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Cited by 121Advanced Chemical Sensor TechnologiesGas Sensing Nanomaterials and SensorsAnalytical Chemistry and Chromatography

An Enantioselective e‐Nose: An Array of Nanoporous Homochiral MOF Films for Stereospecific Sensing of Chiral Odors

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Okur, Salih, Qin, Peng, Chandresh, Abhinav, Li, Chun, Zhang, Zejun, Lemmer, Ulrich, Heinke, Lars·2021·Angewandte Chemie International Edition
DOI 10.1002/anie.202013227PMC PMC7898876
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Abstract

Chirality is essential in nature and often pivotal for biological information transfer, for example, via odor messenger molecules. While the human nose can distinguish the enantiomers of many chiral odors, the technical realization by an artificial sensor or an electronic nose, e-nose, remains a challenge. Herein, we present an array of six sensors coated with nanoporous metal-organic framework (MOF) films of different homochiral and achiral structures, working as an enantioselective e-nose. While the achiral-MOF-film sensors show identical responses for both isomers of one chiral odor molecule, the responses of the homochiral MOF films differ for different enantiomers. By machine learning algorithms, the combined array data allow the stereoselective identification of all compounds, here tested for five pairs of chiral odor molecules. We foresee the chiral-MOF-e-nose, able to enantioselectively detect and discriminate chiral odors, to be a powerful approach towards advanced odor sensing.

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  • SURMOFs coated on a QCM adsorb VOCs on the outer surface as well as inside the pores.

    “SURMOFs coated on a QCM adsorb the VOCs on the outer surface as well as inside the pores (see Figure 3) [30].”

    From Sniff Species: SURMOF-Based Sensor Array Discriminates Aromatic Plants beyond the Genus Level (2021) · cites this paper as [30]

    The passage labeled Abstract (page not provided) describes QCM sensors coated with nanoporous SURMOFs and says their frequency shifts reflect uptake of VOC molecules by the MOF films. It does not establish the claim that VOCs adsorb on the outer surface as well as inside the pores; in particular, it does not identify outer-surface adsorption. (LLM, conf=0.83)

    Experimental — accuracy not yet measured

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Research works printed but not linked: 57

