{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,6,12]],"date-time":"2026-06-12T07:43:21Z","timestamp":1781250201368,"version":"3.54.1"},"reference-count":61,"publisher":"MDPI AG","issue":"4","license":[{"start":{"date-parts":[[2019,2,22]],"date-time":"2019-02-22T00:00:00Z","timestamp":1550793600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Salicylideneaniline (SA) sorbed in cation-exchanged M-ZSM-5 (M = H+, Li+, Na+, K+, Rb+, Cs+ and Zn2+) zeolites was studied by spectroscopic techniques assisted by quantum-chemical calculations. The nature of extra-framework cations present in the zeolite void was found to affect the spectral signature of the sorbed SA molecule that points to the shift of tautomeric equilibrium between the enol and keto forms. Small size cations, such as H+ and Li+, stabilize a cis-keto SA tautomer along with a enol one in the zeolite structure. The calculations indicate that the sorbed cis-keto tautomer may have the dipole large enough to be considered as a zwitterion. New features appearing in the spectra with the increase of the cation size were attributed to the presence of trans-keto SA tautomer, which up to now has been observed only in time-resolved spectroscopic experiments. A strong interaction of the molecule with cations in Zn-ZSM-5 zeolite results in the chelation of enol SA with the divalent Zn2+ ions. The results of the study suggest that the tautomeric equilibrium of molecules belonging to the Schiff base family can be tuned by the confinement in the nanoporous materials via a choice of topology of zeolite framework and the nature of extra-framework cations.<\/jats:p>","DOI":"10.3390\/molecules24040795","type":"journal-article","created":{"date-parts":[[2019,2,22]],"date-time":"2019-02-22T11:26:14Z","timestamp":1550834774000},"page":"795","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":3,"title":["A Spectroscopic Study of Tautomeric Equilibrium of Salicylideneaniline in ZSM-5 Zeolites"],"prefix":"10.3390","volume":"24","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-8163-6614","authenticated-orcid":false,"given":"Matthieu","family":"Hureau","sequence":"first","affiliation":[{"name":"LASIR\u2014Laboratoire de Spectrochimie Infrarouge et Raman, CNRS, UMR 8516, University of Lille, F-59000 Lille, France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2713-5143","authenticated-orcid":false,"given":"Alain","family":"Moissette","sequence":"additional","affiliation":[{"name":"LASIR\u2014Laboratoire de Spectrochimie Infrarouge et Raman, CNRS, UMR 8516, University of Lille, F-59000 Lille, France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8370-8797","authenticated-orcid":false,"given":"Konstantin S.","family":"Smirnov","sequence":"additional","affiliation":[{"name":"LASIR\u2014Laboratoire de Spectrochimie Infrarouge et Raman, CNRS, UMR 8516, University of Lille, F-59000 Lille, France"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2019,2,22]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"508","DOI":"10.1016\/S0022-2313(97)00078-1","article-title":"Femtosecond luminescence study of hydrogen-atom-transfer process in thermochromic crystalline salicylideneanilines","volume":"72","author":"Kobayashi","year":"1997","journal-title":"J. Lumin."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"10645","DOI":"10.1021\/jp9715888","article-title":"Femtosecond Fluorescence Study of Proton-Transfer Process in Thermochromic Crystalline Salicylideneanilines","volume":"101","author":"Sekikawa","year":"1997","journal-title":"J. Phys. Chem. B"},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"4060","DOI":"10.1021\/j100373a033","article-title":"Spectroscopic studies of the photochromic molecule N-(2-hydroxybenzylidene)aniline and its photoproduct","volume":"94","author":"Turbeville","year":"1990","journal-title":"J. Phys. Chem."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"134205","DOI":"10.1103\/PhysRevB.69.134205","article-title":"First-principles study of salicylideneaniline molecular crystals: Tautomerization reaction involving intermolecular hydrogen bonds","volume":"69","author":"Mikami","year":"2004","journal-title":"Phys. Rev. B"},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"11959","DOI":"10.1021\/jp901849a","article-title":"Comparative Investigation of Ultrafast Photoinduced Processes in Salicylidene- Aminopyridine in Solution and Solid State","volume":"113","author":"Sliwa","year":"2009","journal-title":"J. Phys. Chem. C"},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"2245","DOI":"10.1021\/j100879a027","article-title":"Spectroscopic Evidence for the Enol Imine-Keto Enamine Tautomerism of N-(o- and p-Hydroxybenzylidene) Anils in Solution","volume":"70","author":"Ledbetter","year":"1966","journal-title":"J. Phys. Chem."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"1909","DOI":"10.1246\/bcsj.50.1909","article-title":"Spectroscopic and Kinetic Studies of the Photochromism of N-Salicylideneanilines and Related Compounds","volume":"50","author":"Ryoichi","year":"1977","journal-title":"Bull. Chem. Soc. Jpn."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"2786","DOI":"10.1021\/ja00528a045","article-title":"Photochemical kinetics of salicylidenaniline","volume":"102","author":"Barbara","year":"1980","journal-title":"J. Am. Chem. Soc."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"1727","DOI":"10.1139\/v82-236","article-title":"A spectroscopic study of the solvent dependent processes of the anils of benzaldehyde and salicylaldehyde","volume":"60","author":"Lewis","year":"1982","journal-title":"Can. J. Chem."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"2449","DOI":"10.1021\/j100210a041","article-title":"Resonance Raman spectra of the tautomers of pyridoxal and salicylaldehyde Schiff bases","volume":"86","author":"Ledbetter","year":"1982","journal-title":"J. Phys. Chem."