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

Holý, Petr; Havlík, Martin; Tichý, Miloš; Závada, Jiří; Císařová, Ivana

doi:10.1135/cccc20060139

CCCC > Archive > 2006, Volume 71 > Issue 2 > p. 139

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 Holý^a,*, Martin Havlík^a, Miloš Tichý^a, Jiří Závada^a,* and Ivana Císařová^b

^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

Abstract

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.

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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

Abstract