ACS Publications. Most Trusted. Most Cited. Most Read
Molecular Recognition of Organic Vapors by Adamantylcalix[4]arene in QCM Sensor Using Partial Binding Reversibility

OR SEARCH CITATIONS

My Activity
Publications

Figure 1Loading Img
Download Hi-Res ImageDownload to MS-PowerPointCite This:J. Phys. Chem. B 2008, 112, 49, 15569-15575
    Article

    Molecular Recognition of Organic Vapors by Adamantylcalix[4]arene in QCM Sensor Using Partial Binding Reversibility
    Click to copy article linkArticle link copied!

    View Author Information
    Institute of Chemistry, Kazan State University, Kremlevskaya 18, Kazan 420008, Russia; Department of Chemistry, Virginia Commonwealth University, Richmond, Virginia 23284; and Department of Chemistry, Moscow State University, Moscow 119992, Russia
    * Corresponding author: e-mail [email protected]; Ph +7-843-2315309; Fax +7-843-2927418.
    †Kazan State University.
    ‡Virginia Commonwealth University.
    §Moscow State University.
    Other Access OptionsSupporting Information (1)

    The Journal of Physical Chemistry B

    Cite this: J. Phys. Chem. B 2008, 112, 49, 15569–15575
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jp804277u
    Published November 14, 2008
    Copyright © 2008 American Chemical Society
    Request reuse permissions

    Abstract

    Click to copy section linkSection link copied!

    The parameters of stability, guest binding reversibility, and Gibbs energy of guest inclusion were determined for clathrates of adamantylcalix[4]arene (1). These data provide a new insight into the structure−property relationships in vapor sensor applications of clathrate-forming hosts. A thin layer of 1, used in the quartz microbalance (QCM) sensor, demonstrates a selectivity for organic vapors, which depends on the regeneration technique after the guest binding. Complete regeneration of 1 on the sensor surface was reached through the exchange of bound guest with ethanol vapor, which forms an unstable clathrate with 1. The efficiency of the used regeneration technique was proved by comparing the QCM data with the isotherms of guest vapor sorption by guest-free host 1 and with the data of simultaneous thermogravimetry and differential scanning calorimetry for the saturated clathrates of 1. In sensor, the extent of host regeneration without guest exchange depends on the guest molecular structure. This extent, or guest-binding reversibility parameter, being determined in a combination with the sensor responses of completely regenerated 1 to guest vapors, increases the recognition capability of single sensor device. Using this technique, 13 of 15 studied guests were discriminated. The structural hints on the suitable sensor properties of 1 were found in the determined X-ray monocrystal data for clathrate of this host with toluene.

    Copyright © 2008 American Chemical Society

    Subjects

    what are subjects

    Read this article

    To access this article, please review the available access options below.

    Get instant access

    Purchase Access

    Read this article for 48 hours. Check out below using your ACS ID or as a guest.

    Recommended

    Access through Your Institution

    You may have access to this article through your institution.

    Your institution does not have access to this content. Add or change your institution or let them know you’d like them to include access.

    Supporting Information

    Click to copy section linkSection link copied!

    Powder X-ray diffraction data, data of simultaneous thermogravimetry and differential scanning calorimetry for adamantylcalix[4]arene and its clathrates, QCM data for guest exchange in toluene clathrate of adamantylcalix[4]arene, data of thermogravimetry with mass spectrometric analysis of released vapors for product of guest exchange in this clathrate, and vapor sorption isotherms of guests by α-phase of adamantylcalix[4]arene. This material is available free of charge via the Internet at http://pubs.acs.org.

    Terms & Conditions

    Electronic Supporting Information files are available without a subscription to ACS Web Editions. The American Chemical Society holds a copyright ownership interest in any copyrightable Supporting Information. Files available from the ACS website may be downloaded for personal use only. Users are not otherwise permitted to reproduce, republish, redistribute, or sell any Supporting Information from the ACS website, either in whole or in part, in either machine-readable form or any other form without permission from the American Chemical Society. For permission to reproduce, republish and redistribute this material, requesters must process their own requests via the RightsLink permission system. Information about how to use the RightsLink permission system can be found at http://pubs.acs.org/page/copyright/permissions.html.

