Self-Assembly of 1,3,5-Benzenetricarboxylic (Trimesic) Acid and Its Analogues

Nature abhors a vacuum. Attempts to self-assemble nanoporous crystals (clathrates) with trimesic acid and its analogues reveal a striking variability in carboxylic acid motifs that often allow close-packing without clathrate formation. The common R22(8) carboxylic acid dimer is found in tributyl trimesic acid, which forms a “self-filled” two-dimensional chicken-wire network, and in 1, a mimic of trimesic acid dimer 2, which forms a similar network and a cavity clathrate.