{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,2,21]],"date-time":"2025-02-21T16:41:14Z","timestamp":1740156074048,"version":"3.37.3"},"reference-count":71,"publisher":"MDPI AG","issue":"5","license":[{"start":{"date-parts":[[2020,4,26]],"date-time":"2020-04-26T00:00:00Z","timestamp":1587859200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001659","name":"Deutsche Forschungsgemeinschaft","doi-asserted-by":"publisher","award":["HE 7036\/5"],"id":[{"id":"10.13039\/501100001659","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Symmetry"],"abstract":"Chiral nanoporous solids are a fascinating class of materials, allowing efficient enantiomer separation. Here, we review the status, applications, and potential of thin films of homochiral metal\u2013organic frameworks (MOFs). Combining the advantages of MOFs, whose well-defined, crystalline structures can be rationally tuned, with the benefits of thin films enables new opportunities for the characterization of the enantioselectivity, e.g., via chiroptical spectroscopy and straightforward molecular uptake quantifications. By incorporating photoresponsive molecules in the chiral MOF films, the enantioselectivity of the material can be dynamically remote-controlled. The most promising application of MOF films is their use as membranes, where the enantioselective separation of chiral molecules is demonstrated and parameters for further improvements are discussed.<\/jats:p>","DOI":"10.3390\/sym12050686","type":"journal-article","created":{"date-parts":[[2020,4,29]],"date-time":"2020-04-29T05:29:15Z","timestamp":1588138155000},"page":"686","source":"Crossref","is-referenced-by-count":10,"title":["Thin Films of Homochiral Metal\u2013Organic Frameworks for Chiroptical Spectroscopy and Enantiomer Separation"],"prefix":"10.3390","volume":"12","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-5819-3357","authenticated-orcid":false,"given":"Chun","family":"Li","sequence":"first","affiliation":[{"name":"Karlsruhe Institute of Technology (KIT), Institute of Functional Interfaces (IFG), Hermann-von-Helmholtz-Platz 1, 76344 Eggenstein-Leopoldshafen, Germany"}]},{"given":"Lars","family":"Heinke","sequence":"additional","affiliation":[{"name":"Karlsruhe Institute of Technology (KIT), Institute of Functional Interfaces (IFG), Hermann-von-Helmholtz-Platz 1, 76344 Eggenstein-Leopoldshafen, Germany"}]}],"member":"1968","published-online":{"date-parts":[[2020,4,26]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"341","DOI":"10.1146\/annurev.anchem.111808.073635","article-title":"Chiral separations","volume":"3","author":"Stalcup","year":"2010","journal-title":"Ann. Rev. Anal. Chem."},{"key":"ref_2","doi-asserted-by":"crossref","unstructured":"Yaghi, O.M., Kalmutzki, M.J., and Diercks, C.S. (2019). Introduction to Reticular Chemistry: Metal-Organic Frameworks and Covalent Organic Frameworks, John Wiley & Sons.","DOI":"10.1002\/9783527821099"},{"key":"ref_3","doi-asserted-by":"crossref","unstructured":"Kaskel, S. (2016). The Chemistry of Metal-Organic Frameworks, 2 Volume Set: Synthesis, Characterization, and Applications, John Wiley & Sons.","DOI":"10.1002\/9783527693078"},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"3279","DOI":"10.1021\/ja9819918","article-title":"Helical coordination polymers from achiral components in crystals. Homochiral crystallization, homochiral helix winding in the solid state, and chirality control by seeding","volume":"121","author":"Ezuhara","year":"1999","journal-title":"J. Am. Chem. Soc."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"4112","DOI":"10.1002\/adma.201000197","article-title":"Engineering homochiral metal-organic frameworks for heterogeneous asymmetric catalysis and enantioselective separation","volume":"22","author":"Liu","year":"2010","journal-title":"Adv. Mater."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"90","DOI":"10.1002\/cite.201000188","article-title":"Chiral metal-organic frameworks and their application in asymmetric catalysis and stereoselective separation","volume":"83","author":"Nickerl","year":"2011","journal-title":"Chem. Ing. Tech."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"2292","DOI":"10.1021\/jacs.5b12860","article-title":"CD-MOF: A Versatile Separation Medium","volume":"138","author":"Hartlieb","year":"2016","journal-title":"J. Am. Chem. Soc."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"12089","DOI":"10.1039\/c1cc14893a","article-title":"Application of a chiral metal-organic framework in enantioselective separation","volume":"47","author":"Padmanaban","year":"2011","journal-title":"Chem. Commun."