Design and synthesis of aryl-functionalized carbazole-based porous coordination cages

Rowland, Casey A.; Lorzing, Gregory R.; Bhattacharjee, Rameswar; Caratzoulas, Stavros; Yap, Glenn P. A.; Bloch, Eric D.

doi:10.1039/d0cc03910a

Title: Design and synthesis of aryl-functionalized carbazole-based porous coordination cages

Journal Article · Fri Jul 03 00:00:00 EDT 2020 · ChemComm

DOI:https://doi.org/10.1039/d0cc03910a· OSTI ID:1801384

Rowland, Casey A. ^[1]; Lorzing, Gregory R. ^[2];

^[3]; Caratzoulas, Stavros ^[3];

^[1];

^[4]

Univ. of Delaware, Newark, DE (United States). Dept. of Chemistry and Biochemistry
Univ. of Delaware, Newark, DE (United States). Dept. of Chemistry and Biochemistry. Center for Neutron Science. Dept. of Chemical and Biomolecular Engineering
Univ. of Delaware, Newark, DE (United States). Catalysis Center for Energy Innovation (CCEI)
Univ. of Delaware, Newark, DE (United States). Dept. of Chemistry and Biochemistry. Center for Neutron Science. Dept. of Chemical and Biomolecular Engineering. Catalysis Center for Energy Innovation (CCEI)

A subset of coordination cages have garnered considerable recent attention for their potential permanent porosity in the solid state. Herein, we report a series of functionalized carbazole-based cages of the structure type M₁₂(R-cdc)₁₂ (M = Cr, Cu, Mo) where the functional groups include a range of aromatic substituents. Single-crystal X-ray structure determinations reveal a variety of intercage interactions in these materials, largely governed by pi–pi stacking. Density functional theory for a subset of these cages was used to confirm that the nature of the increased stability of aryl-functionalized cages is a result of inter-cage ligand interactions.

View Accepted Manuscript (DOE)

Cite

Export

Save

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

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES)

Grant/Contract Number:: SC0001004; AC02-06CH11357

OSTI ID:: 1801384

Alternate ID(s):: OSTI ID: 1638754

Journal Information:: ChemComm, Vol. 56, Issue 65; ISSN 1359-7345

Publisher:: Royal Society of ChemistryCopyright Statement

Country of Publication:: United States

Language:: English

Citation Metrics:

Cited by: 8 works

Citation information provided by
Web of Science

References (29)

