Like hydroquinones and quinones, aromatic compounds with
multiple
NH2 groups and the corresponding quinonediimines have the
potential to serve as components of useful redox-active organic materials.
Benzene-1,2,4,5-tetramine (BTA) and its oxidized form BTA-H2 offer a promising redox pair of this type, and the compounds have
proven to be useful in many areas of chemistry. However, key aspects
of their behavior have remained poorly studied, such as the nature
of their protonated forms, their preferred molecular structures, their
reactivity, and their organization in condensed phases. In the present
work, we have used a combination of improved methods of synthesis,
computation, spectroscopic studies, and structural analyses to develop
a deeper understanding of BTA, BTA-H2, their salts, and
related compounds. The new knowledge is expected to accelerate exploitation
of the compounds in areas of materials science where desirable properties
can only be attained by properly controlling the organization of molecular
components.