Issue 45, 2020

Novel syntheses of carbazole-3,6-dicarboxylate ligands and their utilization for porous coordination cages

Abstract

The molecular nature, and thus potential solubility, of coordination cages endows them with a number of advantages as compared to metal–organic frameworks and other extended network solids. However, their lack of three-dimensional connectivity typically limits their thermal stability as inter-cage interactions in these materials are relatively weak. This is particularly the case for carbazole-based coordination cages. Here, we report the design and synthesis of a benzyl-functionalized octahedral coordination cage that displays moderate surface area and increased thermal stability as compared to its unfunctionalized counterpart. Structural analysis suggests the increased thermal stability is a result of aryl–aryl interactions between ligand groups on adjacent cages. We have further adapted the ligand synthesis strategy to afford a novel, high-yielding preparatory route for the isolation of carbazole-3,6-dicarboxylic acid that does not rely on pyrophoric reagents or transition metal catalysts.

Graphical abstract: Novel syntheses of carbazole-3,6-dicarboxylate ligands and their utilization for porous coordination cages

Supplementary files

Article information

Article type
Paper
Submitted
26 mar 2020
Accepted
13 mai 2020
First published
13 mai 2020

Dalton Trans., 2020,49, 16340-16347

Author version available

Novel syntheses of carbazole-3,6-dicarboxylate ligands and their utilization for porous coordination cages

C. A. Rowland, G. P. A. Yap and E. D. Bloch, Dalton Trans., 2020, 49, 16340 DOI: 10.1039/D0DT01149E

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