Cooperative Polar Ordering of Acentric Guest Molecules in Topologically Controlled Host Frameworks
†
Current address: Department of Chemistry, Georgetown University, Box 571227, Washington, DC 20057.
*
To whom correspondence should be addressed; email: [email protected].
Cited By
This article is cited by 47 publications.
- Beau R. Brummel, Kinsey G. Lee, Colin D. McMillen, Joseph W. Kolis, Daniel C. Whitehead. One-Pot Absolute Stereochemical Identification of Alcohols via Guanidinium Sulfate Crystallization. Organic Letters 2019, 21 (23) , 9622-9627. https://doi.org/10.1021/acs.orglett.9b03792
- Leigh Loots, James P. O’Connor, Tanya le Roex, and Delia A. Haynes . Solid-State Supramolecular Chemistry of a Benzylpyridine-Functionalized Zwitterion: Polymorphism, Interconversion, and Porosity. Crystal Growth & Design 2015, 15 (12) , 5849-5857. https://doi.org/10.1021/acs.cgd.5b01238
- Chao Shi, Bin Wei, and Wen Zhang . Toward Understanding the Origin of Structural Phase Transition in Guanidinium Pyridinium 1,5-Naphthalenedisulfonate. Crystal Growth & Design 2014, 14 (12) , 6570-6580. https://doi.org/10.1021/cg5014895
- Weiwei L. Xu, Mark D. Smith, Jeanette A. Krause, Andrew B. Greytak, Shuguo Ma, Cory M. Read, and Linda S. Shimizu . Single Crystal to Single Crystal Polymerization of a Self-Assembled Diacetylene Macrocycle Affords Columnar Polydiacetylenes. Crystal Growth & Design 2014, 14 (3) , 993-1002. https://doi.org/10.1021/cg401380a
- Bharat Kumar Tripuramallu and Samar K. Das . Hydrothermal Synthesis and Structural Characterization of Metal Organophosphonate Oxide Materials: Role of Metal-Oxo Clusters in the Self Assembly of Metal Phosphonate Architectures. Crystal Growth & Design 2013, 13 (6) , 2426-2434. https://doi.org/10.1021/cg4001347
- Kinkini Roy, Arief C. Wibowo, Perry J. Pellechia, Shuguo Ma, Michael F. Geer, and Linda S. Shimizu . Absorption of Hydrogen Bond Donors by Pyridyl Bis-Urea Crystals. Chemistry of Materials 2012, 24 (24) , 4773-4781. https://doi.org/10.1021/cm302658q
- Jun He, Matthias Zeller, Allen D. Hunter, and Zhengtao Xu . White Light Emission and Second Harmonic Generation from Secondary Group Participation (SGP) in a Coordination Network. Journal of the American Chemical Society 2012, 134 (3) , 1553-1559. https://doi.org/10.1021/ja2073559
- Greg A. Hogan, Nigam P. Rath, and Alicia M. Beatty . A Stable Hydrogen-Bonded Coordination Network with Removable Guests. Crystal Growth & Design 2011, 11 (9) , 3740-3743. https://doi.org/10.1021/cg200793f
- Airon C. Soegiarto and Michael D. Ward. Directed Organization of Dye Aggregates in Hydrogen-Bonded Host Frameworks. Crystal Growth & Design 2009, 9 (8) , 3803-3815. https://doi.org/10.1021/cg900578u
- Karim Bouchmella, Sylvain G. Dutremez, Bruno Alonso, Francesco Mauri and Christel Gervais. 1H, 13C, and 15N Solid-State NMR Studies of Imidazole- and Morpholine-Based Model Compounds Possessing Halogen and Hydrogen Bonding Capabilities. Crystal Growth & Design 2008, 8 (11) , 3941-3950. https://doi.org/10.1021/cg700975v
