Oxidative homo-coupling reactions of aryl boronic acids using a porous copper metal-organic framework as a highly efficient heterogeneous catalyst

Yaghi, Omar M.; Czaja, Alexander U.; Wang, Bo; Lu, Zheng

Title: Oxidative homo-coupling reactions of aryl boronic acids using a porous copper metal-organic framework as a highly efficient heterogeneous catalyst

Patent · Tue Jun 02 00:00:00 EDT 2015

OSTI ID:1183458

Yaghi, Omar M.; Czaja, Alexander U.; Wang, Bo; Lu, Zheng

The disclosure provides methods for the use of open metal frameworks to catalyze coupling reactions.

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Research Organization:: Univ. of California, Oakland, CA (United States)

Sponsoring Organization:: USDOE

DOE Contract Number:: FG02-08ER15935

Assignee:: The Regents of the University of California (Oakland, CA)

Patent Number(s):: 9,045,387

Application Number:: 13/387,598

OSTI ID:: 1183458

Country of Publication:: United States

Language:: English

References (142)

Process for Manufacture of Olefin Oxides Berg, Clyde H.O. https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/2684967 US Patent Document 2,684,967	patent	July 1954
Preparation of metal-containing zeolite catalysts of increased stability and activity Tsao, Ying-Yen P.; Wong, Stephen S. https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/4532225 US Patent Document 4,532,225	patent	July 1985
Zeolite synthesis using an alcohol or like molecules Chu, Pochen; Klocke, Donald J.; Marler, David O. https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/5160500 US Patent Document 5,160,500	patent	November 1992
Reversible oxygen sorbent compositions Ramprasad, Dorai; Pez, Guido P.; Pearlstein, Ronald Martin https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/5208335 US Patent Document 5,208,335	patent	May 1993
Crystalline metal-organic microporous materials Yaghi, Omar M. https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/5648508 US Patent Document 5,648,508	patent	July 1997
Non-regenerating carbon monoxide sensor Goldstein, Mark K.; Taniguchi, Vernon T.; Helfman, William B. https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/5733505 US Patent Document 5,733,505	patent	March 1998
Bleaching composition for dry cleaning containing transition metal bleach catalyst Bijl, Dirk Johannes; Hage, Ronald; Kevelam, Jan https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/6479447 US Patent Document 6,479,447	patent	November 2002
Late transition metal catalyst complexes and oligomers therefrom Stibrany, Robert T.; Matturro, Michael G.; Zushma, Stephen https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/6501000 US Patent Document 6,501,000	patent	December 2002
Process for producing polyalkylene carbonates Müller, Ulrich; Luinstra, Gerrit; Yaghi, Omar M. https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/6617467 US Patent Document 6,617,467	patent	September 2003
Process for the epoxidation of an organic compound with oxygen or an oxygen-delivering compounds using catalysts containing metal-organic frame-work materials Müller, Ulrich; Lobree, Lisa; Hesse, Michael https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/6624318 US Patent Document 6,624,318	patent	September 2003
Metal catalyzed reactions Zhang, Xumu; Lei, Aiwen https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/6686428 US Patent Document 6,686,428	patent	February 2004
Shaped bodies containing metal-organic frameworks Mueller, Ulrich; Lobree, Lisa; Hesse, Michael https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/6893564 US Patent Document 6,893,564	patent	May 2005
Method of storing, uptaking, releasing of gases by novel framework materials Müller, Ulrich; Harth, Klaus; Hölzle, Markus https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/6929679 US Patent Document 6,929,679	patent	August 2005
Isoreticular metal-organic frameworks, process for forming the same, and systematic design of pore size and functionality therein, with application for gas storage Yaghi, Omar M.; Eddaoudi, Mohamed; Li, Hailian https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/6930193 US Patent Document 6,930,193	patent	August 2005
Isoreticular metal-organic frameworks, process for forming the same, and systematic design of pore size and functionality therein, with application for gas storage Yaghi, Omar M.; Eddaoudi, Mohamed; Li, Hailian https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/7196210 US Patent Document 7,196,210	patent	March 2007
