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.
- Publication Date:
- Research Org.:
- Univ. of Delaware, Newark, DE (United States)
- Sponsoring Org.:
- USDOE Office of Energy Efficiency and Renewable Energy (EERE), Transportation Office. Vehicle Technologies Office; USDOE Office of Energy Efficiency and Renewable Energy (EERE)
- OSTI Identifier:
- 1848889
- Alternate Identifier(s):
- OSTI ID: 1630225
- Grant/Contract Number:
- EE0008813
- Resource Type:
- Accepted Manuscript
- Journal Name:
- Dalton Transactions
- Additional Journal Information:
- Journal Volume: 49; Journal Issue: 45; Journal ID: ISSN 1477-9226
- Publisher:
- Royal Society of Chemistry
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Citation Formats
Rowland, Casey A., Yap, Glenn A., and Bloch, Eric D. Novel syntheses of carbazole-3,6-dicarboxylate ligands and their utilization for porous coordination cages. United States: N. p., 2020.
Web. doi:10.1039/d0dt01149e.
Rowland, Casey A., Yap, Glenn A., & Bloch, Eric D. Novel syntheses of carbazole-3,6-dicarboxylate ligands and their utilization for porous coordination cages. United States. https://doi.org/10.1039/d0dt01149e
Rowland, Casey A., Yap, Glenn A., and Bloch, Eric D. Wed .
"Novel syntheses of carbazole-3,6-dicarboxylate ligands and their utilization for porous coordination cages". United States. https://doi.org/10.1039/d0dt01149e. https://www.osti.gov/servlets/purl/1848889.
@article{osti_1848889,
title = {Novel syntheses of carbazole-3,6-dicarboxylate ligands and their utilization for porous coordination cages},
author = {Rowland, Casey A. and Yap, Glenn A. and Bloch, Eric D.},
abstractNote = {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.},
doi = {10.1039/d0dt01149e},
journal = {Dalton Transactions},
number = 45,
volume = 49,
place = {United States},
year = {Wed May 13 00:00:00 EDT 2020},
month = {Wed May 13 00:00:00 EDT 2020}
}
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