  1. L. D. Barron, Space Sci. Rev. 2008, 135, 187– 201;
  2. A. Salam, J. Mol. Evol. 1991, 33, 105– 113;
  3. L. A. Nguyen, H. He, C. Pham-Huy, Int. J. Biomed. Sci. 2006, 2, 85– 100. 23674971 PMC3614593
  4. [2]K. Mori, Bioorg. Med. Chem. 2007, 15, 7505– 7523. 17855097
  5. [3]J. H. Tumlinson, M. G. Klein, R. E. Doolittle, T. L. Ladd, A. T. Proveaux, Science 1977, 197, 789– 792. 17790774
  6. [4]R. Bentley, Chem. Rev. 2006, 106, 4099– 4112. 16967929
  7. [6]E. Brenna, C. Fuganti, S. Serra, Tetrahedron: Asymmetry 2003, 14, 1– 42.
  8. [7]A. Berthod, Chiral Recognition in Separation Methods: Mechanisms and Applications, Springer Berlin Heidelberg, Berlin, 2010.
  9. L. Torsi, G. M. Farinola, F. Marinelli, M. C. Tanese, O. H. Omar, L. Valli, F. Babudri, F. Palmisano, P. G. Zambonin, F. Naso, Nat. Mater. 2008, 7, 412– 417; 18425136
  10. N. M. Maier, W. Lindner, Anal. Bioanal. Chem. 2007, 389, 377– 397. 17632705
  11. [9]G. A. Hembury, V. V. Borovkov, Y. Inoue, Chem. Rev. 2008, 108, 1– 73. 18095713
  12. C. Fietzek, T. Hermle, W. Rosenstiel, V. Schurig, Fresenius J. Anal. Chem. 2001, 371, 58– 63; 11605760
  13. K. Bodenhöfer, A. Hierlemann, M. Juza, V. Schurig, W. Göpel, Anal. Chem. 1997, 69, 4017– 4031; 9322439
  14. P. Kurzawski, V. Schurig, A. Hierlemann, Anal. Chem. 2009, 81, 9353– 9364; 19842695
  15. C. Xu, S. C. Ng, H. S. O. Chan, Langmuir 2008, 24, 9118– 9124. 18616230
  16. N. J. Kybert, M. B. Lerner, J. S. Yodh, G. Preti, A. T. C. Johnson, ACS Nano 2013, 7, 2800– 2807; 23442175
  17. S. M. Khamis, R. A. Jones, A. T. C. Johnson, G. Preti, J. Kwak, A. Gelperin, AIP Adv. 2012, 2, 022110.
  18. [12]Y. Zhang, X. Liu, S. Qiu, Q. Zhang, W. Tang, H. Liu, Y. Guo, Y. Ma, X. Guo, Y. Liu, J. Am. Chem. Soc. 2019, 141, 14643– 14649. 31448915
  19. [13]M. L. Lu, W. G. Zhang, S. Zhang, J. Fan, W. C. Su, X. Yin, Chirality 2010, 22, 411– 415. 19603481
  20. [14]K. Haupt, K. Noworyta, W. Kutner, Anal. Commun. 1999, 36, 391– 393.
  21. H. S. Guo, J. M. Kim, S. M. Chang, W. S. Kim, Biosens. Bioelectron. 2009, 24, 2931– 2934; 19282168
  22. F. Temel, S. Erdemir, B. Tabakci, M. Akpinar, M. Tabakci, Anal. Bioanal. Chem. 2019, 411, 11. 30931505
  23. [16]P. Z. Moghadam, A. Li, S. B. Wiggin, A. Tao, A. G. P. Maloney, P. A. Wood, S. C. Ward, D. Fairen-Jimenez, Chem. Mater. 2017, 29, 2618– 2625.
  24. [17]S. Kaskel, The Chemistry of Metal–Organic Frameworks: Synthesis Characterization, and Applications, Wiley, Hoboken, 2016.
  25. [18]M. Padmanaban, P. Muller, C. Lieder, K. Gedrich, R. Grunker, V. Bon, I. Senkovska, S. Baumgartner, S. Opelt, S. Paasch, E. Brunner, F. Glorius, E. Klemm, S. Kaskel, Chem. Commun. 2011, 47, 12089– 12091. 21960280
  26. T. Duerinck, J. F. M. Denayer, Chem. Eng. Sci. 2015, 124, 179– 187;
  27. P. Peluso, V. Mamane, S. Cossu, J. Chromatogr. A 2014, 1363, 11– 26; 25001329
  28. N. Corella-Ochoa, J. B. Tapia, H. N. Rubin, V. Lillo, J. Gonzalez-Cobos, J. L. Nunez-Rico, S. R. G. Balestra, N. Almora-Barrios, M. Lledos, A. Guell-Bara, J. Cabezas-Gimenez, E. C. Escudero-Adan, A. Vidal-Ferran, S. Calero, M. Reynolds, C. Marti-Gastaldo, J. R. Galan-Mascaros, J. Am. Chem. Soc. 2019, 141, 14306– 14316; 31426632
  29. Y. A. Satska, E. A. Mikhalyova, Z. V. Chernenko, S. V. Kolotilov, M. Zeller, I. V. Komarov, A. V. Tymtsunik, A. Tolmachev, K. S. Gavrilenko, A. W. Addison, RSC Adv. 2016, 6, 93707– 93714.
  30. [20]H. J. Duan, C. X. Yang, X. P. Yan, RSC Adv. 2015, 5, 30577– 30582.
  31. D. James, S. M. Scott, Z. Ali, W. T. O'Hare, Microchim. Acta 2005, 149, 1– 17;
  32. F. Röck, N. Barsan, U. Weimar, Chem. Rev. 2008, 108, 705– 725; 18205411
  33. M. Peris, L. Escuder-Gilabert, Trends Food Sci. Technol. 2016, 58, 40– 54.
  34. [22]K. Mori, Chirality 1998, 10, 578– 586.
  35. [23]G. Ohloff, Helv. Chim. Acta 1992, 75, 2041– 2108.
  36. M. Mirasoli, R. Gotti, M. Di Fusco, A. Leoni, C. Colliva, A. Roda, Talanta 2014, 129, 32– 38; 25127562
  37. G. P. Blanch, M. D. Caja, M. L. R. del Castillo, M. Herraiz, Eur. Food Res. Technol. 1999, 210, 139– 143.
  38. J. A. Gustafson, C. E. Wilmer, Sens. Actuators B 2018, 267, 483– 493;
  39. A. Sturluson, R. Sousa, Y. Zhang, M. T. Huynh, C. Laird, A. H. P. York, C. Silsby, C.-H. Chang, C. M. Simon, ACS Appl. Mater. Interfaces 2020, 12, 6546– 6564; 31918544
  40. S. Okur, Z. Zhang, M. Sarheed, P. Nick, U. Lemmer, L. Heinke, Sens. Actuators B 2020, 306, 127502.
  41. O. Shekhah, H. Wang, S. Kowarik, F. Schreiber, M. Paulus, M. Tolan, C. Sternemann, F. Evers, D. Zacher, R. A. Fischer, C. Wöll, J. Am. Chem. Soc. 2007, 129, 15118– 15119; 18020338
  42. L. Heinke, C. Wöll, Adv. Mater. 2019, 31, 1806324. 30701602
  43. [27]S. Güney, A. Atasoy, Sens. Actuators B 2012, 166, 721– 725.
  44. [28]Z. Gu, S. Grosjean, S. Bräse, C. Wöll, L. Heinke, Chem. Commun. 2015, 51, 8998– 9001. 25940393
  45. [29]S. S. Y. Chui, S. M. F. Lo, J. P. H. Charmant, A. G. Orpen, I. D. Williams, Science 1999, 283, 1148– 1150. 10024237
  46. [30]J. X. Liu, B. Lukose, O. Shekhah, H. K. Arslan, P. Weidler, H. Gliemann, S. Bräse, S. Grosjean, A. Godt, X. L. Feng, K. Mullen, I. B. Magdau, T. Heine, C. Wöll, Sci. Rep. 2012, 2, 921. 23213357 PMC3513965
  47. [31]Z. Gu, L. Heinke, C. Wöll, T. Neumann, W. Wenzel, Q. Li, K. Fink, O. D. Gordan, D. R. T. Zahn, Appl. Phys. Lett. 2015, 107, 183301.
  48. [32]D. Johannsmann, The Quartz Crystal Microbalance in Soft Matter Research, Springer, Berlin 2015.
  49. [33]J. A. Gustafson, C. E. Wilmer, ACS Sens. 2019, 4, 1586– 1593. 31124354
  50. [34]A. Kirchon, L. Feng, H. F. Drake, E. A. Joseph, H.-C. Zhou, Chem. Soc. Rev. 2018, 47, 8611– 8638. 30234863
  51. [35]C. Phat, B. Moon, C. Lee, Food Chem. 2016, 192, 1068– 1077. 26304449
  52. P. Shahgaldian, U. Pieles, Sensors 2006, 6, 593– 615;
  53. M. Jung, D. Schmalzing, V. Schurig, J. Chromatogr. 1991, 552, 43– 57;
  54. V. Schurig, Molecules 2016, 21, 1535. PMC6274307 27854299
  55. R. Bueno-Perez, A. Martin-Calvo, P. Gomez-Alvarez, J. J. Gutierrez-Sevillano, P. J. Merkling, T. J. H. Vlugt, T. S. van Erp, D. Dubbeldam, S. Calero, Chem. Commun. 2014, 50, 10849– 10852; 25090236
  56. X. Bao, L. J. Broadbelt, R. Q. Snurr, Phys. Chem. Chem. Phys. 2010, 12, 6466– 6473; 20498862
  57. S.-Y. Zhang, D. Fairen-Jimenez, M. J. Zaworotko, Angew. Chem. Int. Ed. 2020, 59, 17600– 17606; PMC7540565 32589318 Angew. Chem. 2020, 132, 17753– 17759.