Process for the alkoxylation of monools in the presence of metallo-organic framework materials Mueller, Ulrich; Metelkina, Olga; Hesse, Michael https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/7202385 US Patent Document 7,202,385	patent	April 2007
Process for the alkoxylation of organic compounds in the presence of novel framework materials Mueller, Ulrich; Stoesser, Michael; Ruppel, Raimund https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/7279517 US Patent Document 7,279,517	patent	October 2007
Gas storage system Müller, Ulrich; Hesse, Michael; Heβ, Reinhard https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/7309380 US Patent Document 7,309,380	patent	December 2007
Metal-organic framework materials for gaseous hydrocarbon storage Müller, Ulrich; Hesse, Michael; Putter, Hermann https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/7343747 US Patent Document 7,343,747	patent	March 2008
Process for preparing and organometallic framework material Mueller, Ulrich; Lippert, Gerald; Schubert, Olga https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/7411081 US Patent Document 7,411,081	patent	August 2008
Shaped bodies containing metal-organic frameworks Hesse, Michael; Mueller, Ulrich; Yaghi, Omar M. https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/7524444 US Patent Document 7,524,444	patent	April 2009
Covalently linked organic frameworks and polyhedra Yaghi, Omar M.; Matzger, Adam J.; Benin, Annabelle I. https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/7582798 US Patent Document 7,582,798	patent	September 2009
Implementation of a strategy for achieving extraordinary levels of surface area and porosity in crystals Yaghi, Omar M.; Matzger, Adam J.; Rowsell, Jesse L. C. https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/7652132 US Patent Document 7,652,132	patent	January 2010
High gas adsorption metal-organic framework Yaghi, Omar M.; Chen, Banglin https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/7662746 US Patent Document 7,662,746	patent	February 2010
Metal-organic frameworks with exceptionally high capacity for storage of carbon dioxide at room-temperature Yaghi, Omar M.; Millward, Andrew https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/7799120 US Patent Document 7,799,120	patent	September 2010
Porous organo-metallic skeleton material containing an additional polymer Mueller, Ulrich; Hesse, Michael; Schubert, Markus https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/7815716 US Patent Document 7,815,716	patent	October 2010
Gas sensor incorporating a porous framework Yaghi, Omar M.; Czaja, Alexander U.; Wang, Bo https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/8480955 US Patent Document 8,480,955	patent	July 2013
Reversible ethylene oxide capture in porous frameworks Yaghi, Omar M.; Britt, David K.; Czaja, Alexander U. https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/8709134 US Patent Document 8,709,134	patent	April 2014
Gas sensor incorporating a porous framework Yaghi, Omar M.; Czaja, Alexander U.; Wang, Bo https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/8735161 US Patent Document 8,735,161	patent	May 2014
Preparation of metal-catecholate frameworks Yaghi, Omar M.; Gandara-Barragan, Felipe; Lu, Zheng-Hong https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/8742152 US Patent Document 8,742,152	patent	June 2014
Isoreticular metal-organic frameworks, process for forming the same, and systematic design of pore size and functionality therein, with application for gas storage Yaghi, Omar M.; Eddaoudi, Mohamed; Li, Hailian https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20030004364 US Patent Application 10/137043; 20030004364	patent-application	January 2003
Process for the alkoxylation of organic compounds in the presence of novel framework materials Muller, Ulrich; Stober, Michael; Ruppel, Raimund https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20030078311 US Patent Application 10/039733; 20030078311	patent-application	April 2003
Method of storing, uptaking, releasing of gases by novel framework materials Muller, Ulrich; Harth, Klaus; Holzle, Markus https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20030148165 US Patent Application 10/061147; 20030148165	patent-application	August 2003
Shaped bodies containing metal-organic frameworks Mueller, Ulrich; Lobree, Lisa; Hesse, Michael https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20030222023 US Patent Application 10/157182; 20030222023	patent-application	December 2003
