Template-Directed Assembly of a Macrocyclic Porphyrin Tetramer Using Olefin Metathesis

Jacinta M. Bakker; Steven J. Langford; Melissa J. Latter; Katrina A. Lee; Clint P. Woodward

doi:10.1071/CH05262

RESEARCH ARTICLE

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Template-Directed Assembly of a Macrocyclic Porphyrin Tetramer Using Olefin Metathesis

Jacinta M. Bakker ^A , Steven J. Langford ^A ^B , Melissa J. Latter ^A , Katrina A. Lee ^A and Clint P. Woodward ^A

+ Author Affiliations

- Author Affiliations

^A School of Chemistry, Monash University, Clayton VIC 3800, Australia.

^B Corresponding author. Email: steven.langford@sci.monash.edu.au

Australian Journal of Chemistry 58(11) 757-761 https://doi.org/10.1071/CH05262
Submitted: 24 September 2005 Accepted: 21 October 2005 Published: 9 December 2005

Abstract

A macrocyclic porphyrin tetramer was prepared in 52% yield by olefin metathesis employing a 5,10,15,20-tetrapyridylporphyrin template.

Acknowledgements

This work was supported by the Australian Research Council, Discovery Project Scheme through award to S.J.L. (DP0556313), which is greatfully acknowledged. We thank Dr P. Nichols and S. Duck for their help in obtaining NMR and mass spectra, respectively.

References

^* Oxidation of 4 to form 5 did not occur with Pb(OAc)₄ in CH₃CO₂H as outlined in the procedures of ref. [13]. Upon addition of catalytic quantities of Ac₂O to Pb(OAc)₄/CH₃CO₂H we obtained pyrrole 5 in high yields, as adopted from ref. [14]. We also observed formation of pyrrole 5 in good yield in the absence of Ac₂O however the reaction was heated at 80°C for 1.5 h to achieve this.

^† Attempts to image the free base of square 11 using STM techniques have not been successful. We have attributed this to the more flexible nature of 11 and the heptyl side chains. This view is supported by ref. [12f] where STM of a tetraphenylporphyrin analogue on highly ordered pyrolytic graphite was possible when the template porphyrin was complexed, providing a more rigid structure.

Template-Directed Assembly of a Macrocyclic Porphyrin Tetramer Using Olefin Metathesis

Abstract

Acknowledgements

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