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Structural Modularity of Unique Multicomponent Hydrogen-Bonded Organic Frameworks Based on Organosilanetriols and Silanediols as Molecular Building Blocks

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    Structural Modularity of Unique Multicomponent Hydrogen-Bonded Organic Frameworks Based on Organosilanetriols and Silanediols as Molecular Building Blocks
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    • Miriam de J. Velásquez-Hernández
      Miriam de J. Velásquez-Hernández
      Centro Conjunto de Investigación en Química Sustentable UAEM-UNAM, Carretera Toluca-Atlacomulco, km.14.5, 50200, México
      More by Miriam de J. Velásquez-Hernández
    • Aaron Torres-Huerta
      Aaron Torres-Huerta
      Centro Conjunto de Investigación en Química Sustentable UAEM-UNAM, Carretera Toluca-Atlacomulco, km.14.5, 50200, México
      More by Aaron Torres-Huerta
    • Diego Martínez-Otero
      Diego Martínez-Otero
      Centro Conjunto de Investigación en Química Sustentable UAEM-UNAM, Carretera Toluca-Atlacomulco, km.14.5, 50200, México
      More by Diego Martínez-Otero
    • Elí Sánchez-González
      Elí Sánchez-González
      Laboratorio de Fisicoquímica y Reactividad de Superficies (LaFReS), Instituto de Investigaciones en Materiales, Universidad Nacional Autónoma de México, Circuito Exterior s/n, CU, Del. Coyoacán, 04510, Ciudad de México, México
      More by Elí Sánchez-González
      Orcidhttp://orcid.org/0000-0002-5440-329X
    • Uvaldo Hernández-Balderas
      Uvaldo Hernández-Balderas
      Centro Conjunto de Investigación en Química Sustentable UAEM-UNAM, Carretera Toluca-Atlacomulco, km.14.5, 50200, México
      More by Uvaldo Hernández-Balderas
    • Ilich A. Ibarra
      Ilich A. Ibarra
      Laboratorio de Fisicoquímica y Reactividad de Superficies (LaFReS), Instituto de Investigaciones en Materiales, Universidad Nacional Autónoma de México, Circuito Exterior s/n, CU, Del. Coyoacán, 04510, Ciudad de México, México
      More by Ilich A. Ibarra
      Orcidhttp://orcid.org/0000-0002-8573-8033
    • Vojtech Jancik*
      Vojtech Jancik
      Centro Conjunto de Investigación en Química Sustentable UAEM-UNAM, Carretera Toluca-Atlacomulco, km.14.5, 50200, México
      *E-mail: [email protected]. Fax: +52 (55) 56-16-22-17.
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      Orcidhttp://orcid.org/0000-0002-1007-1764
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    Crystal Growth & Design

    Cite this: Cryst. Growth Des. 2018, 18, 7, 3805–3819
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    https://doi.org/10.1021/acs.cgd.8b00030
    Published June 4, 2018
    Copyright © 2018 American Chemical Society
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    Abstract

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    In this study we examined the use of a new class of molecular building blocks with tetrahedral nodes based on organo-bis(silanetriols) (1,4-[(HO)3SiOCEt2]2C6H4 (1) and 4,4′-[(HO)3SiOCEt2]2-(1,1′-biphenyl) (2)) and organo-bis(silanediol) (1,4-[{(HO)2(tBuO)Si}OCEt2]2C6H4 (3)) for the synthesis of multicomponent hydrogen-bonded organic frameworks (HOFs) with adjustable supramolecular patterns, and modular assembly. Thus, such reticular arrangements were readily obtained by the cocrystallization of bridged organosilanols (1, 2, and 3) with an organic diamine (1,4-diazabicyclo[2.2.2]octane (a) or trans-1,2-bis(4-pyridyl)ethylene (b)) to yield the corresponding HOFs 1a, 1b, 2a, 2b, 3a, and 3b. Single-crystal X-ray diffraction analysis revealed that the dimensionality of the network, and by consequence, its porosity, can be easily engineered by means of the modulation of the central organic backbone of the organosilanol-based tectons, as well as by the Lewis basicity and the size of the corresponding organic diamine. In this context, it was found that although 1a presents a nonporous arrangement, changing either the organic diamine as in 1b, or the spacer’s size as in 2a, it is possible to generate one-dimensional channels or zero-dimensional voids, respectively. Moreover, through gas sorption experiments, it was demonstrated that 1b exhibits structural flexibility and permanent porosity with selective adsorption of CO2 over N2.

