Collect. Czech. Chem. Commun. 2001, 66, 820-832

Formation of Infinite Grids with Chiral Square Compartments by Self-Assembly of Achiral 1,1'-Biphenyl-2,2',6,6'-tetracarboxylic Acids. Effect of 4,4'-Substitution on the Grid Stacking

Petr Holýa, Jiří Závadaa,*, Josef Zezulaa, Ivana Císařováb and Jaroslav Podlahab

a Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 166 10 Prague 6, Czech Republic
b Charles University, Department of Inorganic Chemistry, 128 40 Prague 2, Czech Republic


The achiral 1,1'-biphenyl-2,2',6,6'-tetracarboxylic acid as well as its 4,4'-dibromo and 4,4'-dinitro derivative self-assemble in crystal under formation of a two-dimensional grid set up from hydrogen-bonded cyclotetrameric compartments which are individually chiral (D4 symmetry). The roughly square cavities (ca 5.6 Å) of individual compartments partly accommodate the perpendicularly oriented benzene rings of the neighbouring grid, in dependence on the nature of the 4,4'-substituents. As a consequence, the grids are stacked in a staggered (nonconcatenated) manner.

Keywords: Carboxylic acids; Crystal structure determination; Hydrogen bonds; Crystal engineering; Self assembly; Chiral porous solids; Biaryls; Biphenyls.

References: 27 live references.