Process for preparing hydrogen peroxide from the elements Muller, Ulrich; Metelkina, Olga; Junicke, Henrik https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20040081611 US Patent Application 10/280013; 20040081611	patent-application	April 2004
Implementation of a strategy for achieving extraordinary levels of surface area and porosity in crystals Yaghi, Omar M.; Matzger, Adam J.; Rowsell, Jesse L.C. https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20040225134 US Patent Application 10/841983; 20040225134	patent-application	November 2004
Process for the alkoxylation of organic compounds in the presence of novel framework materials Mueller, Ulrich; Stober, Michael; Ruppel, Raimund https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20040249189 US Patent Application 10/492192; 20040249189	patent-application	December 2004
Gas storage system Muller, Ulrich; Hesse, Michael; Hess, Reinhard https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20040265670 US Patent Application 10/608146; 20040265670	patent-application	December 2004
Process for the alkoxylation of monools in the presence of metallo-organic framework materials Muller, Ulrich; Metelkina, Olga; Hesse, Michael https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20050004404 US Patent Application 10/611863; 20050004404	patent-application	January 2005
Crystalline membranes Tsapatsis, Michael; Lai, Zhiping https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20050014371 US Patent Application 10/794483; 20050014371	patent-application	January 2005
Metal-organic polyhedra Yaghi, Omar M.; Sudik, Andrea C. https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20050124819 US Patent Application 11/004696; 20050124819	patent-application	June 2005
Process for preparing an organometallic framework material Muller, Ulrich; Lippert, Gerald; Schubert, Olga https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20050154222 US Patent Application 10/755231; 20050154222	patent-application	July 2005
Isoreticular metal-organic frameworks, process for forming the same, and systematic design of pore size and functionality therein, with application for gas storage Yaghi, Omar M.; Eddaoudi, Mohamed; Li, Hailian https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20050192175 US Patent Application 11/119563; 20050192175	patent-application	September 2005
Process for preparing hydrogen peroxide from the elements Muller, Ulrich; Metelkina, Olga; Junicke, Henrik https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20060057057 US Patent Application 11/258265; 20060057057	patent-application	March 2006
Process for the alkoxylation of monools in the presence of metallo-organic framework materials Mueller, Ulrich; Metelkina, Olga; Hesse, Michael https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20060135824 US Patent Application 11/285070; 20060135824	patent-application	June 2006
Covalently linked organic frameworks and polyhedra Yaghi, Omar M.; Matzger, Adam J.; Benin, Annabelle https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20060154807 US Patent Application 11/256859; 20060154807	patent-application	July 2006
Metal-organic framework materials for gaseous hydrocarbon storage Muller, Ulrich; Hesse, Michael; Puetter, Hermann https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20060185388 US Patent Application 11/062861; 20060185388	patent-application	August 2006
High gas adsorption in a microporous metal-organic framework with open-metal sites Yaghi, Omar; Chen, Banglin https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20060252641 US Patent Application 11/400478; 20060252641	patent-application	November 2006
Adsorption process with on-line adsorbent removal Pilliod, Dana Lynn; Randall, Katy Conley; Harding, Eric Martin https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20060252972 US Patent Application 11/122312; 20060252972	patent-application	November 2006
Zeolite-like metal organic frameworks (ZMOFS): modular approach to the synthesis of organic-inorganic hybrid porous materials having a zeolite like topology Eddaoudi, Mohamed; Liu, Yunling https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20060287190 US Patent Application 11/410359; 20060287190	patent-application	December 2006
Metal-organic frameworks with exceptionally high capacity for storage of carbon dioxide at room-temperature Yaghi, Omar M. https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20070068389 US Patent Application 11/527232; 20070068389	patent-application	March 2007
PREPARATION OF FUNCTIONALIZED ZEOLITIC FRAMEWORKS Yaghi, Omar M.; Hayashi, Hideki; Banerjee, Rahul https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20070202038 US Patent Application 11/680386; 20070202038	patent-application	August 2007