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Authors
Okur, S., Qin, P., Chandresh, A., Li, C., Zhang, Z., Lemmer, U., & Heinke, L.
Affiliations
  • Karlsruhe Institute of Technology (DE)
  • Karlsruhe Institute of Technology (KIT) Light Technology Institute (LTI) Engesserstrasse 13 76131 Karlsruhe Germany
Corresponding author
Heinke, Lars
ORCID
Venue
Angewandte Chemie International Edition
Publisher
Wiley
Published
2020-12-15
Volume
60
Issue
7
Pages
3566-3571
ISSN
  • 1433-7851 (ISSN-L)
  • 1521-3773
DOI
10.1002/anie.202013227
PMC
PMC7898876
OpenAlex
W3097473180
Cited by
121
References
2
Citations by year
2026: 9 · 2025: 19 · 2024: 23 · 2023: 27 · 2022: 20 · 2021: 22 · 2020: 1
FWCI
5.50
Type
journal article
Language
en
Open access
Licence
Locations
  • Angewandte Chemie International Edition (publishedVersion, cc-by-nc)
  • PubMed Central (publishedVersion, cc-by-nc)
  • PubMed (publishedVersion)
  • Repository KITopen (Karlsruhe Institute of Technology) (submittedVersion, cc-by-nc)
  • KITopen
Funders
  • Deutsche Forschungsgemeinschaft (HE 7036/5)
  • Alexander von Humboldt-Stiftung
  • China Scholarship Council
Topics
  • Physical Sciences › Engineering › Biomedical Engineering › Advanced Chemical Sensor Technologies
  • Physical Sciences › Engineering › Electrical and Electronic Engineering › Gas Sensing Nanomaterials and Sensors
  • Physical Sciences › Chemistry › Spectroscopy › Analytical Chemistry and Chromatography
Keywords
homochiral metal-organic frameworks, odor discrimination, machine learning classification, gas sensor arrays
MeSH terms
Metal-Organic Frameworks, Humans, Odorants, Stereoisomerism, Molecular Structure, Nanopores, Electronic Nose

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