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"8475","DOI":"10.1002\/anie.200703443","article-title":"Chiral symmetry breaking by chemically manipulating statistical fluctuation in crystallization","volume":"46","author":"Wu","year":"2007","journal-title":"Angew. Chem. Int. Edi."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"1315","DOI":"10.1039\/b802258p","article-title":"Postsynthetic modification of metal-organic frameworks","volume":"38","author":"Wang","year":"2009","journal-title":"Chem. Soc. Rev."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"7524","DOI":"10.1021\/ja901440g","article-title":"Postsynthetic modification switches an achiral framework to catalytically active homochiral metal-organic porous materials","volume":"131","author":"Banerjee","year":"2009","journal-title":"J. Am. Chem. Soc."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"3072","DOI":"10.1039\/c2dt12153k","article-title":"\u201cClick\u201d post-synthetic modification of metal-organic frameworks with chiral functional adduct for heterogeneous asymmetric catalysis","volume":"41","author":"Zhu","year":"2012","journal-title":"Dalton Trans."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1080\/01614940.2014.864145","article-title":"Metal-organic frameworks as selective or chiral oxidation catalysts","volume":"56","author":"Leus","year":"2014","journal-title":"Catal. Rev."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"3122","DOI":"10.1039\/C6CS00051G","article-title":"Chiral chemistry of metal-camphorate frameworks","volume":"45","author":"Gu","year":"2016","journal-title":"Chem. Soc. Rev."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"11","DOI":"10.1016\/j.chroma.2014.06.064","article-title":"Homochiral metal-organic frameworks and their application in chromatography enantioseparations","volume":"1363","author":"Peluso","year":"2014","journal-title":"J. Chromatogr. A"},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"179","DOI":"10.1016\/j.ces.2014.10.012","article-title":"Metal-organic frameworks as stationary phases for chiral chromatographic and membrane separations","volume":"124","author":"Duerinck","year":"2015","journal-title":"Chem. Eng. Sci."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"10434","DOI":"10.1002\/slct.201802086","article-title":"Homochiral metal organic frameworks and their usage for the enantio-purification of racemic drugs","volume":"3","author":"Ullah","year":"2018","journal-title":"ChemistrySelect"},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"10569","DOI":"10.1039\/c3cc42376j","article-title":"\u201cSingle nickel source\u201d in situ fabrication of a stable homochiral MOF membrane with chiral resolution properties","volume":"49","author":"Kang","year":"2013","journal-title":"Chem. Commun."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"15118","DOI":"10.1021\/ja076210u","article-title":"Step-by-step route for the synthesis of metal-organic frameworks","volume":"129","author":"Shekhah","year":"2007","journal-title":"J. Am. Chem. Soc."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"e1806324","DOI":"10.1002\/adma.201806324","article-title":"Surface-mounted metal-organic frameworks: Crystalline and porous molecular assemblies for fundamental insights and advanced applications","volume":"31","author":"Heinke","year":"2019","journal-title":"Adv. Mater."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"4562","DOI":"10.1038\/ncomms5562","article-title":"The surface barrier phenomenon at the loading of metal-organic frameworks","volume":"5","author":"Heinke","year":"2014","journal-title":"Nat. Commun."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"7257","DOI":"10.1039\/b811010g","article-title":"The controlled growth of oriented metal-organic frameworks on functionalized surfaces as followed by scanning force microscopy","volume":"10","author":"Munuera","year":"2008","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"82","DOI":"10.1016\/j.micromeso.2015.02.048","article-title":"Transparent films of metal-organic frameworks for optical applications","volume":"211","author":"Gu","year":"2015","journal-title":"Micropor. Mesopor. Mat."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"37463","DOI":"10.1021\/acsami.7b12045","article-title":"Defects as color centers: The apparent color of metal-organic frameworks containing Cu2+-based paddle-wheel units","volume":"9","author":"Fink","year":"2017","journal-title":"ACS Appl. Mater. Inter."