Derivatives of relatively electron rich 1,5-dialkoxynaphthalene (Dan) donors and relatively electrondeficient 1,4,5,8-naphthalenetetracarboxylic diimide (Ndi) acceptors have been exploited in the folding andself-assembly of a variety of complex molecular systems in solution. Here, we report the use of Dan andNdi derivatives to direct assembly of extended columns with alternating face-centered stacked structure inthe solid state. A variety of 1:1 Dan:Ndi mixtures produced mesophases that were found to be stable overtemperature ranges extending up to 110
C. Analysis of these mesophases indicates mixtures with soft/plastic crystal phases and a few mixtures with the thermodynamic properties of true liquid crystals, allcomposed of alternating donor-acceptor columns within. Importantly, a correspondence was found betweenthe clearing and crystallization points of the mesophase mixtures and the melting/clearing points of thecomponent Ndi and Dan units, respectively. This correspondence enables the predictable tuning ofmesophase phase transition temperatures. The study of sterically hindered derivatives led to a set of mixturesin which a dramatic and sudden color change (deep red to yellow) was observed upon crystallization ofthe mesophase due to a phase separation of the component donor and acceptor units.