- Kazuki Sada,, Katsunari Inoue,, Tomoyuki Tanaka,, Akira Tanaka,, Attila Epergyes,, Sadamu Nagahama,, Akikazu Matsumoto, and, Mikiji Miyata. Organic Layered Crystals with Adjustable Interlayer Distances of 1-Naphthylmethylammonium n-Alkanoates and Isomerism of Hydrogen-Bond Networks by Steric Dimension. Journal of the American Chemical Society 2004, 126 (6) , 1764-1771. https://doi.org/10.1021/ja038379n
- K. Travis Holman,, Stephen M. Martin,, Daniel P. Parker, and, Michael D. Ward. The Generality of Architectural Isomerism in Designer Inclusion Frameworks. Journal of the American Chemical Society 2001, 123 (19) , 4421-4431. https://doi.org/10.1021/ja0030257
- Zhiwen Fan, Yingbing Zou, Chulong Liu, Shengchang Xiang, Zhangjing Zhang. Hydrogen‐Bonded Organic Frameworks: Functionalized Construction Strategy by Nitrogen‐Containing Functional Group. Chemistry – A European Journal 2022, 28 (42) https://doi.org/10.1002/chem.202200422
- Beau R. Brummel, Kinsey G. Lee, Joseph W. Kolis, Daniel C. Whitehead, Colin D. McMillen. Guanidinium sulfates as directors of noncentrosymmetric structures. CrystEngComm 2021, 23 (7) , 1643-1656. https://doi.org/10.1039/D0CE01817A
- U. Gattermann, S.-H. Park, M. Kaliwoda. Synthesis and characterisation of In-doped MnWO4-type solid-solutions: Mn1−3In2□ WO4 (x=0–0.11). Journal of Solid State Chemistry 2014, 219 , 191-200. https://doi.org/10.1016/j.jssc.2014.07.039
- Matthew J. Fischer, Alicia M. Beatty. Solid phase microextraction (SPME) combined with TGA as a technique for guest analysis in crystal engineering. CrystEngComm 2014, 16 (31) , 7313-7319. https://doi.org/10.1039/C4CE00419A
- Eugene A. Mash. Crystal engineering with 1,4-piperazine-2,5-diones. CrystEngComm 2014, 16 (37) , 8620-8637. https://doi.org/10.1039/C4CE00968A
- Krapa Shankar, Babulal Das, Jubaraj B. Baruah. Cation Exchange in Layered Copper(II) Coordination Polymers. European Journal of Inorganic Chemistry 2013, 2013 (36) , 6147-6155. https://doi.org/10.1002/ejic.201300906
- Naoki Shiota, Yumeko Sakoda, Takafumi Kinuta, Yoshitane Imai. Preparation, crystal structure, and solid-state optical property of a disulfonic acid/amine fluorescent complex composed of 4,4′-biphenyldisulfonic acid and 2-naphthylethylamine. Journal of Inclusion Phenomena and Macrocyclic Chemistry 2012, 74 (1-4) , 369-374. https://doi.org/10.1007/s10847-012-0124-x
- Safa Golrokh Bahoosh, J. M. Wesselinowa. Ion doping effects in multiferroic MnWO4. Journal of Applied Physics 2012, 111 (8) https://doi.org/10.1063/1.4703913
- Madleen Busse, Philip C. Andrews, Peter C. Junk. Synthesis and Structure of Silver Amino‐Arenesulfonates. European Journal of Inorganic Chemistry 2012, 2012 (7) , 1061-1071. https://doi.org/10.1002/ejic.201101119
- Roberto Centore, Mojca Jazbinsek, Angela Tuzi, Antonio Roviello, Amedeo Capobianco, Andrea Peluso. A series of compounds forming polar crystals and showing single-crystal-to-single-crystal transitions between polar phases. CrystEngComm 2012, 14 (8) , 2645. https://doi.org/10.1039/c2ce06352b
