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

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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

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Supplementary files

Article information


Submitted
26 Mar 2020
Accepted
13 May 2020
First published
13 May 2020

Dalton Trans., 2020, Advance Article
Article type
Paper

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, Advance Article , DOI: 10.1039/D0DT01149E

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