Synthesis of polyphenyl pyrenophanes and pyrenylene-ethynylene nanorings

Zhang, Baozhong (2007) Synthesis of polyphenyl pyrenophanes and pyrenylene-ethynylene nanorings. Doctoral (PhD) thesis, Memorial University of Newfoundland.

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Abstract

This thesis mainly describes the application of the valence isomerization-dehydrogenation (VID) reaction in the syntheses of cyclic pyrene-containing molecules. -- The pyrene-containing nanorings described in Chapter 2 are named pyrenophynes, which consist of ethylene bridges between each of the two aromatic units. These nanorings are analogs to Oda's para-phenylene-ethynylene derivatives. Several synthetic methods have been attempted. Although the final pyrenylene-ethylnylene nanorings have not been synthesized yet, the formation of a key intermediate tetrathiacyclophyne has been verified by experiment evidence and will be instructive to future research. -- In Chapter 3, the syntheses of pyrenophanes are made up of all aromatic units are described, including the pyrenophane with central para-phenylene, meta-phenylene, and 2,5-thienylene units. Müllen's methodology of building nanographitic sheets was adopted to construct the skeleton of these pyrenophanes. -- In Chapter 4, synthetic investigation focuses on extremely distorted aromatic systems. In order to achieve a more distorted (2,7)pyrenophane than all the previously synthesized ones in the Bodwell group, a series of octaphenyl pyrenophanes with a central aliphatic bridge were synthesized, and the most distorted (2,7)pyrenophane that has only 6 carbon atoms in the bridge was generated using the VID methodology.

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