Tröger’s Base Chemistry in Solution and in Zr(IV)-Based Metal–Organic Frameworks

Gong, Wei; Kazem-Rostami, Masoud; Son, Florencia A.; Su, Shengyi; Fahy, Kira M.; Xie, Haomiao; Islamoglu, Timur; Liu, Yan; Stoddart, J. Fraser; Cui, Yong; Farha, Omar K.

doi:10.1021/jacs.2c08623

Tröger’s Base Chemistry in Solution and in Zr(IV)-Based Metal–Organic Frameworks

Journal Article · 01 December 2022 · Journal of the American Chemical Society

DOI:https://doi.org/10.1021/jacs.2c08623· OSTI ID:2419251

^[1]; ^[2]; ^[2]; ^[2]; ^[2]; ^[2]; ^[2]; ^[3]; ^[4]; ^[3]; ^[5]

School of Chemistry and Chemical Engineering, Frontiers Science Center for Transformative Molecules and State Key Laboratory of Metal Matrix Composites, Shanghai Jiao Tong University, Shanghai 200240, China; Department of Chemistry and International Institute for Nanotechnology (IIN), Northwestern University, Evanston, Illinois 60208, United States; OSTI
Department of Chemistry and International Institute for Nanotechnology (IIN), Northwestern University, Evanston, Illinois 60208, United States
School of Chemistry and Chemical Engineering, Frontiers Science Center for Transformative Molecules and State Key Laboratory of Metal Matrix Composites, Shanghai Jiao Tong University, Shanghai 200240, China
Department of Chemistry and International Institute for Nanotechnology (IIN), Northwestern University, Evanston, Illinois 60208, United States; School of Chemistry, University of New South Wales, Sydney, NSW 2052, Australia; Stoddart Institute of Molecular Science, Department of Chemistry, Zhejiang University, Hangzhou 310021, China; ZJU-Hangzhou Global Scientific and Technological Innovation Center, Hangzhou 311215, China
Department of Chemistry and International Institute for Nanotechnology (IIN), Northwestern University, Evanston, Illinois 60208, United States; Department of Chemical & Biological Engineering, Northwestern University, Evanston, Illinois 60208, United States

Not provided.

Research Organization:: Northwestern Univ., Evanston, IL (United States)

Sponsoring Organization:: USDOE Office of Science (SC)

DOE Contract Number:: FG02-08ER15967

OSTI ID:: 2419251

Journal Information:: Journal of the American Chemical Society, Journal Name: Journal of the American Chemical Society Journal Issue: 49 Vol. 144; ISSN 0002-7863

Publisher:: American Chemical Society (ACS)

Country of Publication:: United States

Language:: English

References (51)

