Collect. Czech. Chem. Commun. 2006, 71, 139-154

Synthesis and Self-Assembly of 9,9'-Spirobifluorene-2,2',7,7'-tetracarboxylic Acid and Its Tetraamide. Non-Catenated Formation of Achiral Grid Layers with Large Chiral Pores

Petr Holýa,*, Martin Havlíka, Miloš Tichýa, Jiří Závadaa,* and Ivana Císařováb

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


The title tetrasubstituted spirobifluorenes 3a, 3b have been designed to serve as convenient achiral tectons for self-assembly of 2D layers with large chiral pores. The underlying stereochemical concept has been confirmed by the results of crystallographic analysis of tetraacid 3a. Self-assembly of isosteric tetraamide 3b led to markedly different results.

Keywords: Carboxylic acids; Spiro compounds; X-Ray diffraction; Hydrogen bonds; Supramolecular chemistry; Self assembly; Crystal engineering; Organic porous materials.

References: 42 live references.