Adsorbing Agent, Dust Collection Chamber And Method For Adsorbing Odours Schultink, Jan; Sauer, Ralf https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20080017036 US Patent Application 10/590175; 20080017036	patent-application	January 2008
Mesh-Adjustable Molecular Sieve Zhou, Hong-Cai; Ma, Shengqian https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20080184883 US Patent Application 11/738730; 20080184883	patent-application	August 2008
SHAPED BODIES CONTAINING METAL-ORGANIC FRAMEWORKS Hesse, Michael; Mueller, Ulrich; Yaghi, Omar https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20090155588 US Patent Application 12/372118; 20090155588	patent-application	June 2009
ADSORPTIVE GAS SEPARATION OF MULTI-COMPONENT GASES Yaghi, Omar M.; Hayashi, Hideki; Banerjee, Rahul https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20100132549 US Patent Application 12/598855; 20100132549	patent-application	June 2010
CRYSTALLINE 3D- AND 2D COVALENT ORGANIC FRAMEWORKS Yaghi, Omar M.; Cote, Adrien P.; El-Kaderi, Hani M. https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20100143693 US Patent Application 12/524205; 20100143693	patent-application	June 2010
PREPARATION OF FUNCTIONALIZED ZEOLITIC FRAMEWORKS Yaghi, Omar M.; Furukawa, Hiroyasu; Wang, Bo https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20100186588 US Patent Application 12/669616; 20100186588	patent-application	July 2010
EDIBLE AND BIOCOMPATIBLE METAL-ORGANIC FRAMEWORKS Yaghi, Omar M.; El-Kadri, Oussama M.; Fang, Qianrong https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20100286022 US Patent Application 12/680141; 20100286022	patent-application	November 2010
CHEMICAL FRAMEWORK COMPOSITIONS AND METHODS OF USE Yaghi, Omar M.; Li, Qiaowei; Miljanic, Ognjen S. https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20110137025 US Patent Application 12/996378; 20110137025	patent-application	June 2011
Mechanism of the Palladium-Catalyzed Homocoupling of Arylboronic Acids: Key Involvement of a Palladium Peroxo Complex Adamo, Carlo; Amatore, Christian; Ciofini, Ilaria Journal of the American Chemical Society, Vol. 128, Issue 21 https://doi.org/10.1021/ja0569959	journal	May 2006
Palladium-Catalyzed Suzuki-Type Self-Coupling of Arylboronic Acids. A Mechanistic Study Moreno-Mañas, Marcial; Pérez, Montserrat; Pleixats, Roser The Journal of Organic Chemistry, Vol. 61, Issue 7 https://doi.org/10.1021/jo9514329	journal	January 1996
Aryl−Aryl Bond Formation One Century after the Discovery of the Ullmann Reaction Hassan, Jwanro; Sévignon, Marc; Gozzi, Christel Chemical Reviews, Vol. 102, Issue 5, p. 1359-1470 https://doi.org/10.1021/cr000664r	journal	May 2002
Post-Synthetic Modification of Tagged Metal-Organic Frameworks Burrows, Andrew D.; Frost, Christopher G.; Mahon, Mary F. Angewandte Chemie International Edition, Vol. 47, Issue 44, p. 8482-8486 https://doi.org/10.1002/anie.200802908	journal	October 2008
High-Throughput Synthesis of Zeolitic Imidazolate Frameworks and Application to CO₂ Capture Banerjee, Rahul; Phan, Anh; Wang, Bo Science, Vol. 319, Issue 5865, p. 939-943 https://doi.org/10.1126/science.1152516	journal	February 2008
Control of Pore Size and Functionality in Isoreticular Zeolitic Imidazolate Frameworks and their Carbon Dioxide Selective Capture Properties Banerjee, Rahul; Furukawa, Hiroyasu; Britt, David Journal of the American Chemical Society, Vol. 131, Issue 11, p. 3875-3877 https://doi.org/10.1021/ja809459e	journal	March 2009
Azulene based metal–organic frameworks for strong adsorption of H₂ Barman, Samir; Furukawa, Hiroyasu; Blacque, Olivier Chemical Communications, Vol. 46, Issue 42, p. 7981-7983 https://doi.org/10.1039/c0cc02589e	journal	January 2010
Tailored Porous Materials Barton, Thomas J.; Bull, Lucy M.; Klemperer, Walter G. Chemistry of Materials, Vol. 11, Issue 10, p. 2633-2656 https://doi.org/10.1021/cm9805929	journal	October 1999
Metal Insertion in a Microporous Metal−Organic Framework Lined with 2,2′-Bipyridine Bloch, Eric D.; Britt, David; Lee, Chain Journal of the American Chemical Society, Vol. 132, Issue 41, p. 14382-14384 https://doi.org/10.1021/ja106935d	journal	October 2010
1,4-Benzenedicarboxylate derivatives as links in the design of paddle-wheel units and metal–organic frameworks Braun, Matthew E.; Steffek, Cory D.; Kim, Jaheon Chemical Communications, Vol. 0, Issue 24, p. 2532-2533 https://doi.org/10.1039/b108031h	journal	November 2001
