The primary objective of the present investigation was to study a class of compounds in which two donors and one acceptor (D2A) are parts of the same molecule: 3a-e. Systematic variation of the donor moiety (ArCH2; Ar = C6H5, p-MeOC6H4, p-NO2C6H4, β-naphthyl, p-NH2C6H4 (3a-e)) leads to a series of compounds that behave in solution to a large extent like substituted TCNQ molecules. In contrast, the isomorphous mode of aggregation in the solid state for 3a, 3b, and 3d indicates a strong driving force toward segregated stacking of the TCNQ moieties, a packing arrangement not observed in other TCNQ derivatives. The solid-state spectral properties also indicate the crucial role of the mode of aggregation. The relevance of these compounds to an overall strategy of design of organic conducting materials is discussed.
ASJC Scopus subject areas
- Organic Chemistry