Diffusion of vaporous guests into a seemingly non-porous organic crystal

Herbert, Simon A.; Janiak, Agnieszka; Thallapally, Praveen K.; Atwood, Jerry L.; Barbour, Leonard J.

doi:10.1039/c4cc07366e

Diffusion of vaporous guests into a seemingly non-porous organic crystal

Journal Article · Tue Oct 07 00:00:00 EDT 2014 · ChemComm

DOI:https://doi.org/10.1039/c4cc07366e· OSTI ID:1166838

Herbert, Simon A. ^[1]; Janiak, Agnieszka ^[1]; Thallapally, Praveen K. ^[2]; Atwood, Jerry L. ^[3]; Barbour, Leonard J. ^[1]

Univ. of Stellenbosch, Matieland (South Africa)
Pacific Northwest National Lab. (PNNL), Richland, WA (United States)
Univ. of Missouri-Columbia, Columbia, MO (United States)

In this research, the tetragonal apohost phase of p-tert-butyltetramethoxythiacalix[4]arene absorbs hydrochloric acid and iodine. These guest molecules occupy different sites in the solid-state structure -- either within the small intrinsic voids of the macrocycle or within the interstitial spaces between the host molecules. This study illustrates the dynamic deformation of the host, providing strong mechanistic insight into the diffusion of guests into this seemingly non-porous material.

View Accepted Manuscript (DOE)

Research Organization:: Pacific Northwest National Laboratory (PNNL), Richland, WA (United States)

Sponsoring Organization:: USDOE

Grant/Contract Number:: AC05-76RL01830

OSTI ID:: 1166838

Report Number(s):: PNNL-SA--101277; KC0203020

Journal Information:: ChemComm, Journal Name: ChemComm Journal Issue: 98 Vol. 50; ISSN CHCOFS; ISSN 1359-7345

Publisher:: Royal Society of ChemistryCopyright Statement

Country of Publication:: United States

Language:: English

References (35)