Chromium(II) Metal–Organic Polyhedra as Highly Porous Materials Park, Jinhee; Perry, Zachary; Chen, Ying-Pin ACS Applied Materials & Interfaces, Vol. 9, Issue 33 https://doi.org/10.1021/acsami.7b09339	journal	August 2017
Ligand-Based Phase Control in Porous Molecular Assemblies Barreda, Omar; Bannwart, Gianluca; Yap, Glenn P. A. ACS Applied Materials & Interfaces, Vol. 10, Issue 14 https://doi.org/10.1021/acsami.8b02015	journal	March 2018
Porous organic cages Tozawa, Tomokazu; Jones, James T. A.; Swamy, Shashikala I. Nature Materials, Vol. 8, Issue 12, p. 973-978 https://doi.org/10.1038/nmat2545	journal	October 2009
Surface functionalization of metal–organic polyhedron for homogeneous cyclopropanation catalysis Lu, Weigang; Yuan, Daqiang; Yakovenko, Andrey Chemical Communications, Vol. 47, Issue 17 https://doi.org/10.1039/c1cc00030f	journal	January 2011
Design and Synthesis of Porous Nickel(II) and Cobalt(II) Cages Gosselin, Eric J.; Rowland, Casey A.; Balto, Krista P. Inorganic Chemistry, Vol. 57, Issue 19 https://doi.org/10.1021/acs.inorgchem.8b01130	journal	May 2018
A metal–organic framework with a 9-phenylcarbazole moiety as a fluorescent tag for picric acid explosive detection: collaboration of electron transfer, hydrogen bonding and size matching Jiang, Xiaoli; Liu, Yanhong; Wu, Pengyan RSC Adv., Vol. 4, Issue 88 https://doi.org/10.1039/C4RA07067D	journal	January 2014
Adsorption Contraction Mechanics: Understanding Breathing Energetics in Isoreticular Metal–Organic Frameworks Krause, Simon; Evans, Jack D.; Bon, Volodymyr The Journal of Physical Chemistry C, Vol. 122, Issue 33 https://doi.org/10.1021/acs.jpcc.8b04549	journal	July 2018
A pressure-amplifying framework material with negative gas adsorption transitions Krause, Simon; Bon, Volodymyr; Senkovska, Irena Nature, Vol. 532, Issue 7599 https://doi.org/10.1038/nature17430	journal	April 2016
Methane Storage in Paddlewheel-Based Porous Coordination Cages Rowland, Casey A.; Lorzing, Gregory R.; Gosselin, Eric J. Journal of the American Chemical Society, Vol. 140, Issue 36 https://doi.org/10.1021/jacs.8b05780	journal	August 2018
Metal–organic polyhedra constructed from dinuclear ruthenium paddlewheels Young, Mark D.; Zhang, Qiang; Zhou, Hong-Cai Inorganica Chimica Acta, Vol. 424 https://doi.org/10.1016/j.ica.2014.09.010	journal	January 2015
Understanding Gas Storage in Cuboctahedral Porous Coordination Cages Lorzing, Gregory R.; Gosselin, Eric J.; Trump, Benjamin A. Journal of the American Chemical Society, Vol. 141, Issue 30 https://doi.org/10.1021/jacs.9b05872	journal	July 2019
Oriented Controllable Fabrication of Metal–Organic Frameworks Membranes as Solid Catalysts for Cascade Indole Acylation–Nazarov Cyclization for Cyclopentenone[ b ]indoles Huang, Chao; Zhang, Yingying; Yang, Haiyan Crystal Growth & Design, Vol. 18, Issue 9 https://doi.org/10.1021/acs.cgd.8b01050	journal	August 2018
Metal-organic polyhedra 18 mixed-matrix membranes for gas separation Perez, Edson V.; Balkus, Kenneth J.; Ferraris, John P. Journal of Membrane Science, Vol. 463 https://doi.org/10.1016/j.memsci.2014.03.045	journal	August 2014
Highly efficient photocatalytic hydrogen production from pure water via a photoactive metal–organic framework and its PDMS@MOF Wu, Pengyan; Jiang, Min; Li, Yang Journal of Materials Chemistry A, Vol. 5, Issue 17 https://doi.org/10.1039/C7TA01070B	journal	January 2017
Suprasupermolecular Chemistry: Infinite Networks from Nanoscale Metal−Organic Building Blocks ^† McManus, Gregory J.; Wang, Zhenqiang; Zaworotko, Michael J. Crystal Growth & Design, Vol. 4, Issue 1 https://doi.org/10.1021/cg034199d	journal	January 2004
Azobenzene-Functionalized Metal-Organic Polyhedra for the Optically Responsive Capture and Release of Guest Molecules Park, Jinhee; Sun, Lin-Bing; Chen, Ying-Pin Angewandte Chemie International Edition, Vol. 53, Issue 23 https://doi.org/10.1002/anie.201310211	journal	May 2014
Rhodium–Organic Cuboctahedra as Porous Solids with Strong Binding Sites Furukawa, Shuhei; Horike, Nao; Kondo, Mio Inorganic Chemistry, Vol. 55, Issue 21 https://doi.org/10.1021/acs.inorgchem.6b02091	journal	October 2016
The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: two new functionals and systematic testing of four M06-class functionals and 12 other functionals Zhao, Yan; Truhlar, Donald G. Theoretical Chemistry Accounts, Vol. 120, Issue 1-3 https://doi.org/10.1007/s00214-007-0310-x	journal	July 2007
CO ₂ capture in a carbazole-based supramolecular polyhedron structure: the significance of Cu( ii ) open metal sites López-Olvera, Alfredo; Sánchez-González, Elí; Campos-Reales-Pineda, Alberto Inorganic Chemistry Frontiers, Vol. 4, Issue 1 https://doi.org/10.1039/C6QI00342G	journal	January 2017
Porous Metal−Organic Polyhedra: 25 Å Cuboctahedron Constructed from 12 Cu₂(CO₂)₄ Paddle-Wheel Building Blocks Eddaoudi, M.; Kim, Jaheon; Wachter, J. B. Journal of the American Chemical Society, Vol. 123, Issue 18, p. 4368-4369 https://doi.org/10.1021/ja0104352	journal	May 2001
Porous organic molecular solids by dynamic covalent scrambling Jiang, Shan; Jones, James T. A.; Hasell, Tom Nature Communications, Vol. 2, Issue 1 https://doi.org/10.1038/ncomms1207	journal	February 2011
MOF-mimetic molecules: carboxylate-based supramolecular complexes as molecular metal–organic framework analogues Decker, Gerald E.; Lorzing, Gregory R.; Deegan, Meaghan M. Journal of Materials Chemistry A, Vol. 8, Issue 8 https://doi.org/10.1039/C9TA12497G	journal	January 2020
Stabilizing Metal–Organic Polyhedra (MOP): Issues and Strategies Mollick, Samraj; Fajal, Sahel; Mukherjee, Soumya Chemistry – An Asian Journal, Vol. 14, Issue 18 https://doi.org/10.1002/asia.201900800	journal	August 2019
Discovery and introduction of a (3,18)-connected net as an ideal blueprint for the design of metal–organic frameworks Guillerm, Vincent; Weseliński, Łukasz J.; Belmabkhout, Youssef Nature Chemistry, Vol. 6, Issue 8 https://doi.org/10.1038/nchem.1982	journal	June 2014
Reticular Chemistry of Metal–Organic Polyhedra Tranchemontagne, David J.; Ni, Zheng; O'Keeffe, Michael Angewandte Chemie International Edition, Vol. 47, Issue 28, p. 5136-5147 https://doi.org/10.1002/anie.200705008	journal	June 2008
Interconversion between Molecular Polyhedra and Metal−Organic Frameworks Li, Jian-Rong; Timmons, Daren J.; Zhou, Hong-Cai Journal of the American Chemical Society, Vol. 131, Issue 18 https://doi.org/10.1021/ja901731z	journal	May 2009
Ligand Bridging-Angle-Driven Assembly of Molecular Architectures Based on Quadruply Bonded Mo−Mo Dimers Li, Jian-Rong; Yakovenko, Andrey A.; Lu, Weigang Journal of the American Chemical Society, Vol. 132, Issue 49 https://doi.org/10.1021/ja1080794	journal	December 2010
Design and synthesis of capped-paddlewheel-based porous coordination cages Lorzing, Gregory R.; Gosselin, Eric J.; Lindner, Brian S. Chemical Communications, Vol. 55, Issue 64 https://doi.org/10.1039/C9CC05002G	journal	January 2019
High-Symmetry Coordination Cages via Self-Assembly Seidel, S. Russell; Stang, Peter J. Accounts of Chemical Research, Vol. 35, Issue 11 https://doi.org/10.1021/ar010142d	journal	November 2002

