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

Rowland, Casey A.; Yap, Glenn A.; Bloch, Eric D.

doi:10.1039/d0dt01149e

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

Journal Article · Wed May 13 00:00:00 EDT 2020 · Dalton Transactions

DOI:https://doi.org/10.1039/d0dt01149e· OSTI ID:1848889

Rowland, Casey A. ^[1]; ^[2]; ^[2]

Univ. of Delaware, Newark, DE (United States); OSTI
Univ. of Delaware, Newark, DE (United States)

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.

View Accepted Manuscript (DOE)

Research Organization:: Univ. of Delaware, Newark, DE (United States)

Sponsoring Organization:: USDOE Office of Energy Efficiency and Renewable Energy (EERE); USDOE Office of Energy Efficiency and Renewable Energy (EERE), Transportation Office. Vehicle Technologies Office

Grant/Contract Number:: EE0008813

OSTI ID:: 1848889

Alternate ID(s):: OSTI ID: 1630225

Journal Information:: Dalton Transactions, Journal Name: Dalton Transactions Journal Issue: 45 Vol. 49; ISSN 1477-9226

Publisher:: Royal Society of ChemistryCopyright Statement

Country of Publication:: United States

Language:: English

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