Diffusion of Water in a Nonporous Hydrophobic Crystal Thallapally, Praveen K.; Lloyd, Gareth O.; Atwood, Jerry L. Angewandte Chemie, Vol. 117, Issue 25 https://doi.org/10.1002/ange.200500749	journal	June 2005
Solid-State Interconversions of Coordination Networks and Hydrogen-Bonded Salts Adams, Christopher J.; Colquhoun, Howard M.; Crawford, Paul C. Angewandte Chemie, Vol. 119, Issue 7 https://doi.org/10.1002/ange.200603593	journal	February 2007
Mechanistic Insights into a Gas-Solid Reaction in Molecular Crystals: The Role of Hydrogen Bonding Mínguez Espallargas, Guillermo; van de Streek, Jacco; Fernandes, Philippe Angewandte Chemie, Vol. 122, Issue 47 https://doi.org/10.1002/ange.201003265	journal	October 2010
Large Self-Assembled Chiral Organic Cages: Synthesis, Structure, and Shape Persistence Jelfs, Kim E.; Wu, Xiaofeng; Schmidtmann, Marc Angewandte Chemie, Vol. 123, Issue 45 https://doi.org/10.1002/ange.201105104	journal	September 2011
Diffusion of Water in a Nonporous Hydrophobic Crystal Thallapally, Praveen K.; Lloyd, Gareth O.; Atwood, Jerry L. Angewandte Chemie International Edition, Vol. 44, Issue 25 https://doi.org/10.1002/anie.200500749	journal	June 2005
Solid-State Interconversions of Coordination Networks and Hydrogen-Bonded Salts Adams, Christopher J.; Colquhoun, Howard M.; Crawford, Paul C. Angewandte Chemie International Edition, Vol. 46, Issue 7 https://doi.org/10.1002/anie.200603593	journal	February 2007
Mechanistic Insights into a Gas-Solid Reaction in Molecular Crystals: The Role of Hydrogen Bonding Mínguez Espallargas, Guillermo; van de Streek, Jacco; Fernandes, Philippe Angewandte Chemie International Edition, Vol. 49, Issue 47 https://doi.org/10.1002/anie.201003265	journal	October 2010
Large Self-Assembled Chiral Organic Cages: Synthesis, Structure, and Shape Persistence Jelfs, Kim E.; Wu, Xiaofeng; Schmidtmann, Marc Angewandte Chemie International Edition, Vol. 50, Issue 45 https://doi.org/10.1002/anie.201105104	journal	September 2011
Molecular Organic Crystals: From Barely Porous to Really Porous Cooper, Andrew I. Angewandte Chemie International Edition, Vol. 51, Issue 32 https://doi.org/10.1002/anie.201203117	journal	June 2012
Engineering Void Space in Organic van der Waals Crystals: Calixarenes Lead the Way Dalgarno, Scott J.; Thallapally, Praveen K.; Barbour, Leonard J. ChemInform, Vol. 38, Issue 17 https://doi.org/10.1002/chin.200717263	journal	April 2007
Metal−Organic Frameworks with Functional Pores for Recognition of Small Molecules Chen, Banglin; Xiang, Shengchang; Qian, Guodong Accounts of Chemical Research, Vol. 43, Issue 8 https://doi.org/10.1021/ar100023y	journal	August 2010
Thermally Programmable Gas Storage and Release in Single Crystals of an Organic van der Waals Host Enright, Gary D.; Udachin, Konstantin A.; Moudrakovski, Igor L. Journal of the American Chemical Society, Vol. 125, Issue 33 https://doi.org/10.1021/ja0351701	journal	August 2003
Frustrated Organic Solids Display Unexpected Gas Sorption Thallapally, Praveen K.; Dalgarno, Scott J.; Atwood, Jerry L. Journal of the American Chemical Society, Vol. 128, Issue 47 https://doi.org/10.1021/ja065499x	journal	November 2006
Reversible Gas Uptake by a Nonporous Crystalline Solid Involving Multiple Changes in Covalent Bonding Mínguez Espallargas, Guillermo; Hippler, Michael; Florence, Alastair J. Journal of the American Chemical Society, Vol. 129, Issue 50 https://doi.org/10.1021/ja075265t	journal	December 2007
Supramolecular Engineering of Intrinsic and Extrinsic Porosity in Covalent Organic Cages Bojdys, Michael J.; Briggs, Michael E.; Jones, James T. A. Journal of the American Chemical Society, Vol. 133, Issue 41 https://doi.org/10.1021/ja2056374	journal	October 2011
Metal–Organic Framework Materials with Ultrahigh Surface Areas: Is the Sky the Limit? Farha, Omar K.; Eryazici, Ibrahim; Jeong, Nak Cheon Journal of the American Chemical Society, Vol. 134, Issue 36, p. 15016-15021 https://doi.org/10.1021/ja3055639	journal	August 2012
Electrooptical Properties and Molecular Polarization of Iodine, I ₂ Maroulis, George; Makris, Constantinos; Hohm, Uwe The Journal of Physical Chemistry A, Vol. 101, Issue 5 https://doi.org/10.1021/jp962578u	journal	January 1997
Ordered porous materials for emerging applications Davis, Mark E. Nature, Vol. 417, Issue 6891, p. 813-821 https://doi.org/10.1038/nature00785	journal	June 2002
Ligand exchanges and selective catalytic hydrogenation in molecular single crystals Huang, Zheng; White, Peter S.; Brookhart, Maurice Nature, Vol. 465, Issue 7298 https://doi.org/10.1038/nature09085	journal	June 2010
Porous organic cages Tozawa, Tomokazu; Jones, James T. A.; Swamy, Shashikala I. Nature Materials, Vol. 8, Issue 12, p. 973-978 https://doi.org/10.1038/nmat2545	journal	October 2009
Supramolecular gas–solid reaction between formic acid vapours and solid [Co ^III (η ⁵ -C ₅ H ₄ COOH)(η ⁵ -C ₅ H ₄ COO)] Braga, Dario; Maini, Lucia; Mazzotti, Michele Chem. Commun., Issue 20 https://doi.org/10.1039/B207581D	journal	January 2002
Mechanistic studies of heterophase protonation and deprotonation reactions of solid [Co ^III (η ⁵ –C ₅ H ₄ COOH)(η ⁵ –C ₅ H ₄ COO)] using supermicroscopy Kaupp, Gerd; Naimi-Jamal, M. Reza; Maini, Lucia CrystEngComm, Vol. 5, Issue 84 https://doi.org/10.1039/B312293J	journal	January 2003
Synthesis and polymorphism of (4-ClpyH) ₂ [CuCl ₄ ]: solid–gas and solid–solid reactions Vitorica-Yrezabal, Iñigo J.; Sullivan, Rachel A.; Purver, Stephen L. CrystEngComm, Vol. 13, Issue 9 https://doi.org/10.1039/C0CE00628A	journal	January 2011
Covalent organic frameworks (COFs): from design to applications Ding, San-Yuan; Wang, Wei Chem. Soc. Rev., Vol. 42, Issue 2 https://doi.org/10.1039/C2CS35072F	journal	January 2013
Reversible trapping of acid and base vapours into an amphoteric crystalline material Braga, Dario; Cojazzi, Gianna; Emiliani, Dario Chemical Communications, Issue 21, p. 2272-2273 https://doi.org/10.1039/b106984e	journal	October 2001
Crystal porosity and the burden of proof Barbour, Leonard J. Chemical Communications, Issue 11 https://doi.org/10.1039/b515612m	journal	January 2006
Selective guest inclusion in a non-porous H-bonded host Dalrymple, Sean A.; Shimizu, George K. H. Chemical Communications, Issue 9 https://doi.org/10.1039/b515735h	journal	January 2006
Engineering void space in organic van der Waals crystals: calixarenes lead the way Dalgarno, Scott J.; Thallapally, Praveen K.; Barbour, Leonard J. Chemical Society Reviews, Vol. 36, Issue 2 https://doi.org/10.1039/b606047c	journal	January 2007
Selective gas adsorption and separation in metal–organic frameworks Li, Jian-Rong; Kuppler, Ryan J.; Zhou, Hong-Cai Chemical Society Reviews, Vol. 38, Issue 5, p. 1477-1504 https://doi.org/10.1039/b802426j	journal	January 2009
Nanoporous molecular crystals McKeown, Neil B. Journal of Materials Chemistry, Vol. 20, Issue 47 https://doi.org/10.1039/c0jm01867h	journal	January 2010
Different structural destinations: comparing reactions of [CuBr2(3-Brpy)2] crystals with HBr and HCl gas Mínguez Espallargas, Guillermo; Florence, Alastair J.; van de Streek, Jacco CrystEngComm, Vol. 13, Issue 13 https://doi.org/10.1039/c1ce05222e	journal	January 2011
Porous organic molecular materials Tian, Jian; Thallapally, Praveen K.; McGrail, B. Peter CrystEngComm, Vol. 14, Issue 6 https://doi.org/10.1039/c2ce06457j	journal	January 2012
The Cambridge Structural Database: a quarter of a million crystal structures and rising Allen, Frank H. Acta Crystallographica Section B Structural Science, Vol. 58, Issue 3 https://doi.org/10.1107/S0108768102003890	journal	May 2002
Guest Transport in a Nonporous Organic Solid via Dynamic van der Waals Cooperativity Atwood, J. L.; Barbour, L. J.; Jerga, A. Science, Vol. 298, Issue 5595 https://doi.org/10.1126/science.1077591	journal	November 2002
Nonporous Organic Solids Capable of Dynamically Resolving Mixtures of Diiodoperfluoroalkanes Metrangolo, P.; Carcenac, Y.; Lahtinen, M. Science, Vol. 323, Issue 5920 https://doi.org/10.1126/science.1168679	journal	March 2009