    Cited By

    Click to copy section linkSection link copied!

    This article is cited by 44 publications.

    1. Marat A. Ziganshin, Aisylu S. Safiullina, Alexander V. Gerasimov, Sufia A. Ziganshina, Alexander E. Klimovitskii, Khasan R. Khayarov, and Valery V. Gorbatchuk . Thermally Induced Self-Assembly and Cyclization of l-Leucyl-l-Leucine in Solid State. The Journal of Physical Chemistry B 2017, 121 (36) , 8603-8610. https://doi.org/10.1021/acs.jpcb.7b06759
    2. Karina V. Gataullina, Marat A. Ziganshin, Ivan I. Stoikov, Alexander E. Klimovitskii, Aidar T. Gubaidullin, Kinga Suwińska, and Valery V. Gorbatchuk . Smart Polymorphism of Thiacalix[4]arene with Long-Chain Amide Containing Substituents. Crystal Growth & Design 2017, 17 (6) , 3512-3527. https://doi.org/10.1021/acs.cgd.7b00463
    3. Valery V. Gorbatchuk, Askar K. Gatiatulin, Marat A. Ziganshin, Aidar T. Gubaidullin, and Luidmila S. Yakimova . Unusually High Efficiency of β-Cyclodextrin Clathrate Preparation by Water-Free Solid-Phase Guest Exchange. The Journal of Physical Chemistry B 2013, 117 (46) , 14544-14556. https://doi.org/10.1021/jp408059b
    4. Shamil F. Galyaltdinov, Marat A. Ziganshin, Andriy B. Drapailo, and Valery V. Gorbatchuk . Unusually High Selectivity of Guest Exchange in tert-Butylthiacalix[4]arene Clathrate Producing More Thermostable Inclusion and Memory of Guest. The Journal of Physical Chemistry B 2012, 116 (36) , 11379-11385. https://doi.org/10.1021/jp3065739
    5. Radislav A. Potyrailo, Cheryl Surman, Nandini Nagraj, and Andrew Burns . Materials and Transducers Toward Selective Wireless Gas Sensing. Chemical Reviews 2011, 111 (11) , 7315-7354. https://doi.org/10.1021/cr2000477
    6. Adrien Bourennane, Camel Tanougast, Camille Diou, Jean Gorse. Accurate Multi-Channel QCM Sensor Measurement Enabled by FPGA-Based Embedded System Using GPS. Electronics 2023, 12 (12) , 2666. https://doi.org/10.3390/electronics12122666
    7. Askar K. Gatiatulin, Viktoria Yu. Osel’skaya, Marat A. Ziganshin, Valery V. Gorbatchuk. Guest exchange in anhydrous inclusion compounds of α-cyclodextrin and its amorphization. Journal of Thermal Analysis and Calorimetry 2021, 146 (6) , 2417-2422. https://doi.org/10.1007/s10973-020-10428-0
    8. Igor S. Antipin, Mikhail V. Alfimov, Vladimir V. Arslanov, Vladimir A. Burilov, Sergey Z. Vatsadze, Yan Z. Voloshin, Konstantin P. Volcho, Valery V. Gorbatchuk, Yulia G. Gorbunova, Sergey P. Gromov, Semyon V. Dudkin, Sergei Yu. Zaitsev, Lucia Ya. Zakharova, Marat A. Ziganshin, Anna V. Zolotukhina, Maria A. Kalinina, Eduard A. Karakhanov, Ruslan R. Kashapov, Oskar I. Koifman, Alexander I. Konovalov, Vladimir S. Korenev, Anton L. Maksimov, Nugzar Zh. Mamardashvili, Galina M. Mamardashvili, Alexander G. Martynov, Asiya R. Mustafina, Ramil I. Nugmanov, Alexander S. Ovsyannikov, Pavel L. Padnya, Andrei S. Potapov, Sofiya L. Selektor, Maxim N. Sokolov, Svetlana E. Solovieva, Ivan I. Stoikov, Pavel A. Stuzhin, Evgenii V. Suslov, Evgeny N. Ushakov, Vladimir P. Fedin, Svetlana V. Fedorenko, Olga A. Fedorova, Yury V. Fedorov, Sergei N. Chvalun, Aslan Yu. Tsivadze, Sergei N. Shtykov, Dmitriy N. Shurpik, Maxim A. Shcherbina, Luidmila S. Yakimova. Functional supramolecular systems: design and applications. Russian Chemical Reviews 2021, 90 (8) , 895-1107. https://doi.org/10.1070/RCR5011
