Trimeric anilines as both donors and acceptors: an experimental and computational study

A series of donor/acceptor complexes are formed using the TTF, TCNE, and TCNQ with substituted aniline trimers in dilute acetonitrile solutions to investigate the relative success of the trimers as either electron donors or acceptors. Likewise, the effect of protonation by hydrochloric acid on the aniline trimers is investigated. Experimental results are harmonized with the results of high level density functional calculations, which reveal that trimer anilines are fascinatingly useful reagents in their own right.