Highly efficient separation of carbon dioxide by a metal-organic framework replete with open metal sites Britt, D.; Furukawa, H.; Wang, B. Proceedings of the National Academy of Sciences, Vol. 106, Issue 49, p. 20637-20640 https://doi.org/10.1073/pnas.0909718106	journal	November 2009
Ring-Opening Reactions within Porous Metal−Organic Frameworks Britt, David; Lee, Chain; Uribe-Romo, Fernando J. Inorganic Chemistry, Vol. 49, Issue 14, p. 6387-6389 https://doi.org/10.1021/ic100652x	journal	July 2010
Nanoporous three-dimensional networks topologically related to Cooperite from the self-assembly of copper(I) centres and the "‘square-planar’' building block 1,2,4,5-tetracyanobenzene Carlucci, Lucia; Ciani, Gianfranco; W.v. Gudenberg, Dorothea New Journal of Chemistry, Vol. 23, Issue 4, p. 397-402 https://doi.org/10.1039/a809144g	journal	January 1999
Polycatenation, polythreading and polyknotting in coordination network chemistry Carlucci, Lucia; Ciani, Gianfranco; Proserpio, Davide M. Coordination Chemistry Reviews, Vol. 246, Issue 1-2, p. 247-289 https://doi.org/10.1016/S0010-8545(03)00126-7	journal	November 2003
Dramatic Tuning of Carbon Dioxide Uptake via Metal Substitution in a Coordination Polymer with Cylindrical Pores Caskey, Stephen R.; Wong-Foy, Antek G.; Matzger, Adam J. Journal of the American Chemical Society, Vol. 130, Issue 33, p. 10870-10871 https://doi.org/10.1021/ja8036096	journal	August 2008
Raman spectra of hydrogen and deuterium adsorbed on a metal–organic framework Centrone, Andrea; Siberio-Pérez, Diana Y.; Millward, Andrew R. Chemical Physics Letters, Vol. 411, Issue 4-6, p. 516-519 https://doi.org/10.1016/j.cplett.2005.06.069	journal	August 2005
Tertiary Building Units: Synthesis, Structure, and Porosity of a Metal−Organic Dendrimer Framework (MODF-1) Chae, Hee K.; Eddaoudi, Mohamed; Kim, Jaheon Journal of the American Chemical Society, Vol. 123, Issue 46, p. 11482-11483 https://doi.org/10.1021/ja011692+		October 2001
MOFs as catalysts: Activity, reusability and shape-selectivity of a Pd-containing MOF Llabrés i Xamena, Françesc X.; Abad, Alberto; Corma, Avelino Journal of Catalysis, Vol. 250, Issue 2, p. 294-298 https://doi.org/10.1016/j.jcat.2007.06.004	journal	September 2007
A route to high surface area, porosity and inclusion of large molecules in crystals Chae, Hee K.; Siberio-Pérez, Diana Y.; Kim, Jaheon Nature, Vol. 427, Issue 6974, p. 523-527 https://doi.org/10.1038/nature02311	journal	February 2004
Cu₂(ATC)·6H₂O: Design of Open Metal Sites in Porous Metal−Organic Crystals (ATC: 1,3,5,7-Adamantane Tetracarboxylate) Chen, Banglin; Eddaoudi, M.; Reineke, T. M. Journal of the American Chemical Society, Vol. 122, Issue 46, p. 11559-11560 https://doi.org/10.1021/ja003159k	journal	November 2000
Interwoven Metal-Organic Framework on a Periodic Minimal Surface with Extra-Large Pores Chen, Banglin; Eddaoudi, M.; Hyde, S. T. Science, Vol. 291, Issue 5506, p. 1021-1023 https://doi.org/10.1126/science.1056598	journal	February 2001
Transformation of a Metal−Organic Framework from the NbO to PtS Net Chen, Banglin; Ockwig, Nathan W.; Fronczek, Frank R. Inorganic Chemistry, Vol. 44, Issue 2, p. 181-183 https://doi.org/10.1021/ic048612y	journal	January 2005
High H₂ Adsorption in a Microporous Metal-Organic Framework with Open Metal Sites Chen, Banglin; Ockwig, Nathan W.; Millward, Andrew R. Angewandte Chemie International Edition, Vol. 44, Issue 30, p. 4745-4749 https://doi.org/10.1002/anie.200462787	journal	July 2005
A Microporous Metal–Organic Framework for Gas-Chromatographic Separation of Alkanes Chen, Banglin; Liang, Chengdu; Yang, Jun Angewandte Chemie International Edition, Vol. 45, Issue 9, p. 1390-1393 https://doi.org/10.1002/anie.200502844	journal	February 2006
A metal–organic framework material that functions as an enantioselective catalyst for olefin epoxidation Cho, So-Hye; Ma, Baoqing; Nguyen, SonBinh T. Chem. Commun., Vol. 0, Issue 24, p. 2563-2565 https://doi.org/10.1039/B600408C	journal	January 2006
Heterogeneity within Order in Crystals of a Porous Metal–Organic Framework Choi, Kyung Min; Jeon, Hyung Joon; Kang, Jeung Ku Journal of the American Chemical Society, Vol. 133, Issue 31, p. 11920-11923 https://doi.org/10.1021/ja204818q	journal	August 2011
In Situ Hydrothermal Growth of Metal−Organic Framework 199 Films on Stainless Steel Fibers for Solid-Phase Microextraction of Gaseous Benzene Homologues Cui, Xiao-Yan; Gu, Zhi-Yuan; Jiang, Dong-Qing Analytical Chemistry, Vol. 81, Issue 23, p. 9771-9777 https://doi.org/10.1021/ac901663x	journal	December 2009