- Graham Smith, Urs D. Wermuth. Guanidinium phenylarsonate–guanidine–water (1/1/2). Acta Crystallographica Section E Structure Reports Online 2010, 66 (8) , o1893-o1894. https://doi.org/10.1107/S1600536810025043
- Graham Smith, Urs D. Wermuth, David J. Young. Hydrate Stabilization in the Three-Dimensional Hydrogen-Bonded Structure of the Brucinium Compound, Bis(2,3-dimethoxy-10-oxostrychnidinium) Biphenyl-4,4′-disulfonate Hexahydrate. Journal of Chemical Crystallography 2010, 40 (6) , 520-525. https://doi.org/10.1007/s10870-010-9689-7
- Karim Bouchmella, Sylvain G. Dutremez, Christian Guérin, Jean-Christophe Longato, Françoise Dahan. Guanidinium Alkynesulfonates with Single-Layer Stacking Motif: Interlayer Hydrogen Bonding Between Sulfonate Anions Changes the Orientation of the Organosulfonate R Group from “Alternate Side” to “Same Side”. Chemistry - A European Journal 2010, 16 (8) , 2528-2536. https://doi.org/10.1002/chem.200901717
- Roberto Centore, Antonio Roviello. Macromolecular Systems with Second Order Nonlinear Optical Properties. 2010, 79-117. https://doi.org/10.1007/978-90-481-3192-1_2
- Graham Smith, Urs D. Wermuth, Peter C. Healy. Diammonium biphenyl-4,4′-disulfonate. Acta Crystallographica Section E Structure Reports Online 2008, 64 (1) , o47-o47. https://doi.org/10.1107/S1600536807061995
- Veneta Videnova-Adrabinska. Coordination and supramolecular network entanglements of organodisulfonates. Coordination Chemistry Reviews 2007, 251 (15-16) , 1987-2016. https://doi.org/10.1016/j.ccr.2007.03.018
- Karim Bouchmella, Bruno Boury, Sylvain G. Dutremez, Arie van der Lee. Molecular Assemblies from Imidazolyl-Containing Haloalkenes and Haloalkynes: Competition between Halogen and Hydrogen Bonding. Chemistry - A European Journal 2007, 13 (21) , 6130-6138. https://doi.org/10.1002/chem.200601508
- Zhao-Xun Lian, Jiwen Cai, Cai-Hong Chen. A series of metal-organic frameworks constructed with arenesulfonates and 4,4′-bipy ligands. Polyhedron 2007, 26 (12) , 2647-2654. https://doi.org/10.1016/j.poly.2007.01.002
- Koichi Kodama, Yuka Kobayashi, Kazuhiko Saigo. Role of the Relative Molecular Length of the Components in Ternary Inclusion Crystals in the Chiral Recognition and Assembly of Supramolecular Helical Architectures. Crystal Growth & Design 2007, 7 (5) , 935-939. https://doi.org/10.1021/cg060849c
- Veneta Videnova-Adrabinska, El?bieta Obara, Tadeusz Lis. Two-dimensional hydrogen-bonded networks in guanidinium hydrogen dicarboxylates. New Journal of Chemistry 2007, 31 (2) , 287. https://doi.org/10.1039/b614843c
- Li-Juan Chen, Xiang He, Quan-Zheng Zhang, Xiao-Yuan Wu, Can-zhong Lu. A new one-dimensional copper–molybdenum bimetallic oxide compound with coordinated 2-PBIM: [Cu(2-PBIM)MoO4] (2-PBIM=2-(2-pyridyl)benzimidazole). Inorganic Chemistry Communications 2006, 9 (7) , 740-743. https://doi.org/10.1016/j.inoche.2006.04.019
- Alicia M. Beatty, Brian A. Helfrich, Greg A. Hogan, Beth Ann Reed. Metal-Containing Dicarboxylic Acids as Building Blocks for Lamellar Inorganic−Organic Hybrid Networks. Crystal Growth & Design 2006, 6 (1) , 122-126. https://doi.org/10.1021/cg058013h