Linked Research (8)

Similar Records

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 · OSTI ID:1801384

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

Hydrogen Storage in Porous Cages

Journal Article · Mon Nov 07 00:00:00 EST 2022 · ACS Materials Au · OSTI ID:1801384

Deegan, Meaghan M.; Lorzing, Gregory R.; Korman, Kyle J.; +4 more

Synthesis, characterization, and polymerization of capped paddlewheel porous cages

Journal Article · Thu Feb 04 00:00:00 EST 2021 · Dalton Transactions · OSTI ID:1801384

Deegan, Meaghan M.; Bloch, Eric D.

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

CCDC 1833902: Experimental Crystal Structure Determination A., Rowland, Casey; R., Lorzing, Gregory; Rameswar, Bhattacharjee, https://doi.org/10.5517/ccdc.csd.cc1zkb40 The current record is supplemented by this dataset	dataset	January 2020
CCDC 1941343: Experimental Crystal Structure Determination A., Rowland, Casey; R., Lorzing, Gregory; Rameswar, Bhattacharjee, https://doi.org/10.5517/ccdc.csd.cc2353zd The current record is supplemented by this dataset	dataset	January 2020
CCDC 1941344: Experimental Crystal Structure Determination A., Rowland, Casey; R., Lorzing, Gregory; Rameswar, Bhattacharjee, https://doi.org/10.5517/ccdc.csd.cc23540g The current record is supplemented by this dataset	dataset	January 2020
CCDC 1941345: Experimental Crystal Structure Determination A., Rowland, Casey; R., Lorzing, Gregory; Rameswar, Bhattacharjee, https://doi.org/10.5517/ccdc.csd.cc23541h The current record is supplemented by this dataset	dataset	January 2020
CCDC 1941346: Experimental Crystal Structure Determination A., Rowland, Casey; R., Lorzing, Gregory; Rameswar, Bhattacharjee, https://doi.org/10.5517/ccdc.csd.cc23542j The current record is supplemented by this dataset	dataset	January 2020
CCDC 1941347: Experimental Crystal Structure Determination A., Rowland, Casey; R., Lorzing, Gregory; Rameswar, Bhattacharjee, https://doi.org/10.5517/ccdc.csd.cc23543k The current record is supplemented by this dataset	dataset	January 2020
CCDC 1950221: Experimental Crystal Structure Determination A., Rowland, Casey; R., Lorzing, Gregory; Rameswar, Bhattacharjee, https://doi.org/10.5517/ccdc.csd.cc23gccb The current record is supplemented by this dataset	dataset	January 2020
CCDC 1961488: Experimental Crystal Structure Determination A., Rowland, Casey; R., Lorzing, Gregory; Rameswar, Bhattacharjee, https://doi.org/10.5517/ccdc.csd.cc23v2tw The current record is supplemented by this dataset	dataset	January 2020

Title: Design and synthesis of aryl-functionalized carbazole-based porous coordination cages

Citation Formats

References (29)

Linked Research (8)

Similar Records

Related Subjects