Three-periodic nets and tilings: regular and quasiregular nets Delgado Friedrichs, Olaf; O'Keeffe, Michael; Yaghi, Omar M. Acta Crystallographica Section A Foundations of Crystallography, Vol. 59, Issue 1, p. 22-27 https://doi.org/10.1107/S0108767302018494	journal	December 2002
What do we know about three-periodic nets? Delgado-Friedrichs, Olaf; Foster, Martin D.; O’Keeffe, Michael Journal of Solid State Chemistry, Vol. 178, Issue 8, p. 2533-2554 https://doi.org/10.1016/j.jssc.2005.06.037	journal	August 2005
Three-periodic nets and tilings: edge-transitive binodal structures Delgado-Friedrichs, Olaf; O'Keeffe, Michael; Yaghi, Omar M. Acta Crystallographica Section A Foundations of Crystallography, Vol. 62, Issue 5, p. 350-355 https://doi.org/10.1107/S0108767306022707	journal	August 2006
Multiple Functional Groups of Varying Ratios in Metal-Organic Frameworks Deng, H.; Doonan, C. J.; Furukawa, H. Science, Vol. 327, Issue 5967, p. 846-850 https://doi.org/10.1126/science.1181761	journal	February 2010
Robust dynamics Deng, Hexiang; Olson, Mark A.; Stoddart, J. Fraser Nature Chemistry, Vol. 2, Issue 6, p. 439-443 https://doi.org/10.1038/nchem.654	journal	May 2010
Isoreticular Metalation of Metal−Organic Frameworks Doonan, Christian J.; Morris, William; Furukawa, Hiroyasu Journal of the American Chemical Society, Vol. 131, Issue 27, p. 9492-9493 https://doi.org/10.1021/ja903251e	journal	July 2009
Design of New Materials for Methane Storage Düren, Tina; Sarkisov, Lev; Yaghi, Omar M. Langmuir, Vol. 20, Issue 7, p. 2683-2689 https://doi.org/10.1021/la0355500	journal	March 2004
Highly Porous and Stable Metal−Organic Frameworks: Structure Design and Sorption Properties Eddaoudi, Mohamed; Li, Hailian; Yaghi, O. M. Journal of the American Chemical Society, Vol. 122, Issue 7, p. 1391-1397 https://doi.org/10.1021/ja9933386	journal	February 2000
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
Modular Chemistry: Secondary Building Units as a Basis for the Design of Highly Porous and Robust Metal−Organic Carboxylate Frameworks Eddaoudi, Mohamed; Moler, David B.; Li, Hailian Accounts of Chemical Research, Vol. 34, Issue 4, p. 319-330 https://doi.org/10.1021/ar000034b	journal	April 2001
Geometric requirements and examples of important structures in the assembly of square building blocks Eddaoudi, M.; Kim, J.; Vodak, D. Proceedings of the National Academy of Sciences, Vol. 99, Issue 8, p. 4900-4904 https://doi.org/10.1073/pnas.082051899	journal	April 2002
Systematic Design of Pore Size and Functionality in Isoreticular MOFs and Their Application in Methane Storage Eddaoudi, Mohamed; Kim, Jaheon; Rosi, Nathaniel Science, Vol. 295, Issue 5554, p. 469-472 https://doi.org/10.1126/science.1067208	journal	January 2002
Cu₂[o-Br-C₆H₃(CO₂)₂]₂(H₂O)₂·(DMF)₈(H₂O)₂: A Framework Deliberately Designed To Have the NbO Structure Type Eddaoudi, Mohamed; Kim, Jaheon; O'Keeffe, Michael Journal of the American Chemical Society, Vol. 124, Issue 3, p. 376-377 https://doi.org/10.1021/ja017154e	journal	January 2002
Positronium formation in porous materials for antihydrogen production Ferragut, R.; Calloni, A.; Dupasquier, A. Journal of Physics: Conference Series, Vol. 225, Issue 1, Article No. 012007 https://doi.org/10.1088/1742-6596/225/1/012007	journal	April 2010
Independent verification of the saturation hydrogen uptake in MOF-177 and establishment of a benchmark for hydrogen adsorption in metal–organic frameworks Furukawa, Hiroyasu; Miller, Michael A.; Yaghi, Omar M. Journal of Materials Chemistry, Vol. 17, Issue 30, p. 3197-3204 https://doi.org/10.1039/b703608f	journal	January 2007
Control of Vertex Geometry, Structure Dimensionality, Functionality, and Pore Metrics in the Reticular Synthesis of Crystalline Metal−Organic Frameworks and Polyhedra Furukawa, Hiroyasu; Kim, Jaheon; Ockwig, Nathan W. Journal of the American Chemical Society, Vol. 130, Issue 35, p. 11650-11661 https://doi.org/10.1021/ja803783c	journal	September 2008
Storage of Hydrogen, Methane, and Carbon Dioxide in Highly Porous Covalent Organic Frameworks for Clean Energy Applications Furukawa, Hiroyasu; Yaghi, Omar M. Journal of the American Chemical Society, Vol. 131, Issue 25, p. 8875-8883 https://doi.org/10.1021/ja9015765	journal	July 2009
Ultrahigh Porosity in Metal-Organic Frameworks Furukawa, H.; Ko, N.; Go, Y. B. Science, Vol. 329, Issue 5990, p. 424-428 https://doi.org/10.1126/science.1192160	journal	July 2010
Adsorption of Harmful Organic Vapors by Flexible Hydrophobic Bis-pyrazolate Based MOFs Galli, S.; Masciocchi, N.; Colombo, V. Chemistry of Materials, Vol. 22, Issue 5, p. 1664-1672 https://doi.org/10.1021/cm902899t	journal	March 2010