Zirconium-Based Metal–Organic Frameworks for the Catalytic Hydrolysis of Organophosphorus Nerve Agents Kirlikovali, Kent O.; Chen, Zhijie; Islamoglu, Timur ACS Applied Materials & Interfaces, Vol. 12, Issue 13 https://doi.org/10.1021/acsami.9b20154	journal	January 2020
Controlled Exchange of Achiral Linkers with Chiral Linkers in Zr-Based UiO-68 Metal–Organic Framework Tan, Chunxia; Han, Xing; Li, Zijian Journal of the American Chemical Society, Vol. 140, Issue 47 https://doi.org/10.1021/jacs.8b09606	journal	October 2018
Geometry Mismatch and Reticular Chemistry: Strategies To Assemble Metal–Organic Frameworks with Non-default Topologies Guillerm, Vincent; Maspoch, Daniel Journal of the American Chemical Society, Vol. 141, Issue 42 https://doi.org/10.1021/jacs.9b08754	journal	September 2019
Synthesis and properties of a new series of trögerophanes Ibrahim, Alhussein A.; Matsumoto, Mutsumi; Miyahara, Yuji Journal of Heterocyclic Chemistry, Vol. 35, Issue 1 https://doi.org/10.1002/jhet.5570350139	journal	January 1998
Synthesis and structural characterisation of a Co(II) coordination polymer incorporating a novel dicarboxy-Trögers base/bis-pyrazole mixed ligand system Hawes, Chris S.; Fitchett, Christopher M.; Batten, Stuart R. Inorganica Chimica Acta, Vol. 389 https://doi.org/10.1016/j.ica.2012.01.046	journal	July 2012
Synthesis of Chiral Carbo-Nanotweezers for Enantiospecific Recognition and DNA Duplex Winding in Cancer Cells Tripathi, Indu; Misra, Santosh K.; Ostadhossein, Fatemeh ACS Applied Materials & Interfaces, Vol. 10, Issue 44 https://doi.org/10.1021/acsami.8b15618	journal	October 2018
Modulated self-assembly of metal–organic frameworks Forgan, Ross S. Chemical Science, Vol. 11, Issue 18 https://doi.org/10.1039/D0SC01356K	journal	January 2020
Synthesis, Characterization, and Anticancer Activity of Novel Macrocyclic Indenedione Based on the Tröger’s Base and N,N′-Disubstituted Phenhomazine Candidates Ibrahim, A. A.; Mohamed, S. F.; El-Hashash, M. A. Russian Journal of General Chemistry, Vol. 90, Issue 9 https://doi.org/10.1134/S1070363220090224	journal	September 2020
Optically active and photoswitchable Tröger's base analogs Kazem-Rostami, Masoud New Journal of Chemistry, Vol. 43, Issue 20 https://doi.org/10.1039/C9NJ01372E	journal	January 2019
Enantiospecific Recognition of DNA Sequences by a Proflavine Tröger Base Bailly, Christian; Laine, William; Demeunynck, Martine Biochemical and Biophysical Research Communications, Vol. 273, Issue 2 https://doi.org/10.1006/bbrc.2000.2997	journal	July 2000
A New Zirconium Inorganic Building Brick Forming Metal Organic Frameworks with Exceptional Stability Cavka, Jasmina Hafizovic; Jakobsen, Søren; Olsbye, Unni Journal of the American Chemical Society, Vol. 130, Issue 42, p. 13850-13851 https://doi.org/10.1021/ja8057953	journal	October 2008
New Chiral Molecular Tweezers with a Bis-Tröger's Base Skeleton Pardo, Carmen; Sesmilo, Esther; Gutiérrez-Puebla, Enrique The Journal of Organic Chemistry, Vol. 66, Issue 5 https://doi.org/10.1021/jo0010882	journal	February 2001
A structural study of Troger's base scaffold-based dyes for DSSC applications Urnikaite, Simona; Braukyla, Titas; Magomedov, Artiom Dyes and Pigments, Vol. 143 https://doi.org/10.1016/j.dyepig.2017.04.012	journal	August 2017