    Copyright © 2018 American Chemical Society

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    Supporting Information

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.cgd.8b00030.

    • General experimental details for the synthesis of organo-bis(silanetriol) 4,4′-[(HO)3SiOCEt2]2-(1,1′-biphenyl) (2), thermogravimetric analyses of compounds 1, 2, and 3, PXRD patterns of HOFs 1a, 1b, 2a, 2b, 3a, and 3b, including HOF 1b before and after CO2 sorption experiments; as well as tables with selected Si–O bond lengths and O–Si–O angles (PDF)

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    CCDC 1453231 and 1815223–1815227 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif, or by emailing [email protected], or by contacting The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336033.

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    This article is cited by 8 publications.

    1. Xiyu Song, Yao Wang, Chen Wang, Dong Wang, Guowei Zhuang, Kent O. Kirlikovali, Peng Li, Omar K. Farha. Design Rules of Hydrogen-Bonded Organic Frameworks with High Chemical and Thermal Stabilities. Journal of the American Chemical Society 2022, 144 (24) , 10663-10687. https://doi.org/10.1021/jacs.2c02598
    2. Alfonso Castiñeiras, Isabel García-Santos, Josefa María González-Pérez, Antonio Bauzá, Jan K. Zaręba, Juan Niclós-Gutiérrez, Rocío Torres, Esther Vílchez, Antonio Frontera. Multicomponent Supramolecular Assemblies of Melamine and α-Hydroxycarboxylic Acids: Understanding the Hydrogen Bonding Patterns and Their Physicochemical Consequences. Crystal Growth & Design 2018, 18 (11) , 6786-6800. https://doi.org/10.1021/acs.cgd.8b01035
    3. Hina Liaquat, Muhammad Imran, Zohaib Saddique, Shoomaila Latif, Khairia Mohammed Al-Ahmary, Aamir Sohail, Hussain Raza, Mahmood Ahmed. Exploring the versatility of hydrogen-bonded organic frameworks: Advances in design, stability, and multifunctional applications. Journal of Molecular Structure 2025, 1321 , 140221. https://doi.org/10.1016/j.molstruc.2024.140221
    4. Zhenyu Ji, Qing Li, Yunzhe Zhou, Rajamani Krishna, Maochun Hong, Mingyan Wu. Synergistic C 2 H 2 Binding Sites in Hydrogen‐Bonded Supramolecular Framework for One‐Step C 2 H 4 Purification from Ternary C2 Mixture. Angewandte Chemie International Edition 2024, 63 (46) https://doi.org/10.1002/anie.202411175
    5. Zhenyu Ji, Qing Li, Yunzhe Zhou, Rajamani Krishna, Maochun Hong, Mingyan Wu. Synergistic C 2 H 2 Binding Sites in Hydrogen‐Bonded Supramolecular Framework for One‐Step C 2 H 4 Purification from Ternary C2 Mixture. Angewandte Chemie 2024, 136 (46) https://doi.org/10.1002/ange.202411175
    6. Michał Terlecki, Arkadiusz Kornowicz, Kornel Sacharczuk, Iwona Justyniak, Janusz Lewiński. Synthesis, polymorphism, and shape complementarity-induced co-crystallization of hexanuclear Co( ii ) clusters capped by a flexible heteroligand shell. Dalton Transactions 2024, 53 (16) , 7012-7022. https://doi.org/10.1039/D4DT00261J
    7. Pauline Hädinger, Alexander Hinz. Functionalized Carbazolyl Hydro‐ and Allyl‐Silanes. European Journal of Inorganic Chemistry 2022, 2022 (11) https://doi.org/10.1002/ejic.202101112
    8. Fengcai Li, Zhaojian Zheng, Guanglong Zhang, Shuwei Xia, Liangmin Yu. Multicomponent supramolecular assemblies of 1(2H)-Phthalazinone and Tetrafluoroterephthalic acid: Understanding the role of hydrogen bonding on the structure and properties using experimental and computational analyses. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 2020, 228 , 117689. https://doi.org/10.1016/j.saa.2019.117689
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    Crystal Growth & Design

    Cite this: Cryst. Growth Des. 2018, 18, 7, 3805–3819
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.cgd.8b00030
    Published June 4, 2018
    Copyright © 2018 American Chemical Society
    Request reuse permissions

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