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Issue 35, 2018
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Consistent supramolecular assembly arising from a mixture of components – self-sorting and solid solutions of chiral oxygenated trianglimines

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Abstract

The [3 + 3] cyclocondensation of either oxygen or methoxy group-containing terephthalaldehydes with optically pure vicinal diamines provides triangular macrocycles, whose constitution and symmetry depend on the structure of the aldehyde substrate. Formation of hexa-oxygenated trianglimine is highly stereoselective: that is, the use of racemic diamine yields a racemic mixture of homochiral triangular macrocycles, each having the same absolute configuration at all stereogenic centers. However, no self-sorting is observed when a mixture of non-, mono- and di-oxygenated dialdehydes is subjected to the cyclocondensation reaction with the optically pure diamine. In crystals, the variously oxygenated trianglimines consistently assemble into chiral columnar aggregates and form two- or three-component solid solutions. Some of these assemblies exhibit intracolumnar and/or intercolumnar inclusion properties. While the tris-oxygenated trianglimine crystallizes as a solid solution of molecular isomers, a mixture of uniformly chiral macrocycles that are built of variously oxygenated aldehyde sub-units provides a ternary solid solution deprived of any solvent molecules. For racemic trianglimine, formation of supramolecular columnar assemblies is accomplished by enantioselective self-recognition.

Graphical abstract: Consistent supramolecular assembly arising from a mixture of components – self-sorting and solid solutions of chiral oxygenated trianglimines

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Publication details

The article was received on 26 Jun 2018, accepted on 01 Aug 2018 and first published on 04 Aug 2018


Article type: Paper
DOI: 10.1039/C8CE01044G
Citation: CrystEngComm, 2018,20, 5200-5208
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    Consistent supramolecular assembly arising from a mixture of components – self-sorting and solid solutions of chiral oxygenated trianglimines

    J. Szymkowiak, B. Warżajtis, U. Rychlewska and M. Kwit, CrystEngComm, 2018, 20, 5200
    DOI: 10.1039/C8CE01044G

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