    9. Ilya A. Perov, Sufia A. Ziganshina, Radik A. Larionov, Alexander V. Gerasimov, Valery V. Gorbatchuk, Marat A. Ziganshin. Smart thermal behavior of tripeptide leucyl-leucyl-leucine towards vapors of binary mixture of benzene and tetrachloromethane. Thermochimica Acta 2021, 700 , 178937. https://doi.org/10.1016/j.tca.2021.178937
    10. Mukhammet N. Gabdulkhaev, Marat A. Ziganshin, Aleksey V. Buzyurov, Christoph Schick, Svetlana E. Solovieva, Elena V. Popova, Aidar T. Gubaidullin, Valery V. Gorbatchuk. Smart control of calixarene polymorphic states. CrystEngComm 2020, 22 (42) , 7002-7015. https://doi.org/10.1039/D0CE01070G
    11. Luidmila S. Yakimova, Aigul R. Nugmanova, Olga A. Mostovaya, Alena A. Vavilova, Dmitriy N. Shurpik, Timur A. Mukhametzyanov, Ivan I. Stoikov. Nanostructured Polyelectrolyte Complexes Based on Water-Soluble Thiacalix[4]Arene and Pillar[5]Arene: Self-Assembly in Micelleplexes and Polyplexes at Packaging DNA. Nanomaterials 2020, 10 (4) , 777. https://doi.org/10.3390/nano10040777
    12. Askar K. Gatiatulin, Marat A. Ziganshin, Valery V. Gorbatchuk. Smart Molecular Recognition: From Key-to-Lock Principle to Memory-Based Selectivity. Frontiers in Chemistry 2020, 7 https://doi.org/10.3389/fchem.2019.00933
    13. Askar K. Gatiatulin, Viktoria Yu. Osel'skaya, Marat A. Ziganshin, Valery V. Gorbatchuk. Smart control of guest inclusion by α-cyclodextrin using its hydration history. RSC Advances 2019, 9 (65) , 37778-37787. https://doi.org/10.1039/C9RA08710A
    14. Luidmila Yakimova, Pavel Padnya, Daria Tereshina, Aisylu Kunafina, Aigul Nugmanova, Yuri Osin, Vladimir Evtugyn, Ivan Stoikov. Interpolyelectrolyte mixed nanoparticles from anionic and cationic thiacalix[4]arenes for selective recognition of model biopolymers. Journal of Molecular Liquids 2019, 279 , 9-17. https://doi.org/10.1016/j.molliq.2019.01.099
    15. Karina V. Gataullina, Aleksey V. Buzyurov, Marat A. Ziganshin, Pavel L. Padnya, Ivan I. Stoikov, Christoph Schick, Valery V. Gorbatchuk. Using fast scanning calorimetry to detect guest-induced polymorphism by irreversible phase transitions in the nanogram scale. CrystEngComm 2019, 21 (6) , 1034-1041. https://doi.org/10.1039/C8CE01865K
    16. Askar K. Gatiatulin, Viktoria Yu. Osel'skaya, Marat A. Ziganshin, Valery V. Gorbatchuk. Size exclusion effect in binary inclusion compounds of α-cyclodextrin. Physical Chemistry Chemical Physics 2018, 20 (41) , 26105-26116. https://doi.org/10.1039/C8CP03104E
    17. Csaba Németh, Dóra Szabó, Benjámin Gyarmati, Alexander Gerasimov, Mikhail Varfolomeev, Timur Abdullin, Krisztina László, András Szilágyi. Effect of side groups on the properties of cationic polyaspartamides. European Polymer Journal 2017, 93 , 805-814. https://doi.org/10.1016/j.eurpolymj.2017.02.024
