This project focuses on the synthesis and analysis of a series of sterically interesting molecules in the 14-aryl-14H-dibenzo[b,i]xanthene-1,6,8,13-tetraone (BNQ or binaphthoquinone) and 14-aryl-14H-dibenzo[a,j]xanthene (DBX or dibenzoxanthene) series. Such compounds may potentially serve as ligands in organometallic chemistry.<br/><br/>The synthesis of some of these compounds has been previously reported, but the unusual conditions reported have proven to be difficult to replicate. The current series is synthesized by Friedel-Crafts mechanisms in an acidic environment. The different substituents on the 14-phenyl ring alters the bond lengths and angles but has only a small effect on the electron density on the entire molecule. The 14-H sp3 hybridized hydrogen atom shifts in the Nuclear Magnetic Resonance (NMR) spectrum depending on the substituent group.<br/><br/>When the structure is confirmed by multi-nuclei NMR, it is then crystallized so X-ray diffraction crystallography can provide further information very accurately. Several examples of the halogen substituted DBX series have already been crystallized, demonstrating systematic changes in the unit cell and bond length parameters. This data will further the understanding of the structure-property relationships within these compounds and the potential use as ligands in organometallic sandwich complexes.

Large and affected by charge: Synthesis and analysis of binaphpthoquinone and dibenzoxanthene compounds

251st National Meeting (2016)

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