Use of a 9,10-Dihydrofulvalene Pincer Cycloadduct as a Cornerstone for Molecular Architecture

Mirta Golić; Martin R. Johnston; Davor Margetić; Austin C. Schultz; Ronald N. Warrener

doi:10.1071/CH06286

RESEARCH ARTICLE

Use of a 9,10-Dihydrofulvalene Pincer Cycloadduct as a Cornerstone for Molecular Architecture

Mirta Golić ^A ^B , Martin R. Johnston ^A ^C ^G , Davor Margetić ^A ^D , Austin C. Schultz ^A ^E and Ronald N. Warrener ^A ^F

+ Author Affiliations

- Author Affiliations

^A Centre for Molecular Architecture, Central Queensland University, Rockhampton QLD 4700, Australia.

^B Innovation and Technical Centre, Peanut Company of Australia, PO Box 26, Kingaroy QLD 4610, Australia.

^C School of Chemistry, Physics and Earth Sciences, Flinders University, Adelaide SA 5042, Australia.

^D Laboratory for Physical Organic Chemistry, Department of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, 10000 Zagreb, Croatia.

^E Sugar Research Institute, Mackay QLD 4740, Australia.

^F Molecular Architecture Section, Intelligent Polymer Research Institute, University of Wollongong, Wollongong NSW 2522, Australia.

^G Corresponding author. Email: martin.johnston@flinders.edu.au

Australian Journal of Chemistry 59(12) 899-914 https://doi.org/10.1071/CH06286
Submitted: 11 August 2006 Accepted: 13 October 2006 Published: 20 December 2006

Abstract

Dimethyl-3,3a,3b,4,6a,7a-hexahydro-3,4,7-metheno-7H-cyclopenta[a]pentalene-7,8-dicarboxylate (3, a 9,10-dihydrofulvalene pincer cycloadduct) was found to be a versatile building block for the synthesis of polynorbornyl scaffolds containing various end functionalities such as porphyrins, pyrimidine, and the phenanthroline ligand in the free and complexed forms. The block is stable under various cycloaddition reaction conditions and has high π-bond reactivity. Molecular modelling using a semi-empirical based method (AM1) shows that incorporation of this diene block into polynorbornyl systems has an important influence on their overall architecture. In particular, incorporation of the block results in a straightening of the curvature normally observed in polynorbornyl molecules to form almost ideally linear polycyclic rigid spacers.

Acknowledgements

The authors are grateful for funding support from the Australian Research Council. M.R.J. thanks Central Queensland University for a Research Advancement Award.

References

Use of a 9,10-Dihydrofulvalene Pincer Cycloadduct as a Cornerstone for Molecular Architecture

Abstract

Acknowledgements

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