- John C. MacDonald, Mehmet V. Yigit, Kyle Mychajlonka. Two Concomitant Polymorphs of a Supramolecular Model of the Asp···His···Ser Catalytic Triad. Crystal Growth & Design 2005, 5 (6) , 2248-2255. https://doi.org/10.1021/cg050092+
- Eric Burkholder, N. Gabriel Armatas, Vladimir Golub, Charles J. O’Connor, Jon Zubieta. Synthesis, structure and magnetic properties of the one-dimensional bimetallic oxide [Cu(terpy)Mo2O7]. Journal of Solid State Chemistry 2005, 178 (10) , 3145-3151. https://doi.org/10.1016/j.jssc.2005.07.030
- Nicholas F. Stephens, Manfred Buck, Philip Lightfoot. Polar ordering of polar octahedra in [C2N2H10][VOF4(H2O)]. Journal of Materials Chemistry 2005, 15 (40) , 4298. https://doi.org/10.1039/b508959j
- Stephen Lee, Abhijit Basu Mallik, Daniel C. Fredrickson. Dipolar−Dipolar Interactions and the Crystal Packing of Nitriles, Ketones, Aldehdyes, and C( sp 2 )−F Groups. Crystal Growth & Design 2004, 4 (2) , 279-290. https://doi.org/10.1021/cg0300228
- Damian G Allis, Randy S Rarig, Eric Burkholder, Jon Zubieta. A three-dimensional bimetallic oxide constructed from octamolybdate clusters and copper–ligand cation polymer subunits. A comment on the stability of the octamolybdate isomers. Journal of Molecular Structure 2004, 688 (1-3) , 11-31. https://doi.org/10.1016/j.molstruc.2003.08.027
- C.B. Aakeröy, A.M. Beatty. Solid State, Crystal Engineering and Hydrogen Bonds. 2003, 679-688. https://doi.org/10.1016/B0-08-043748-6/01120-8
- R. Vaidhyanathan, S. Natarajan, C.N.R. Rao. Hydrogen bonded structures in organic amine oxalates. Journal of Molecular Structure 2002, 608 (2-3) , 123-133. https://doi.org/10.1016/S0022-2860(01)00944-9
- K. Travis Holman, Adam M. Pivovar, Michael D. Ward. Engineering Crystal Symmetry and Polar Order in Molecular Host Frameworks. Science 2001, 294 (5548) , 1907-1911. https://doi.org/10.1126/science.1064432
- Adam M. Pivovar, K. Travis Holman, Michael D. Ward. Shape-Selective Separation of Molecular Isomers with Tunable Hydrogen-Bonded Host Frameworks. Chemistry of Materials 2001, 13 (9) , 3018-3031. https://doi.org/10.1021/cm0104452
- A. M. Pivovar, M. D. Ward, T. Yildirim, D. A. Neumann. Vibrational mode analysis of isomorphous hydrogen-bonded guanidinium sulfonates with inelastic neutron scattering and density-functional theory. The Journal of Chemical Physics 2001, 115 (4) , 1909-1915. https://doi.org/10.1063/1.1381530
- Brian Moulton, Michael J. Zaworotko. From Molecules to Crystal Engineering: Supramolecular Isomerism and Polymorphism in Network Solids. Chemical Reviews 2001, 101 (6) , 1629-1658. https://doi.org/10.1021/cr9900432
- Ashwini Nangia. Organic nanoporous structures. Current Opinion in Solid State and Materials Science 2001, 5 (2-3) , 115-122. https://doi.org/10.1016/S1359-0286(00)00038-3
- K. Travis Holman, Adam M. Pivovar, Jennifer A. Swift, Michael D. Ward. Metric Engineering of Soft Molecular Host Frameworks. Accounts of Chemical Research 2001, 34 (2) , 107-118. https://doi.org/10.1021/ar970272f