MOF-74 building unit has a direct impact on toxic gas adsorption Grant Glover, T.; Peterson, Gregory W.; Schindler, Bryan J. Chemical Engineering Science, Vol. 66, Issue 2, p. 163-170 https://doi.org/10.1016/j.ces.2010.10.002	journal	January 2011
Construction of Microporous Materials from Molecular Building Blocks Yaghi, Omar M.; Pinnavaia, Thomas J.; Thorpe, M. F. Access in Nanoporous Materials, p. 111-121 https://doi.org/10.1007/0-306-47066-7_8	book	January 2002
Construction of Porous Solids from Hydrogen-Bonded Metal Complexes of 1,3,5-Benzenetricarboxylic Acid Yaghi, O. M.; Li, Hailian; Groy, T. L. Journal of the American Chemical Society, Vol. 118, Issue 38, p. 9096-9101 https://doi.org/10.1021/ja960746q	journal	January 1996
Selective Guest Binding by Tailored Channels in a 3-D Porous Zinc(II)−Benzenetricarboxylate Network Yaghi, O. M.; Davis, Charles E.; Li, Guangming Journal of the American Chemical Society, Vol. 119, Issue 12, p. 2861-2868 https://doi.org/10.1021/ja9639473	journal	March 1997
Crystal Growth of Extended Solids by Nonaqueous Gel Diffusion Yaghi, O. M.; Li, Guangming; Li, Hailian Chemistry of Materials, Vol. 9, Issue 5, p. 1074-1076 https://doi.org/10.1021/cm970069e	journal	May 1997
A Molecular Railroad with Large Pores: Synthesis and Structure of Ni(4,4‘-bpy)_2.5(H₂O)₂(ClO₄)₂·1.5(4,4‘-bpy)·2H₂O Yaghi, O. M.; Li, Hailian; Groy, Thomas L. Inorganic Chemistry, Vol. 36, Issue 20, p. 4292-4293 https://doi.org/10.1021/ic970423a	journal	September 1997
Construction of a new open-framework solid from 1,3,5-cyclohexanetricarboxylate and zinc(II) building blocks Yaghi, Omar M.; Jernigan, Ryan; Li, Hailian Journal of the Chemical Society, Dalton Transactions, Vol. 0, Issue 14, p. 2383-2384 https://doi.org/10.1039/a702287e	journal	January 1997
Synthetic Strategies, Structure Patterns, and Emerging Properties in the Chemistry of Modular Porous Solids^† Yaghi, Omar M.; Li, Hailian; Davis, Charles Accounts of Chemical Research, Vol. 31, Issue 8, p. 474-484 https://doi.org/10.1021/ar970151f	journal	August 1998
Design of Solids from Molecular Building Blocks: Golden Opportunities for Solid State Chemistry Yaghi, O. M.; O'Keeffe, M.; Kanatzidis, M. Journal of Solid State Chemistry, Vol. 152, Issue 1, p. 1-2 https://doi.org/10.1006/jssc.2000.8733	journal	June 2000
Reticular synthesis and the design of new materials Yaghi, Omar M.; O'Keeffe, Michael; Ockwig, Nathan W. Nature, Vol. 423, Issue 6941, p. 705-714 https://doi.org/10.1038/nature01650	journal	June 2003
Metal–organic Frameworks: A tale of two entanglements Yaghi, Omar M. Nature Materials, Vol. 6, Issue 2, p. 92-93 https://doi.org/10.1038/nmat1824	journal	February 2007
Reticular Chemistry and Metal-Organic Frameworks for Clean Energy Yaghi, Omar M.; Li, Qiaowei MRS Bulletin, Vol. 34, Issue 9, p. 682-690 https://doi.org/10.1557/mrs2009.180	journal	September 2009
Docking in Metal-Organic Frameworks Li, Qiaowei; Zhang, Wenyu; Miljanic, Ognjen S. Science, Vol. 325, Issue 5942, p. 855-859 https://doi.org/10.1126/science.1175441	journal	August 2009
Thermal conductivity of a metal-organic framework (MOF-5): Part II. Measurement Huang, B. L.; Ni, Z.; Millward, A. International Journal of Heat and Mass Transfer, Vol. 50, Issue 3-4, p. 405-411 https://doi.org/10.1016/j.ijheatmasstransfer.2006.10.001	journal	February 2007
Metal-organic frameworks—New materials for hydrogen storage Isaeva, V. I.; Kustov, L. M. Russian Journal of General Chemistry, Vol. 77, Issue 4, p. 721-739 https://doi.org/10.1134/S1070363207040342	journal	April 2007
Asymmetric catalytic reactions by NbO-type chiral metal–organic frameworks Jeong, Kyung Seok; Go, Yong Bok; Shin, Sung Min Chemical Science, Vol. 2, Issue 5, p. 877-882 https://doi.org/10.1039/c0sc00582g	journal	January 2011
Impact of Preparation and Handling on the Hydrogen Storage Properties of Zn₄O(1,4-benzenedicarboxylate)₃ (MOF-5) Kaye, Steven S.; Dailly, Anne; Yaghi, Omar M. Journal of the American Chemical Society, Vol. 129, Issue 46, p. 14176-14177 https://doi.org/10.1021/ja076877g	journal	November 2007
Assembly of Metal−Organic Frameworks from Large Organic and Inorganic Secondary Building Units: New Examples and Simplifying Principles for Complex Structures Kim, Jaheon; Chen, Banglin; Reineke, Theresa M. Journal of the American Chemical Society, Vol. 123, Issue 34, p. 8239-8247 https://doi.org/10.1021/ja010825o	journal	August 2001
A Crystalline Mesoporous Coordination Copolymer with High Microporosity Koh, Kyoungmoo; Wong-Foy, Antek G.; Matzger, Adam J. Angewandte Chemie International Edition, Vol. 47, Issue 4, p. 677-680 https://doi.org/10.1002/anie.200705020	journal	January 2008
