Hinged bis-porphyrin scaffolds I. The synthesis of a new porphyrin diene and its role in constructing hinged porphyrin dyads and cavity systems
✍ Scribed by Hesheng Tang; Zemin Dong; Zul Merican; Davor Margetić; Željko Marinić; Maxwell J. Gunter; David Officer; Douglas N. Butler; Ronald N. Warrener
- Book ID
- 104096074
- Publisher
- Elsevier Science
- Year
- 2009
- Tongue
- French
- Weight
- 339 KB
- Volume
- 50
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
Norbornene building BLOCKs formed by the reaction of porphyrin 1,3-dienes with norbornadiene or dimethyl tricyclo[4.2.1.0 2,5 ]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 16r-bonds. The ability of the doubly hinged ZnPOR-16r-ZnPOR scaffold to adopt cavity-shaped conformations was indicated by semiempirical AM1 calculations of these conformationally flexible bis-porphyrin scaffolds.