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"153","DOI":"10.1039\/C8SC03735C","article-title":"Dissolving uptake-hindering surface defects in metal-organic frameworks","volume":"10","author":"Vankova","year":"2019","journal-title":"Chem. Sci."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"877","DOI":"10.1039\/c0sc00582g","article-title":"Asymmetric catalytic reactions by NbO-type chiral metal\u2013organic frameworks","volume":"2","author":"Jeong","year":"2011","journal-title":"Chem. Sci."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"5083","DOI":"10.1021\/cm071689a","article-title":"Comparative study of homochiral and racemic chiral metal-organic frameworks built from camphoric acid","volume":"19","author":"Zhang","year":"2007","journal-title":"Chem. Mater."},{"key":"ref_28","doi-asserted-by":"crossref","unstructured":"Rodger, A., and Nord\u00e9n, B. (1997). Circular Dichroism and Linear Dichroism, Oxford University Press.","DOI":"10.1093\/oso\/9780198558972.001.0001"},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"4796","DOI":"10.1039\/C5CC00694E","article-title":"Planar-chiral building blocks for metal-organic frameworks","volume":"51","author":"Cakici","year":"2015","journal-title":"Chem. Commun."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"491","DOI":"10.1002\/chir.20404","article-title":"Wavelength shifts in solid-state circular dichroism spectra: A possible explanation","volume":"19","author":"Castiglioni","year":"2007","journal-title":"Chirality"},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"9879","DOI":"10.1002\/chem.201403524","article-title":"Oriented circular dichroism analysis of chiral surface-anchored metal-organic frameworks grown by liquid-phase epitaxy and upon loading with chiral guest compounds","volume":"20","author":"Gu","year":"2014","journal-title":"Chem. Eur. J."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"2992","DOI":"10.1039\/c3cc40819a","article-title":"Simultaneously high gravimetric and volumetric methane uptake characteristics of the metal-organic framework NU-111","volume":"49","author":"Peng","year":"2013","journal-title":"Chem. Commun."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"10559","DOI":"10.1039\/C6CC04790D","article-title":"Exceptional gravimetric and volumetric CO2 uptake in a palladated NbO-type mof utilizing cooperative acidic and basic, metal-CO2 interactions","volume":"52","author":"Spanopoulos","year":"2016","journal-title":"Chem. Commun."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"333","DOI":"10.1038\/nmat3917","article-title":"Microimaging of transient guest profiles to monitor mass transfer in nanoporous materials","volume":"13","author":"Binder","year":"2014","journal-title":"Nat. Mater."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"340","DOI":"10.1016\/j.micromeso.2009.06.006","article-title":"Exploring the nature of surface barriers on MOF Zn(tbip) by applying ir microscopy in high temporal and spatial resolution","volume":"129","author":"Chmelik","year":"2010","journal-title":"Micropor. Mesopor. Mat."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"025098","DOI":"10.1088\/2053-1583\/aa6fc6","article-title":"2D zirconium-based metal-organic framework nanosheets for highly sensitive detection of mucin 1: Consistency between electrochemical and surface plasmon resonance methods","volume":"4","author":"He","year":"2017","journal-title":"2D Mater."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"3046","DOI":"10.1039\/b916953a","article-title":"Sorption behavior of an oriented surface-grown MOF-film studied by in situ X-ray diffraction","volume":"20","author":"Scherb","year":"2010","journal-title":"J. Mater. Chem."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"975","DOI":"10.1007\/s11814-018-0231-0","article-title":"Surface-enhanced infrared detection of benzene in air using a porous metal-organic-frameworks film","volume":"36","author":"Kim","year":"2019","journal-title":"Korean J. Chem. Eng."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"3548","DOI":"10.1002\/cphc.201701023","article-title":"Multi-component uptake of dye molecules by films of nanoporous metal-organic frameworks","volume":"18","author":"Saghanejhadtehrani","year":"2017","journal-title":"Chemphyschem"},{"key":"ref_40","doi-asserted-by":"crossref","unstructured":"Johannsmann, D. (2015). The Quartz Crystal Microbalance in Soft Matter Research. Fundamentals and Modeling, Springer International Publishing.","DOI":"10.1007\/978-3-319-07836-6"},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"3767","DOI":"10.3390\/ma8063767","article-title":"Liquid- and gas-phase diffusion of ferrocene in thin films of metal-organic frameworks","volume":"8","author":"Zhou","year":"2015","journal-title":"Materials"},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"193004","DOI":"10.1088\/1361-6463\/aa65f8","article-title":"Diffusion and photoswitching in nanoporous thin films of metal-organic frameworks","volume":"50","author":"Heinke","year":"2017","journal-title":"J. Phys. D App. Phys."