A Tröger’s Base-Derived Covalent Organic Polymer Containing Carbazole Units as a High-Performance Supercapacitor EL-Mahdy, Ahmed F. M.; Lüder, Johann; Kotp, Mohammed G. Polymers, Vol. 13, Issue 9 https://doi.org/10.3390/polym13091385	journal	April 2021
Topology-Based Functionalization of Robust Chiral Zr-Based Metal–Organic Frameworks for Catalytic Enantioselective Hydrogenation Jiang, Hong; Zhang, Wenqiang; Kang, Xing Journal of the American Chemical Society https://doi.org/10.1021/jacs.0c00637	journal	May 2020
Structural Diversity of Zirconium Metal–Organic Frameworks and Effect on Adsorption of Toxic Chemicals Chen, Yongwei; Zhang, Xuan; Mian, Mohammad Rasel Journal of the American Chemical Society, Vol. 142, Issue 51 https://doi.org/10.1021/jacs.0c10400	journal	December 2020
The Structure of Troeger's Base Spielman, M. A. Journal of the American Chemical Society, Vol. 57, Issue 3 https://doi.org/10.1021/ja01306a060	journal	March 1935
Synthesis and Characterization of Macrocyclic Chiral Tröger’s Base Phenhomazine Candidates as Anticancer Agent Ibrahim, Alhussein A.; Ali, Korany A.; Hafez, Naglaa A. Abdel Frontiers in Chemistry, Vol. 8 https://doi.org/10.3389/fchem.2020.633065	journal	January 2021
Tröger's‐Base‐Derived Infinite Co‐ordination Polymer Microparticles Jeon, You‐Moon; Armatas, Gerasimos S.; Kim, Dongwoo Small, Vol. 5, Issue 1 https://doi.org/10.1002/smll.200801160	journal	January 2009
Molecular recognition: Chain length selectivity studies of dicarboxylic acids by the cavity of a new Troger's base receptor Goswami, Shyamaprosad; Ghosh, Kumaresh Tetrahedron Letters, Vol. 38, Issue 25 https://doi.org/10.1016/S0040-4039(97)00914-3	journal	June 1997
A Flexible Metal–Organic Framework with 4-Connected Zr ₆ Nodes Zhang, Yuanyuan; Zhang, Xuan; Lyu, Jiafei Journal of the American Chemical Society, Vol. 140, Issue 36 https://doi.org/10.1021/jacs.8b06789	journal	August 2018
H2-selective Troger's base polymer based mixed matrix membranes enhanced by 2D MOFs Deng, Jing; Dai, Zhongde; Deng, Liyuan Journal of Membrane Science, Vol. 610 https://doi.org/10.1016/j.memsci.2020.118262	journal	September 2020
Symmetrical and Nonsymmetrical Chromophores with Tröger’s Base Skeleton: Chiroptical, Linear, and Quadratic Nonlinear Optical Properties—A Joint Theoretical and Experimental Study Sergeyev, Sergey; Didier, Delphine; Boitsov, Vitaly Chemistry – A European Journal, Vol. 16, Issue 27 https://doi.org/10.1002/chem.201000216	journal	July 2010
A Desymmetrization Route to Fused Tröger's Base Analogues: Synthesis, Isolation, and Characterization of the First Anti-Anti Diastereomer of a Fused Tris-Tröger's Base Analogue Hansson, Anna; Wixe, Torbjörn; Bergquist, Karl-Erik Organic Letters, Vol. 7, Issue 10 https://doi.org/10.1021/ol050513g	journal	May 2005
Ligand-Directed Reticular Synthesis of Catalytically Active Missing Zirconium-Based Metal–Organic Frameworks Chen, Zhijie; Li, Penghao; Wang, Xingjie Journal of the American Chemical Society, Vol. 141, Issue 31 https://doi.org/10.1021/jacs.9b06179	journal	July 2019
Novel heterocyclic Tröger's base derivatives containing N-methylpyrrole units Valı&#x;k, Martin; Dolensky, Bohumil; Petřı&#x;čková, Hana Tetrahedron Letters, Vol. 44, Issue 10 https://doi.org/10.1016/S0040-4039(03)00177-1	journal	March 2003
Tröger’s Base Twisted Amides: Endo Functionalization and Synthesis of an Inverted Crown Ether Artacho, Josep; Ascic, Erhad; Rantanen, Toni Organic Letters, Vol. 14, Issue 18 https://doi.org/10.1021/ol302022y	journal	September 2012
