A straightforward synthesis of triphenylene-perylene-triphenylene triad structures has been achieved by using versatile triphenylene intermediates bearing a single oxyalkyl amine side chain. Among these, PBITP(10) showed a stable columnar mesophase implying favorably matched core-core separations in the structure. Importantly, the triad can be used as a vehicle for doping columnar triphenylene matrices with functional but incompatible perylene units and a mixture of hexahexyloxytriphenylene matrix doped with 0.1% PBITP(10) is homogeneous and liquid crystalline.

Triphenylene twins are intriguing structures, and those bridged through their 3,6-positions by dipyrromethene units give a new class of macrocycles that can be viewed as rigid, expanded porphyrin derivatives in which coplanarity is enforced in a formally antiaromatic π system. Somewhat surprisingly, however, macrocyclization leads to significant overall stabilization of the dipyrromethene chromophores.