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"807","DOI":"10.1002\/anie.201104240","article-title":"Enantiopure metal-organic framework thin films: Oriented SURMOF growth and enantioselective adsorption","volume":"51","author":"Liu","year":"2012","journal-title":"Angew. Chem. Int. Edi."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"8998","DOI":"10.1039\/C5CC02706C","article-title":"Enantioselective adsorption in homochiral metal-organic frameworks: The pore size influence","volume":"51","author":"Gu","year":"2015","journal-title":"Chem. Commun."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"9964","DOI":"10.1002\/chem.201501315","article-title":"Engineering homochiral metal-organic frameworks by spatially separating 1D chiral metal-peptide ladders: Tuning the pore size for enantioselective adsorption","volume":"21","author":"Stylianou","year":"2015","journal-title":"Chem. Eur. J."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"1119","DOI":"10.1351\/pac199163081119","article-title":"Resolution of chiral drugs","volume":"63","author":"Porter","year":"1991","journal-title":"Pure Appl. Chem."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"1218","DOI":"10.1002\/anie.201302823","article-title":"Processes to separate enantiomers","volume":"53","author":"Lorenz","year":"2014","journal-title":"Angew. Chem. Int. Edi."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"33","DOI":"10.1016\/j.chroma.2016.07.050","article-title":"Preparative supercritical fluid chromatography: A powerful tool for chiral separations","volume":"1467","author":"Speybrouck","year":"2016","journal-title":"J. Chromatogr. A"},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"284","DOI":"10.1016\/j.memsci.2010.12.001","article-title":"Ethene\/ethane separation by the MOF membrane ZIF-8: Molecular correlation of permeation, adsorption, diffusion","volume":"369","author":"Bux","year":"2011","journal-title":"J. Membrane Sci."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"8592","DOI":"10.1021\/la401471g","article-title":"Ethene\/ethane and propene\/propane separation via the olefin and paraffin selective metal-organic framework adsorbents CPO-27 and ZIF-8","volume":"29","author":"Barth","year":"2013","journal-title":"Langmuir"},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"207","DOI":"10.1016\/j.seppur.2015.08.020","article-title":"Opportunities and challenges of MOF-based membranes in gas separations","volume":"152","author":"Adatoz","year":"2015","journal-title":"Sep. Purif. Technol."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"7022","DOI":"10.1039\/c2cc32595k","article-title":"A homochiral metal-organic framework membrane for enantioselective separation","volume":"48","author":"Wang","year":"2012","journal-title":"Chem. Commun."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"27332","DOI":"10.1021\/acsami.6b09196","article-title":"Chiral chemistry of homochiral porous thin film with different growth orientations","volume":"8","author":"Chen","year":"2016","journal-title":"ACS Appl. Mater. Inter."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"8776","DOI":"10.1039\/C9CC02849H","article-title":"Switching the enantioselectivity of nanoporous host materials by light","volume":"55","author":"Kanj","year":"2019","journal-title":"Chem. Commun."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"30577","DOI":"10.1039\/C5RA01204J","article-title":"Chiral metal\u2013organic framework coated quartz crystal microbalance for chiral discrimination","volume":"5","author":"Duan","year":"2015","journal-title":"RSC Adv."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"4364","DOI":"10.1002\/aic.14194","article-title":"Fabrication of homochiral metal-organic framework membrane for enantioseparation of racemic diols","volume":"59","author":"Huang","year":"2013","journal-title":"AIChE J."},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"60","DOI":"10.1002\/apj.1943","article-title":"Preparation and characterization of Ni2(mal)2(bpy) homochiral MOF membrane","volume":"11","author":"Li","year":"2016","journal-title":"Asia Pac. J. Chem. Eng."