    18. V.V. Gorbatchuk, A.K. Gatiatulin, M.A. Ziganshin. Gas/Solid Complexation and Inclusion. 2017, 139-150. https://doi.org/10.1016/B978-0-12-409547-2.12499-0
    19. Marat A. Ziganshin, Aisylu S. Safiullina, Sufia A. Ziganshina, Alexander V. Gerasimov, Valery V. Gorbatchuk. Non-zeolitic properties of the dipeptide l -leucyl– l -leucine as a result of the specific nanostructure formation. Physical Chemistry Chemical Physics 2017, 19 (21) , 13788-13797. https://doi.org/10.1039/C7CP01393K
    20. Mukhammet N. Gabdulkhaev, Askar K. Gatiatulin, Marat A. Ziganshin, Valery V. Gorbatchuk. Nonlinear effect of two remembered guests in their mixtures on the host memory for guest inclusion and release. Journal of Thermal Analysis and Calorimetry 2016, 126 (2) , 627-632. https://doi.org/10.1007/s10973-016-5558-8
    21. R. R. Zairov, N. А. Shamsutdinova, А. N. Fattakhova, А. V. Pyataev, А. F. Abdullin, А. V. Gerasimov, А. Т. Gubaidullin, А. R. Mustafina. Nanoparticles based on gadolinium(iii) and europium(iii) complexes for biovisualization. Russian Chemical Bulletin 2016, 65 (5) , 1325-1331. https://doi.org/10.1007/s11172-016-1456-2
    22. Ivan I. Stoikov, Luidmila S. Yakimova, Joshua B. Puplampu, Alena A. Vavilova. Systems Based on Calixarenes as the Basis for the Creation of Catalysts and Nanocontainers. 2016, 85-110. https://doi.org/10.1016/B978-0-12-801713-5.00004-5
    23. L. S. Yakimova, D. N. Shurpik, I. I. Stoikov. Amide-functionalized pillar[5]arenes as a novel class of macrocyclic receptors for the sensing of H 2 PO 4 − anion. Chemical Communications 2016, 52 (84) , 12462-12465. https://doi.org/10.1039/C6CC05797G
    24. L. S. Yakimova, D. N. Shurpik, L. H. Gilmanova, A. R. Makhmutova, A. Rakhimbekova, I. I. Stoikov. Highly selective binding of methyl orange dye by cationic water-soluble pillar[5]arenes. Organic & Biomolecular Chemistry 2016, 14 (18) , 4233-4238. https://doi.org/10.1039/C6OB00539J
    25. Askar K. Gatiatulin, Marat A. Ziganshin, Goulshat F. Yumaeva, Aidar T. Gubaidullin, Kinga Suwińska, Valery V. Gorbatchuk. Using water-mimic organic compounds to activate guest inclusion by initially dry beta-cyclodextrin. RSC Advances 2016, 6 (66) , 61984-61995. https://doi.org/10.1039/C6RA11378H
    26. M. A. Ziganshin, N. S. Gubina, V. V. Gorbatchuk, S. A. Ziganshina, A. P. Chuklanov, D. A. Bizyaev, A. A. Bukharaev. AFM study of thin films of oligopeptide L-valyl-L-valine before and after interaction with vapors. Journal of Surface Investigation. X-ray, Synchrotron and Neutron Techniques 2016, 10 (1) , 210-216. https://doi.org/10.1134/S1027451016010377
    27. M. A. Varfolomeev, A. N. Grachev, A. A. Makarov, S. A. Zabelkin, V. N. Emel’yanenko, T. R. Musin, A. V. Gerasimov, D. K. Nurgaliev. Thermal Analysis and Calorimetric Study of the Combustion of Hydrolytic Wood Lignin and Products of Its Pyrolysis. Chemistry and Technology of Fuels and Oils 2015, 51 (1) , 140-145. https://doi.org/10.1007/s10553-015-0586-9
    28. Marat A. Ziganshin, Alexander V. Gerasimov, Valery V. Gorbatchuk, Aidar T. Gubaidullin. Thermal analysis of clathrates of tripeptide LLL with organic compounds and water. Journal of Thermal Analysis and Calorimetry 2015, 119 (3) , 1811-1816. https://doi.org/10.1007/s10973-014-4279-0
