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ToolsChambrier, Isabelle, Fotev, Valentin, Hughes, David L. and Cammidge, Andrew N. (2025) Design and synthesis of a sterically locked, highly distorted phthalocyanine and observation of all possible stereoisomers. Journal of Porphyrins and Phthalocyanines, 29 (03n04). pp. 528-533. ISSN 1088-4246
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Abstract
Disruption of the planarity of porphyrinoid cores significantly impacts both spectroscopic and solubility properties and is a useful tool in molecular design. Here, we present the synthesis of a highly distorted phthalocyanine from a rigid, laterally extended phthalonitrile in which the extension is directed toward the core. This arrangement challenges macrocycle formation and aromatisation, such that forcing conditions and zinc templating are required. The phthalocyanine formed is a mixture of 4 isomers (2 of which are chiral, so there are 6 stereoisomers in total) and each of them is sterically locked. They can be distinguished by NMR spectroscopy, and careful separation and crystallisation allow the two most abundant isomers to be isolated. Crystal structures and the absorption spectra of these two isomers are reported.
| Item Type: | Article |
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| Additional Information: | Supporting information: Additional data are given in the supplementary material. This material is available free of charge via the Internet at http://www.worldscientific.com/doi/suppl/10.1142/S108842462550049X. Crystallographic data have been deposited at the Cambridge Crystallographic Data Centre (CCDC) under the numbers CCDC-2425513 [3a] and CCDC-2425514[3b]. Copies can be obtained on request, free of charge, via https://www.ccdc.cam.ac.uk/structures. Acknowledgments: Support from EPSRC for X-ray crystallography equipment (grant number EP/S005854/1) is gratefully acknowledged. |
| Uncontrolled Keywords: | crystal structures,distortion,helical,phthalocyanines,stereoisomers,synthesis,twisted phthalocyanines,chemistry(all) ,/dk/atira/pure/subjectarea/asjc/1600 |
| Faculty \ School: | Faculty of Science > School of Chemistry, Pharmacy and Pharmacology |
| UEA Research Groups: | Faculty of Science > Research Groups > Centre for Photonics and Quantum Science Faculty of Science > Research Groups > Chemistry of Materials and Catalysis Faculty of Science > Research Groups > Chemistry of Light and Energy |
| Related URLs: | |
| Depositing User: | LivePure Connector |
| Date Deposited: | 22 May 2025 11:30 |
| Last Modified: | 28 May 2025 08:30 |
| URI: | https://ueaeprints.uea.ac.uk/id/eprint/99325 |
| DOI: | 10.1142/s108842462550049x |
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