ACS Publications. Most Trusted. Most Cited. Most Read
My Activity
CONTENT TYPES
RETURN TO ISSUECommunicationNEXT

Cooperative Polar Ordering of Acentric Guest Molecules in Topologically Controlled Host Frameworks

View Author Information
Department of Chemical Engineering and Materials Science, University of Minnesota, 421 Washington Avenue, SE, Minneapolis, Minnesota 55455
Cite this: Chem. Mater. 2000, 12, 6, 1501–1504
Publication Date (Web):June 2, 2000
https://doi.org/10.1021/cm000026p
Copyright © 2000 American Chemical Society

    Article Views

    554

    Altmetric

    -

    Citations

    LEARN ABOUT THESE METRICS
    Read OnlinePDF (521 KB)
    Supporting Info (1)»

     Current address:  Department of Chemistry, Georgetown University, Box 571227, Washington, DC 20057.

    *

     To whom correspondence should be addressed; email:  [email protected].

    Supporting Information Available

    ARTICLE SECTIONS
    Jump To

    Tables of atomic coordinates and thermal parameters for compounds IIV (also to be deposited in the Cambridge Crystallographic Database) and the calculations of the dipole−dipole energies of motifs A−D. This material is available free of charge via the Internet at http://pubs.acs.org.

    Terms & Conditions

    Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system: http://pubs.acs.org/page/copyright/permissions.html.

    Cited By

    This article is cited by 47 publications.

    1. 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
    2. 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
    3. 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
    4. 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
    5. 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
    6. 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
    7. 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
    8. 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
    9. 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
    10. 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
    11. 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
    12. 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
    13. 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
    14. 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
    15. 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
    16. 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
    17. Eugene A. Mash. Crystal engineering with 1,4-piperazine-2,5-diones. CrystEngComm 2014, 16 (37) , 8620-8637. https://doi.org/10.1039/C4CE00968A
    18. 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
    19. 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
    20. 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
    21. 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
    22. 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
    23. 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
    24. 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
    25. 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
    26. 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
    27. 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
    28. 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
    29. 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
    30. 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
    31. 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
    32. 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
    33. 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
    34. 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
    35. 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+
    36. 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
    37. 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
    38. 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
    39. 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
    40. 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
    41. 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
    42. 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
    43. 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
    44. 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
    45. 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
    46. 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
    47. 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

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    You’ve supercharged your research process with ACS and Mendeley!

    STEP 1:
    Click to create an ACS ID

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    MENDELEY PAIRING EXPIRED
    Your Mendeley pairing has expired. Please reconnect