Synthesis and characterization of lead metallated non-peripherally substituted octa-octyl tetrabenzo(aza)porphyrins showing face-to-face columnar stacking in the crystal phase

Sosa-Vargas, Lydia, Coles, Simon J., Tizzard, Graham J., Chambrier, Isabelle, Cook, Michael J. and Cammidge, Andrew N. ORCID: https://orcid.org/0000-0001-7912-4310 (2023) Synthesis and characterization of lead metallated non-peripherally substituted octa-octyl tetrabenzo(aza)porphyrins showing face-to-face columnar stacking in the crystal phase. Journal of Porphyrins and Phthalocyanines, 27 (07n10). pp. 1285-1291. ISSN 1088-4246

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Abstract

The full range of porphyrin-phthalocyanine hybrids can be synthesised by treatment of 1,4-dioctylphthalonitrile with varying equivalents of MeMgBr to produce mixtures favouring specific hybrid structures and the tetrabenzoporphyrin in the extreme case. The individual macrocycles can be isolated in pure form as their magnesium derivatives, and subsequently demetallated to give the parent metal-free compounds. Insertion of lead proceeded smoothly with all hybrids using lead (II) acetate. In the case of monoaza- and triaza-hybrids, the resulting materials could be recrystallised to give crystals suitable for X-ray diffraction. The crystal structures are distinctive from previously reported examples of non-peripherally substituted octaalkyl phthalocyanines and hybrids (metal-free and metallated, including with lead) and they each present infinite stacks of cofacial macrocycles linked through bridging lead ions which, as expected, lie outside of the macrocycle plane.

Item Type: Article
Additional Information: Acknowledgements: The authors thank CONACYT, Mexico, and UEA for funding (LXS-V). MJC gratefully thanks the Leverhulme Foundation for the award of a Leverhulme Emeritus Fellowship. SJC and GJT thank the EPSRC for funding.
Uncontrolled Keywords: lead phthalocyanines,columnar stacks,crystal structure,phthalocyanine-porphyrin hybrids,lead phthalocyanines,chemistry(all) ,/dk/atira/pure/subjectarea/asjc/1600
Faculty \ School: Faculty of Science > School of Chemistry
UEA Research Groups: Faculty of Science > Research Groups > Chemistry of Materials and Catalysis
Faculty of Science > Research Groups > Chemistry of Light and Energy
Faculty of Science > Research Groups > Centre for Photonics and Quantum Science
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Depositing User: LivePure Connector
Date Deposited: 19 Apr 2023 10:30
Last Modified: 18 Jul 2024 02:04
URI: https://ueaeprints.uea.ac.uk/id/eprint/91844
DOI: 10.1142/S1088424623500876

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