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Guest-Induced Breathing Effect in a Flexible Molecular Crystal Sheng, Yujie; Chen, Qibin; Yao, Junyao Angewandte Chemie International Edition, Vol. 55, Issue 10 https://doi.org/10.1002/anie.201510637	journal	February 2016
High-temperature in situ crystallographic observation of reversible gas sorption in impermeable organic cages Baek, Seung Bin; Moon, Dohyun; Graf, Robert Proceedings of the National Academy of Sciences, Vol. 112, Issue 46 https://doi.org/10.1073/pnas.1504586112	journal	November 2015
An unexpected relationship between solvent inclusion and gas sorption properties of chiral calixsalen solids Janiak, Agnieszka; Kwit, Marcin; Barbour, Leonard J. Supramolecular Chemistry, Vol. 30, Issue 5-6 https://doi.org/10.1080/10610278.2018.1427865	journal	January 2018
An unexpected relationship between solvent inclusion and gas sorption properties of chiral calixsalen solids^* Janiak, Agnieszka; Kwit, Marcin; Barbour, Leonard J. Taylor & Francis https://doi.org/10.6084/m9.figshare.5809500	text	January 2018

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CCDC 973280: Experimental Crystal Structure Determination: ROPQIY : 5,11,17,23-Tetra-t-butyl-25,26,27,28-tetramethoxycalix(4)arene hydrogen chloride Herbert, Simon A.; Janiak, Agnieszka; Thallapally, Praveen K. https://doi.org/10.5517/cc11ns4m The current record is supplemented by this dataset	dataset	November 2013
CCDC 973281: Experimental Crystal Structure Determination: ROPQOE : 5,11,17,23-Tetra-t-butyl-25,26,27,28-tetramethoxycalix(4)arene hydrogen chloride hydrate Herbert, Simon; Janiak, Agnieszka; Thallapally, Praveen https://doi.org/10.5517/cc11ns5n The current record is supplemented by this dataset	dataset	November 2013
CCDC 973282: Experimental Crystal Structure Determination: ROPQUK : p-t-butylthiacalix[4]arene diiodide Space Group: P 4 21 m (113), Cell: a 19.544(3)Å b 19.544(3)Å c 11.924(2)Å, α 90.00° β 90.00° γ 90.00° Herbert, Simon A.; Janiak, Agnieszka; Thallapally, Praveen K. https://doi.org/10.5517/cc11ns6p The current record is supplemented by this dataset	dataset	November 2013
CCDC 973283: Experimental Crystal Structure Determination: ROPRAR : p-t-butylthiacalix[4]arene diiodide hemihydrate Space Group: P 4 21 m (113), Cell: a 19.523(2)Å b 19.523(2)Å c 11.9511(12)Å, α 90.00° β 90.00° γ 90.00° Herbert, Simon A.; Janiak, Agnieszka; Thallapally, Praveen K. https://doi.org/10.5517/cc11ns7q The current record is supplemented by this dataset	dataset	November 2013

Diffusion of vaporous guests into a seemingly non-porous organic crystal

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