in the former derivative. The series of peripherally substituted octaalkyl lead(II) phthalocyanines exhibit columnar liquid crystal behavior whereas the non-peripherally substituted isomers do not. The lability of the lead ion was investigated using H-1 NMR spectrometry under a specific set of conditions (8.8 x 10(-4) M solutions of the phthalocyanine in d(8)-toluene containing d(4)-acetic acid 2.06 x 10(-5) M). All the compounds underwent acid catalyzed demetalation at rates dependent upon the location of the substituents and, more surprisingly, the chain length of the alkyl groups. Under these conditions the lead ion within each of the peripherally substituted octaalkyl lead phthalocyanines was more labile than that in the non-peripherally substituted isomer.
1088-4246
511-521
Sosa-Vargas, Lydia X.
4181d890-a74f-4324-a24f-bdc478ec2a9c
Chambrier, Isabelle
d3ad81b8-12d1-4f7a-bc04-99da7f4c0d50
MacDonald, Colin J.
98fac77b-11ef-4981-a908-572a7f03f57e
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Tizzard, Graham J.
8474c0fa-40df-43a6-a662-7f3c4722dbf2
Cammidge, Andrew N.
e7a6b5be-5613-416e-8f1a-40b4744ecf65
Cook, Michael J.
9b30e5b0-b828-46a7-a1f6-cd758c3c6c74
Sosa-Vargas, Lydia X.
4181d890-a74f-4324-a24f-bdc478ec2a9c
Chambrier, Isabelle
d3ad81b8-12d1-4f7a-bc04-99da7f4c0d50
MacDonald, Colin J.
98fac77b-11ef-4981-a908-572a7f03f57e
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Tizzard, Graham J.
8474c0fa-40df-43a6-a662-7f3c4722dbf2
Cammidge, Andrew N.
e7a6b5be-5613-416e-8f1a-40b4744ecf65
Cook, Michael J.
9b30e5b0-b828-46a7-a1f6-cd758c3c6c74

Sosa-Vargas, Lydia X., Chambrier, Isabelle, MacDonald, Colin J., Coles, Simon J., Tizzard, Graham J., Cammidge, Andrew N. and Cook, Michael J. (2013) Synthesis and characterization of some octaalkyl substituted lead phthalocyanines and unexpected variations in lead lability arising from the position of substituents and their chain length. Journal of Porphyrins and Phthalocyanines, 17 (06n07), 511-521. (doi:10.1142/S108842461350020X).

Record type: Article

Abstract

The preparation of some peripherally substituted (2,3,9,10,16,17,23,24) and non-peripherally substituted (1,4,8,11,15,18,22,25) octaalkyl lead(II) phthalocyanines with different alkyl chain lengths (6, 7, 8 or 9 carbons) is described and a comparison of some of their properties reported. X-ray structure analyses of the isomeric peripheral and non-peripheral octakis(octyl)phthalocyaninato lead(II) compounds reveal a greater degree of distortion of the ligand ring system from planarity in the former derivative. The series of peripherally substituted octaalkyl lead(II) phthalocyanines exhibit columnar liquid crystal behavior whereas the non-peripherally substituted isomers do not. The lability of the lead ion was investigated using H-1 NMR spectrometry under a specific set of conditions (8.8 x 10(-4) M solutions of the phthalocyanine in d(8)-toluene containing d(4)-acetic acid 2.06 x 10(-5) M). All the compounds underwent acid catalyzed demetalation at rates dependent upon the location of the substituents and, more surprisingly, the chain length of the alkyl groups. Under these conditions the lead ion within each of the peripherally substituted octaalkyl lead phthalocyanines was more labile than that in the non-peripherally substituted isomer.

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Published date: June 2013
Organisations: Organic Chemistry: Synthesis, Catalysis and Flow, Chemistry, Faculty of Natural and Environmental Sciences

Identifiers

Local EPrints ID: 362494
URI: http://eprints.soton.ac.uk/id/eprint/362494
ISSN: 1088-4246
PURE UUID: d608f142-9b87-44de-a0a1-d695a380eb7c
ORCID for Simon J. Coles: ORCID iD orcid.org/0000-0001-8414-9272
ORCID for Graham J. Tizzard: ORCID iD orcid.org/0000-0002-1577-5779

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Date deposited: 25 Feb 2014 14:30
Last modified: 18 Feb 2021 16:57

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Contributors

Author: Lydia X. Sosa-Vargas
Author: Isabelle Chambrier
Author: Colin J. MacDonald
Author: Simon J. Coles ORCID iD
Author: Andrew N. Cammidge
Author: Michael J. Cook

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