Effect of BN/CC Isosterism on the Thermodynamics of Surface and Bulk Binding: 1,2-Dihydro-1,2-azaborine vs Benzene

Abstract

The chemistry of organoboron compounds has long been dominated by their high reactivity in synthetic organic chemistry. Recently, the incorporation of boron as a structural element in compounds has led to an increased diversity of organic compounds. A promising method of boron incorporation is BN/CC isosterism, where the replacement of a CC unit of the ubiquitous arene, benzene, with the isolectronic BN unit results in azaborine compounds whose properties are intermediate between benzene and borazine. These conjugated boron–nitrogen-containing heteroatom compounds show potential for use as charge transport materials in organic electronic devices in which the molecule–contact interface is a crucial factor of device performance. Therefore, to gain a fundamental understanding of the interaction of azaborines with two common metals, we examined 1,2-dihydro-1,2-azaborine and benzene desorption from Au(111) and Cu(111) by temperature-programmed desorption (TPD). Scanning tunneling microscopy imaging and theoret...