Clockwise helical stacking of triphenylbenzene-based organogelator induced by peripheral chirality

We report on the synthesis and self-assembly of a new discotic organogelator based on pi-conjugated triphenylbenzene with three peripheral chiral substituents. It is found that the introduction of chiral groups to the C-3-symmetric molecule led to a hexagonal columnar chiral stacking of the molecules in a clockwise direction in the organogel fibers. And the fluorescent emission of the gel decreased significantly compared to the monomer state at the same concentration, as a result of the aggregation of the nonplanar triphenylbenzene core in the gel phase. (c) 2007 Elsevier Ltd. All rights reserved.