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Hinged bis-porphyrin scaffolds I. The synthesis of a new porphyrin diene and its role in constructing hinged porphyrin dyads and cavity systems |
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| Authors: | Hesheng Tang Zul Merican ?eljko Marini? David Officer Ronald N Warrener |
| Institution: | a Centre for Molecular Architecture, Central Queensland University, Rockhampton, Queensland 4702, Australia b Molecular Architecture Section, Intelligent Polymer Research Institute, University of Wollongong, Northfields Avenue, Wollongong, NSW 2522, Australia c Laboratory for Physical Organic Chemistry, Department of Organic Chemistry and Biochemistry, Ru?er Boškovi? Institute, Bijeni?ka c. 54, 10000 Zagreb, Croatia d The University of New England, School of Biological, Biomedical and Molecular Sciences, Armidale, NSW 2351, Australia e Nanomaterials Research Centre, Massey University, Private Bag 11-222, Palmerston North, New Zealand f Centre for NMR, Ru?er Boškovi? Institute, Bijeni?ka c. 54, 10000 Zagreb, Croatia |
| Abstract: | Norbornene building BLOCKs formed by the reaction of porphyrin 1,3-dienes with norbornadiene or dimethyl tricyclo4.2.1.02,5]nona-2,7-diene-3,4-dicarboxylate were coupled with an ester-activated cyclobutene epoxide BLOCK to afford the first examples of hinged porphyrin-spacer-acceptor dyads. Similar dual coupling with a bis-(cyclobutene epoxide) formed doubly hinged POR-spacer-POR scaffolds separated by up to 16σ-bonds. The ability of the doubly hinged ZnPOR-16σ-ZnPOR scaffold to adopt cavity-shaped conformations was indicated by semiempirical AM1 calculations of these conformationally flexible bis-porphyrin scaffolds. |
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