Synthesis of heterocyclic aromatic compounds has been pursued for a long time by chemists in order to analyze their properties and potential applications in biomedical and materials sciences including electronic devices such as organic light emitting devices (OLEDs) and in hydrogen storage.

The compound 1,2-dihydro-1,2-azaborine was first synthesized in 2008 after almost forty years of failed attempts. 1,2-dihydro-1,2-azaborine is isoelectric with benzene in that it has the same number of valence electrons and the same atomic connectivity as benzene, but it contains boron and nitrogen atoms in place of two carbons. Its properties were investigated and this heterocycle has similar aromatic properties to benzene and even has a similar smell. It is now being investigated to aid in synthesis of boron-based pharmacophores, markers, and neutron-capture agents for biomedical use and boron-based optoelectronic and hydrogen-storage compounds for materials science applications. The analogous boron-sulfur heterocycle 2H-1,2-thiaborin should be similarly interesting for investigating its chemical properties.

Researchers at the University of Michigan designed a synthetic route to make the first monocyclic 2H-1,2-thiaborin analog 2-(diisopropylamino)-2H-1,2-thaiborin in 15% yield. Spectroscopic and structural analysis showed that this compound has limited aromatic character. In addition, the pi-interaction of the exocyclic amino substituent with boron diminishes the endocyclic pi-bonding ability expected for the parent ring. As 2H-1,2-thiaborins are closely related to aromatic hydrocarbons, derivatives of 2H-1,2-thiaborins may be used in similar manner as polycyclic aromatic hydrocarbons in photovoltaics and transistors.

Potential applications for these new synthetic compounds include their use in various electronic devices such as organic light emitting diodes (OLEDs), hydrogen storage devices, and as a synthetic route to other boron-sulfur containing devices.

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This article first appeared in the March, 2012 issue of Lighting Technology Magazine.

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