Troeger's base. An alternate synthesis and a structural analog with thromboxane A2 synthetase inhibitory activity Johnson, Roy A.; Gorman, Robert R.; Wnuk, Richard J. Journal of Medicinal Chemistry, Vol. 36, Issue 21 https://doi.org/10.1021/jm00073a023	journal	October 1993
The 125^th Anniversary of the Tröger's Base Molecule: Synthesis and Applications of Tröger's Base Analogues Rúnarsson, Ögmundur Vidar; Artacho, Josep; Wärnmark, Kenneth European Journal of Organic Chemistry, Vol. 2012, Issue 36 https://doi.org/10.1002/ejoc.201201249	journal	November 2012
Structure of 5,11-methano-2,8-dimethyl-5,6,11,12-tetrahydrodibenzo[b,f][1,5]diazocine (Tröger's base) at 163 K Larson, S. B.; Wilcox, C. S. Acta Crystallographica Section C Crystal Structure Communications, Vol. 42, Issue 2 https://doi.org/10.1107/S0108270186096713	journal	February 1986
Stereoselective Mannich reactions catalyzed by Tröger’s base derivatives in aqueous media Wu, Hui; Chen, Xiu-mei; Wan, Yu Tetrahedron Letters, Vol. 50, Issue 9 https://doi.org/10.1016/j.tetlet.2008.12.067	journal	March 2009
Thiourea derivatives of Tröger’s base: synthesis, enantioseparation and evaluation in organocatalysis of Michael addition to nitroolefins Sergeyev, Sergey; Didier, Delphine Arkivoc, Vol. 2009, Issue 14 https://doi.org/10.3998/ark.5550190.0010.e12	journal	February 2010
Synthesis of 5,6,11,12-tetrahydrodibenzo[b,f][1,5]diazocines and a demonstration of their reactivity to afford methano strap-modified Tröger’s base analogues Mahon, Andrew B.; Craig, Donald C.; Try, Andrew C. Arkivoc, Vol. 2008, Issue 12 https://doi.org/10.3998/ark.5550190.0009.c17	journal	April 2008
Crystal structures and solid-state fluorescence of BODIPY dyes based on Λ-shaped Tröger's base Xi, He; Yuan, Chun-Xue; Li, Ye-Xin CrystEngComm, Vol. 14, Issue 6 https://doi.org/10.1039/c2ce06260g	journal	January 2012
Water Sorption Evolution Enabled by Reticular Construction of Zirconium Metal–Organic Frameworks Based on a Unique [2.2]Paracyclophane Scaffold Gong, Wei; Xie, Haomiao; Idrees, Karam B. Journal of the American Chemical Society, Vol. 144, Issue 4 https://doi.org/10.1021/jacs.1c11836	journal	January 2022
Ueber einige mittelst nascirenden Formaldehydes entstehende Basen Tröger, Julius Journal für Praktische Chemie, Vol. 36, Issue 1 https://doi.org/10.1002/prac.18870360123	journal	September 1887
Innovative Multipodal Ligands Derived from Tröger's Bases for the Sensitization of Lanthanide(III) Luminescence Trupp, Leandro; Bruttomesso, Andrea C.; Vardé, Mariana Chemistry – A European Journal, Vol. 26, Issue 70 https://doi.org/10.1002/chem.202003524	journal	November 2020
N-Centered Chiral Self-Sorting and Supramolecular Helix of Tröger's Base-Based Dimeric Macrocycles in Crystalline State Chen, Yuan; Cheng, Ming; Hong, Benkun Frontiers in Chemistry, Vol. 7 https://doi.org/10.3389/fchem.2019.00383	journal	May 2019
Self‐Discriminating Self‐Assembly of Dinuclear Heterochiral Rhombs from Tröger’s Base Derived Bis(pyridyl) Ligands Weilandt, Torsten; Kiehne, Ulf; Bunzen, Jens Chemistry – A European Journal, Vol. 16, Issue 8 https://doi.org/10.1002/chem.200902993	journal	February 2010