    29. Marat A. Ziganshin, Nadezhda S. Gubina, Alexander V. Gerasimov, Valery V. Gorbatchuk, Sufia A. Ziganshina, Anton P. Chuklanov, Anastas A. Bukharaev. Interaction of l -alanyl- l -valine and l -valyl- l -alanine with organic vapors: thermal stability of clathrates, sorption capacity and the change in the morphology of dipeptide films. Physical Chemistry Chemical Physics 2015, 17 (31) , 20168-20177. https://doi.org/10.1039/C5CP03309H
    30. Askar K. Gatiatulin, Marat A. Ziganshin, Valery V. Gorbatchuk. Selective preparation of beta-cyclodextrin clathrates by solid-phase exchange of included tetrahydrofurane for volatile guests in absence of water. Journal of Thermal Analysis and Calorimetry 2014, 118 (2) , 987-992. https://doi.org/10.1007/s10973-014-3800-9
    31. M. A. Ziganshin, V. V. Gorbatchuk, R. R. Sitdikov, I. I. Stoikov, I. S. Antipin. Molecular recognition of organic compounds by the data on polymorphic and pseudo-polymorphic transformations of tert-butylthiacalix[4]arene derivative. Russian Chemical Bulletin 2014, 63 (1) , 201-206. https://doi.org/10.1007/s11172-014-0414-0
    32. Tobias Gruber, Frank Eißmann, Margit Gruner, Luisa G. Heinz, Wilhelm Seichter, Edwin Weber. Simple dinitro substituted calix[4]arene forming a honeycomb-like architecture with hydrophobic channels. CrystEngComm 2014, 16 (18) , 3730-3736. https://doi.org/10.1039/C3CE41819G
    33. S. F. Galyaltdinov, M. A. Ziganshin, A. T. Gubaidullin, S. G. Vyshnevsky, O. I. Kalchenko, V. V. Gorbatchuk. Anti-sieve effect in guest inclusion by thiacalix[4]arene giving a surge in thermal stability of its clathrates prepared by solid-phase guest exchange. CrystEngComm 2014, 16 (18) , 3781-3787. https://doi.org/10.1039/C3CE42304B
    34. M. A. Ziganshin, A. A. Bikmukhametova, A. V. Gerasimov, V. V. Gorbatchuk, S. A. Ziganshina, A. A. Bukharaev. The effect of substrate and air humidity on morphology of films of L-leucyl-L-leucine dipeptide. Protection of Metals and Physical Chemistry of Surfaces 2014, 50 (1) , 49-54. https://doi.org/10.1134/S2070205114010171
    35. Goulnaz D. Safina, Marat A. Ziganshin, Aidar T. Gubaidullin, Valery V. Gorbatchuk. Analysis of guest binary mixtures by tert-butylcalix[6]arene using host memory of previously bound guests. Organic & Biomolecular Chemistry 2013, 11 (8) , 1318. https://doi.org/10.1039/c2ob27164h
    36. Gabriele Giancane, Victor Borovkov, Yoshihisa Inoue, Sabrina Conoci, Ludovico Valli. Syn–anti conformation switching of a bis-porphyrin derivative at the air–water interface and in the solid state as an effective tool for chemical sensing. Soft Matter 2013, 9 (7) , 2302. https://doi.org/10.1039/c2sm27141a
    37. Amir A. Khabibullin, Goulnaz D. Safina, Marat A. Ziganshin, Valery V. Gorbatchuk. Thermal analysis of charge-transfer complex formed by nitrogen dioxide and substituted calix[4]arene. Journal of Thermal Analysis and Calorimetry 2012, 110 (3) , 1309-1313. https://doi.org/10.1007/s10973-011-2105-5