},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"2294","DOI":"10.1002\/chem.201606056","article-title":"Sprayable, large-area metal-organic framework films and membranes of varying thickness","volume":"23","author":"Hurrle","year":"2017","journal-title":"Chem. Eur. J."},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"9781","DOI":"10.1039\/C6CC04310K","article-title":"Alignment of paired molecules of C60 within a hexagonal platform networked through hydrogen-bonds","volume":"52","author":"Hisaki","year":"2016","journal-title":"Chem. Commun."},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"16928","DOI":"10.1002\/anie.201910408","article-title":"Homochiral MOF-polymer mixed matrix membranes for efficient separation of chiral molecules","volume":"58","author":"Lu","year":"2019","journal-title":"Angew. Chem. Int. Edi."},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"8629","DOI":"10.1002\/anie.201804383","article-title":"Chiral recognition and separation by chirality-enriched metal-organic frameworks","volume":"57","author":"Das","year":"2018","journal-title":"Angew. Chem. Int. Edi."},{"key":"ref_62","doi-asserted-by":"crossref","unstructured":"Berthod, A. (2010). Chiral Recognition in Separation Methods, Springer.","DOI":"10.1007\/978-3-642-12445-7"},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"1700239","DOI":"10.1002\/marc.201700239","article-title":"Stimuli-responsive metal-organic frameworks with photoswitchable azobenzene side groups","volume":"39","author":"Kanj","year":"2018","journal-title":"Macromol. Rapid Commun."},{"key":"ref_64","doi-asserted-by":"crossref","unstructured":"Haldar, R., Heinke, L., and W\u00f6ll, C. (2019). Advanced photoresponsive materials using the metal-organic framework approach. Adv. Mater., e1905227\u2013e1905256.","DOI":"10.1002\/adma.201905227"},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"3779","DOI":"10.1002\/cphc.201500829","article-title":"Photoswitchable adsorption in metal-organic frameworks based on polar guest-host interactions","volume":"16","author":"Wang","year":"2015","journal-title":"Chemphyschem"},{"key":"ref_66","doi-asserted-by":"crossref","first-page":"118","DOI":"10.1016\/j.micromeso.2011.08.008","article-title":"Computational screening of homochiral metal\u2013organic frameworks for enantioselective adsorption","volume":"157","author":"Bao","year":"2012","journal-title":"Micropor. Mesopor. Mater."},{"key":"ref_67","doi-asserted-by":"crossref","first-page":"6466","DOI":"10.1039\/c000809e","article-title":"Elucidation of consistent enantioselectivity for a homologous series of chiral compounds in homochiral metal-organic frameworks","volume":"12","author":"Bao","year":"2010","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_68","doi-asserted-by":"crossref","first-page":"10849","DOI":"10.1039\/C4CC03745F","article-title":"Enantioselective adsorption of ibuprofen and lysine in metal-organic frameworks","volume":"50","author":"Merkling","year":"2014","journal-title":"Chem. Commun."},{"key":"ref_69","doi-asserted-by":"crossref","first-page":"6033","DOI":"10.1021\/acs.jpcc.6b09740","article-title":"Computational design of metal\u2013organic framework arrays for gas sensing: Influence of array size and composition on sensor performance","volume":"121","author":"Gustafson","year":"2017","journal-title":"J. Phys. Chem. C"},{"key":"ref_70","doi-asserted-by":"crossref","first-page":"127502","DOI":"10.1016\/j.snb.2019.127502","article-title":"Towards a MOF e-Nose: A SURMOF sensor array for detection and discrimination of plant oil scents and their mixtures","volume":"306","author":"Okur","year":"2020","journal-title":"Sens. Actuators B"},{"key":"ref_71","doi-asserted-by":"crossref","first-page":"31421","DOI":"10.1021\/acsami.9b11872","article-title":"Liquid-phase epitaxial growth of azapyrene-based chiral metal-organic framework thin films for circularly polarized luminescence","volume":"11","author":"Chen","year":"2019","journal-title":"ACS Appl. Mater. Inter."}],"container-title":["Symmetry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/2073-8994\/12\/5\/686\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2024,6,27]],"date-time":"2024-06-27T08:43:59Z","timestamp":1719477839000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/2073-8994\/12\/5\/686"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2020,4,26]]},"references-count":71,"journal-issue":{"issue":"5","published-online":{"date-parts":[[2020,5]]}},"alternative-id":["sym12050686"],"URL":"https:\/\/doi.org\/10.3390\/sym12050686","relation":{},"ISSN":["2073-8994"],"issn-type":[{"type":"electronic","value":"2073-8994"}],"subject":[],"published":{"date-parts":[[2020,4,26]]}}}