Coordinatively Unsaturated Metal Centers in the Extended Porous Framework of Zn₃(BDC)₃·6CH₃OH (BDC = 1,4-Benzenedicarboxylate) Li, Hailian; Davis, Charles E.; Groy, Thomas L. Journal of the American Chemical Society, Vol. 120, Issue 9, p. 2186-2187 https://doi.org/10.1021/ja974172g	journal	March 1998
Establishing Microporosity in Open Metal−Organic Frameworks: Gas Sorption Isotherms for Zn(BDC) (BDC = 1,4-Benzenedicarboxylate) Li, Hailian; Eddaoudi, Mohamed; Groy, Thomas L. Journal of the American Chemical Society, Vol. 120, Issue 33, p. 8571-8572 https://doi.org/10.1021/ja981669x	journal	August 1998
Design and synthesis of an exceptionally stable and highly porous metal-organic framework Li, Hailian; Eddaoudi, Mohamed; M., O'Keeffe Nature, Vol. 402, Issue 6759, p. 276-279 https://doi.org/10.1038/46248	journal	November 1999
20 Å Cd₄In₁₆S₃₅^14- Supertetrahedral T4 Clusters as Building Units in Decorated Cristobalite Frameworks Li, Hailian; Kim, Jaheon; Groy, T. L. Journal of the American Chemical Society, Vol. 123, Issue 20, p. 4867-4868 https://doi.org/10.1021/ja010413f	journal	May 2001
[Cd₁₆In₆₄S₁₃₄]^44-: 31-Å Tetrahedron with a Large Cavity Li, Hailian; Kim, Jaheon; O'Keeffe, Michael Angewandte Chemie International Edition, Vol. 42, Issue 16, p. 1819-1821 https://doi.org/10.1002/anie.200250748	journal	April 2003
A metal–organic framework replete with ordered donor–acceptor catenanes Li, Qiaowei; Zhang, Wenyu; Miljanić, Ognjen Š. Chemical Communications, Vol. 46, Issue 3, p. 380-382 https://doi.org/10.1039/B919923C	journal	January 2010
A Catenated Strut in a Catenated Metal-Organic Framework Li, Qiaowei; Sue, Chi-Hau; Basu, Subhadeep Angewandte Chemie International Edition, Vol. 49, Issue 38, p. 6751-6755 https://doi.org/10.1002/anie.201003221	journal	August 2010
The pervasive chemistry of metal–organic frameworks Long, Jeffrey R.; Yaghi, Omar M. Chemical Society Reviews, Vol. 38, Issue 5, p. 1213-1214 https://doi.org/10.1039/b903811f	journal	January 2009
Synthesis and Structure of Chemically Stable Metal−Organic Polyhedra Lu, Zheng; Knobler, Carolyn B.; Furukawa, Hiroyasu Journal of the American Chemical Society, Vol. 131, Issue 35, p. 12532-12533 https://doi.org/10.1021/ja905101s	journal	September 2009
Adsorption Mechanism and Uptake of Methane in Covalent Organic Frameworks: Theory and Experiment Mendoza-Cortés, José L.; Han, Sang Soo; Furukawa, Hiroyasu The Journal of Physical Chemistry A, Vol. 114, Issue 40, p. 10824-10833 https://doi.org/10.1021/jp1044139	journal	October 2010
Metal−Organic Frameworks with Exceptionally High Capacity for Storage of Carbon Dioxide at Room Temperature Millward, Andrew R.; Yaghi, Omar M. Journal of the American Chemical Society, Vol. 127, Issue 51, p. 17998-17999 https://doi.org/10.1021/ja0570032	journal	December 2005
Crystals as Molecules Postsynthesis Covalent Functionalization of Zeolitic Imidazolate Frameworks Morris, William; Doonan, Christian J.; Furukawa, Hiroyasu Journal of the American Chemical Society, Vol. 130, Issue 38, p. 12626-12627 https://doi.org/10.1021/ja805222x	journal	September 2008
A Combined Experimental−Computational Investigation of Carbon Dioxide Capture in a Series of Isoreticular Zeolitic Imidazolate Frameworks Morris, William; Leung, Belinda; Furukawa, Hiroyasu Journal of the American Chemical Society, Vol. 132, Issue 32, p. 11006-11008 https://doi.org/10.1021/ja104035j	journal	August 2010
Postsynthetic Modification of a Metal–Organic Framework for Stabilization of a Hemiaminal and Ammonia Uptake Morris, William; Doonan, Christian J.; Yaghi, Omar M. Inorganic Chemistry, Vol. 50, Issue 15, p. 6853-6855 https://doi.org/10.1021/ic200744y	journal	August 2011
Non-carboxylate based metal-organic frameworks (MOFs) and related aspects Natarajan, Srinivasan; Mahata, Partha Current Opinion in Solid State and Materials Science, Vol. 13, Issue 3-4, p. 46-53 https://doi.org/10.1016/j.cossms.2009.05.002	journal	June 2009
Porous Metal−Organic Truncated Octahedron Constructed from Paddle-Wheel Squares and Terthiophene Links Ni, Zheng; Yassar, Abderrahim; Antoun, Tarek Journal of the American Chemical Society, Vol. 127, Issue 37, p. 12752-12753 https://doi.org/10.1021/ja052055c	journal	September 2005
A Metal−Organic Framework with Covalently Bound Organometallic Complexes Oisaki, Kounosuke; Li, Qiaowei; Furukawa, Hiroyasu Journal of the American Chemical Society, Vol. 132, Issue 27, p. 9262-9264 https://doi.org/10.1021/ja103016y	journal	July 2010

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