    38. Marat A. Ziganshin, Irina G. Efimova, Valery V. Gorbatchuk, Sufia A. Ziganshina, Anton P. Chuklanov, Anastas A. Bukharaev, Dmitry V. Soldatov. Interaction of l ‐leucyl‐ l ‐leucyl‐ l ‐leucine thin film with water and organic vapors: receptor properties and related morphology. Journal of Peptide Science 2012, 18 (4) , 209-214. https://doi.org/10.1002/psc.1431
    39. Goulnaz D. Safina, Olga M. Gavrilova, Marat A. Ziganshin, Ivan I. Stoikov, Igor S. Antipin, Valery V. Gorbatchuk. Molecular recognition of chloroform by divergent polymorphic transitions in tert-butylthiacalix[4]arene tetrasubstituted with N-(2-hydroxyethyl)carbamoylmethoxy groups in a lower rim. Mendeleev Communications 2011, 21 (5) , 291-292. https://doi.org/10.1016/j.mencom.2011.09.022
    40. Alexander V. Gerasimov, Marat A. Ziganshin, Alexander E. Vandyukov, Valeri I. Kovalenko, Valery V. Gorbatchuk, Anne-Marie Caminade, Jean-Pierre Majoral. Specific vapor sorption properties of phosphorus-containing dendrimers. Journal of Colloid and Interface Science 2011, 360 (1) , 204-210. https://doi.org/10.1016/j.jcis.2011.04.017
    41. Tobias Gruber, Conrad Fischer, Wilhelm Seichter, Petra Bombicz, Edwin Weber. Upper rim site lipophilic calix[4]arenes as receptors for natural terpenes and functionally related solvent molecules: combined crystal structure and QMB sensor study. CrystEngComm 2011, 13 (5) , 1422-1431. https://doi.org/10.1039/C0CE00696C
    42. Goulnaz D. Safina, Laura R. Validova, Marat A. Ziganshin, Ivan I. Stoikov, Igor S. Antipin, Valery V. Gorbatchuk. Using clathrate pseudopolymorphism for a single sensor detection of target component in the headspace of liquid mixture. Sensors and Actuators B: Chemical 2010, 148 (1) , 264-268. https://doi.org/10.1016/j.snb.2010.04.032
    43. I. G. Efimova, M. A. Ziganshin, V. V. Gorbatchuk, D. V. Soldatov, S. A. Ziganshina, A. P. Chuklanov, A. A. Bukharaev. Formation of nanoislands on the surface of thin dipeptide films under the effect of vaporous organic compounds. Protection of Metals and Physical Chemistry of Surfaces 2009, 45 (5) , 525-528. https://doi.org/10.1134/S2070205109050049
    44. G. D. Safina, M. A. Ziganshin, I. I. Stoikov, I. S. Antipin, V. V. Gorbachuk. Configuration effect of the tert-butylthiacalix[4]arene tetracarboxy derivative on its receptor properties toward vaporous organic compounds. Russian Chemical Bulletin 2009, 58 (1) , 71-79. https://doi.org/10.1007/s11172-009-0011-9
    Download PDF
    Go to The Journal of Physical Chemistry B
    Get e-Alerts
    Get e-Alerts

    The Journal of Physical Chemistry B

    Cite this: J. Phys. Chem. B 2008, 112, 49, 15569–15575
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jp804277u
    Published November 14, 2008
    Copyright © 2008 American Chemical Society
    Request reuse permissions

    Article Views

    559

    Altmetric

    -

    Citations

    44
    Learn about these metrics

    Article Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.

    Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.

    The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated.