Polyaromatic hydrocarbons (PAH's) have been of interest recently because of their ability to form columnar super structures. PAH’s are commonly used as analogues of graphene in a variety of organic electronic devices including injection layers and solar cells. These subunits arrange into disk-like configurations and form their columnar superstructures which then rearrange into hexagonal mesophases. With a variety of heteroatom substitutions, PAH's have shown a range of chemical and physical properties. Such compounds may also have the ability to coordinate to zero-valent metal centers to form a new class of sandwich complexes. A series of 14-phenyl-14H-dibenzo[a,j]xanthene (DBX) complexes were formed and this synthetic approach was extended to the synthesis of a series of 14-phenyl-14H-dibenzo[a,j]xanthenylium cation species (DBX+). With this series of DBX+ complexes the closed the system was formed and created a series of benzo[5,6]naphthacene[1,12,11,10-jklmna]xanthylium(BNCX) according to the methodology of Wu and Meuller. This yielded a variety of BNCX analogues. Substituents including nitro- or bromo- groups influence the geometry and electronic properties of the molecule. Using Nuclear Magnetic Resonance (NMR) the location and interaction between the atoms within the structure was measured. Single crystal X-ray diffraction was used to measure the bond lengths and angles within the structure. The sp3 hybridized proton (14-H) appeared at 6.46 ppm in CDCl3 in the 14-phenyl DBX and was seen to shift upon formation of the DBX+ analogue. These compounds are of interest for their potential use as ligands within organometallic complexes.

Heteroatom polyaromatic hydrocarbon systems with nitrogen ligands

251st National Meeting (2016)

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