Troger's Base Molecular Scaffolds in Dicarboxylic Acid Recognition Goswami, Shyamaprosad; Ghosh, Kumaresh; Dasgupta, Swagata The Journal of Organic Chemistry, Vol. 65, Issue 7 https://doi.org/10.1021/jo9909204	journal	March 2000
A New Entry to Bis‐Tröger’s Bases Mas, Thierry; Pardo, Carmen; Salort, Francisca European Journal of Organic Chemistry, Vol. 2004, Issue 5 https://doi.org/10.1002/ejoc.200300645	journal	February 2004
Clusters with a Zr6O8 core Schubert, Ulrich Coordination Chemistry Reviews, Vol. 469 https://doi.org/10.1016/j.ccr.2022.214686	journal	October 2022
Introduction to Reticular Chemistry Yaghi, Omar M.; Kalmutzki, Markus J.; Diercks, Christian S. Wiley‐VCH Verlag GmbH & Co. https://doi.org/10.1002/9783527821099	journal	January 2019
Synthesis, Photophysical, and DNA Binding Studies of Fluorescent Tröger’s Base Derived 4-Amino-1,8-naphthalimide Supramolecular Clefts Veale, Emma B.; Gunnlaugsson, Thorfinnur The Journal of Organic Chemistry, Vol. 75, Issue 16 https://doi.org/10.1021/jo1005697	journal	July 2010
Nanofiltration membranes from crosslinked Troger's base Polymers of Intrinsic Microporosity (PIMs) Agarwal, Praveen; Hefner, Robert E.; Ge, Shouren Journal of Membrane Science, Vol. 595 https://doi.org/10.1016/j.memsci.2019.117501	journal	February 2020
Diastereoselective Self-Assembly of Double-Stranded Helicates from Tröger's Base Derivatives Kiehne, U.; Weilandt, T.; Lützen, A. Organic Letters, Vol. 9, Issue 7 https://doi.org/10.1021/ol070048i	journal	March 2007
Synthesis of Symmetric Diester‐Functionalised Tröger's Base Analogues Bhuiyan, M. Delower H.; Zhu, Kai‐Xian; Jensen, Paul European Journal of Organic Chemistry, Vol. 2010, Issue 24 https://doi.org/10.1002/ejoc.201000086	journal	July 2010
An Efficient Polymer Molecular Sieve for Membrane Gas Separations Carta, M.; Malpass-Evans, R.; Croad, M. Science, Vol. 339, Issue 6117, p. 303-307 https://doi.org/10.1126/science.1228032	journal	January 2013
Supramolecular Approach to Enantioselective DNA Recognition Using Enantiomerically Resolved Cationic 4-Amino-1,8-naphthalimide-Based Tröger’s Bases Banerjee, Swagata; Bright, Sandra A.; Smith, Jayden A. The Journal of Organic Chemistry, Vol. 79, Issue 19 https://doi.org/10.1021/jo501711g	journal	September 2014
Oligo Tröger's bases—new molecular scaffolds Dolenský, Bohumil; Havlík, Martin; Král, Vladimír Chemical Society Reviews, Vol. 41, Issue 10 https://doi.org/10.1039/c2cs15307f	journal	January 2012
Proton Conduction in Tröger’s Base-Linked Poly(crown ether)s Patel, Hasmukh A.; Selberg, John; Salah, Dhafer ACS Applied Materials & Interfaces, Vol. 10, Issue 30 https://doi.org/10.1021/acsami.8b05532	journal	June 2018

Similar Records

Reticular Chemistry in Its Chiral Form: Axially Chiral Zr(IV)-Spiro Metal–Organic Framework as a Case Study

Journal Article · 2023 · Journal of the American Chemical Society · OSTI ID:2419253

Programmed Polarizability Engineering in a Cyclen-Based Cubic Zr(IV) Metal–Organic Framework to Boost Xe/Kr Separation

Journal Article · 2023 · Journal of the American Chemical Society · OSTI ID:2419252

Reticular Chemistry in Pore Engineering of a Y-Based Metal–Organic Framework for Xenon/Krypton Separation

Journal Article · 2023 · ACS Applied Materials and Interfaces · OSTI ID:2419248

Related Subjects

Chemistry

Tröger’s Base Chemistry in Solution and in Zr(IV)-Based Metal–Organic Frameworks

Citation Formats

References (51)

Similar Records

Related Subjects