Synthesis of C₂-Symmetric pyrenophanes and aromatic belt precursors

Yang, Yixi (2010) Synthesis of C₂-Symmetric pyrenophanes and aromatic belt precursors. Masters thesis, Memorial University of Newfoundland.

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Abstract

The research described in this thesis mainly dealt with methodology development, design, synthesis as well as the study of the physical properties of new pyrenophanes and aromatic belt precursors cyclophanetetraene 4.16. The valence isomerization/dehydrogenation (VID) methodology was employed in all of the projects, to the synthesis of pyrenophanes with extended aromatic surfaces as well as ultimate goal: fully aromatic "Vögtle" type belts. -- Over the past several years, Bodwell's group has exploited a valence isomerization/dehydrogenation (VID) reaction, which can accomplish the formation of [n](2,7)pyrenophane with, nonplanar pyrene units. In all these cases, the pyrenophane is achiral. In Chapter 2, a C₂-symmetric, chiral pyrenophane, [10](1,6)pyrenophane was successfully synthesized using the VID reaction along with [10](1,8)pyrenophane. -- In addition, toward the synthesis of aromatic belt precursor cyclophanetetraene, two molecular boards were prepared in Chapter3. One large scaled (8 g) molecular board 3.11 which was obtained from m-xylene in 12 steps (6%). Another molecular board, which was not the intended target, was synthesized in 9 steps from 4-hydroxyisophthalic acid (14%) and this synthetic route could possibly be used to synthesize larger sized molecular boards. -- In Chapter 4, the large scaled molecular board 3.11 was used to covert to aromatic belt precursors. A straightforward synthetic plan for the synthesis of aromatic belts also is described in this Chapter.

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