},{"key":"ref_11","doi-asserted-by":"crossref","unstructured":"Antonov, L., Fabian, W.M.F., Nedeltcheva, D., and Kamounah, F.S. (2000). Tautomerism of 2-hydroxynaphthaldehyde Schiff bases. J. Chem. Soc. Perkin Trans. 2, 1173\u20131179.","DOI":"10.1039\/b000798f"},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"2854","DOI":"10.1021\/jp803850n","article-title":"Influence of Intermolecular Hydrogen Bonding on the Photochromic Cycle of the Aromatic Schiff Base N,N\u2032-Bis(salicylidene)-p-phenylenediamine in Solution","volume":"113","author":"Karolczak","year":"2009","journal-title":"J. Phys. Chem. A"},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"269","DOI":"10.2174\/138527209787314797","article-title":"Anils: Photochromism by H-transfer","volume":"13","author":"Hadjoudis","year":"2009","journal-title":"Curr. Org. Chem."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"1453","DOI":"10.1016\/j.jlumin.2011.03.041","article-title":"p-Carboxyl-N-salicylideneanilines: Simple but efficient chromophores for one-dimensional microrods with aggregation-induced emission enhancement (AIEE) characteristics","volume":"131","author":"Chen","year":"2011","journal-title":"J. Lumin."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"6104","DOI":"10.1039\/c2jm15114f","article-title":"Novel lithium Schiff-base cluster complexes as electron injectors: Synthesis, crystal structure, thin film characterisation and their performance in OLEDs","volume":"22","author":"Kathirgamanathan","year":"2012","journal-title":"J. Mater. Chem."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"530","DOI":"10.1016\/j.molstruc.2016.12.038","article-title":"Photochromic properties of the N-Salicylideneaniline in Polyvinyl Butyral matrix: Experimental and theoretical investigations","volume":"1134","author":"Shahab","year":"2017","journal-title":"J. Mol. Struct."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"27539","DOI":"10.1021\/jp5081884","article-title":"Photoswitching of Conductance through Salicylidene Methylamine","volume":"118","author":"Staykov","year":"2014","journal-title":"J. Phys. Chem. C"},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"6898","DOI":"10.1021\/acs.jpcc.7b00580","article-title":"Assessing Density Functional Theory Approaches for Predicting the Structure and Relative Energy of Salicylideneaniline Molecular Switches in the Solid State","volume":"121","author":"Quertinmont","year":"2017","journal-title":"J. Phys. Chem. C"},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"5318","DOI":"10.1039\/C6CP08545H","article-title":"Tailoring the Schiff base photoswitching\u2014A non-adiabatic molecular dynamics study of substituent effect on excited state proton transfer","volume":"19","author":"Jankowska","year":"2017","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"201","DOI":"10.1016\/S0020-1693(00)83468-4","article-title":"Stability studies in relation to IR data of some schiff base complexes of transition metals and their biological and pharmacological studies","volume":"151","author":"Parashar","year":"1988","journal-title":"Inorg. Chim. Acta"},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"1785","DOI":"10.1016\/j.ica.2004.11.026","article-title":"Cd(II) and Cu(II) complexes of polydentate Schiff base ligands: Synthesis, characterization, properties and biological activity","volume":"358","author":"Golcu","year":"2005","journal-title":"Inorg. Chim. Acta"},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"791","DOI":"10.1002\/poc.1517","article-title":"The protective effect of hydroxyl-substituted Schiff bases on the radical-induced oxidation of DNA","volume":"22","author":"Zhao","year":"2009","journal-title":"J. Phys. Org. Chem."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"4087","DOI":"10.1021\/j100163a036","article-title":"Examination of the solventlike nature of zeolites based on solvatochromic indicator","volume":"95","author":"Dutta","year":"1991","journal-title":"J. Phys. Chem."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"2074","DOI":"10.1002\/1099-0690(200207)2002:13<2074::AID-EJOC2074>3.0.CO;2-I","article-title":"Photochemistry of Anils in NaY Zeolite","volume":"2002","author":"Casades","year":"2002","journal-title":"Eur. J. Org. Chem."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"2971","DOI":"10.1021\/jp4016036","article-title":"Initial Processes of Proton Transfer in Salicylideneaniline Studied by Time-Resolved Photoelectron Spectroscopy","volume":"117","author":"Sekikawa","year":"2013","journal-title":"J. Phys. Chem. A"},{"key":"ref_26","first-page":"579","article-title":"Photochromism and thermochromism of Schiff bases in the solid state: Structural aspects","volume":"33","author":"Hadjoudis","year":"2004","journal-title":"Chem. Soc. Rev."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"1669","DOI":"10.1002\/cphc.201100232","article-title":"Effects of a Self-Assembled Molecular Capsule on the Ultrafast Photodynamics of a Photochromic Salicylideneaniline Guest","volume":"12","author":"Sliwa","year":"2011","journal-title":"ChemPhysChem"},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"207","DOI":"10.1016\/j.jphotochemrev.2005.12.002","article-title":"Photochromism of organic compounds in the crystal state","volume":"6","author":"Amimoto","year":"2005","journal-title":"J. Photochem. Photobiol. C"},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"214308","DOI":"10.1063\/1.3032215","article-title":"Electronic-structure and quantum dynamical study of the photochromism of the aromatic Schiff base salicylideneaniline","volume":"129","author":"Gelabert","year":"2008","journal-title":"J. Chem. Phys."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"4574","DOI":"10.1021\/jp4028035","article-title":"Photodynamics of Schiff Base Salicylideneaniline: Trajectory Surface-Hopping Simulations","volume":"117","author":"Cui","year":"2013","journal-title":"J. Phys. Chem. A"},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"121","DOI":"10.1016\/1010-6030(96)04330-4","article-title":"Role of structural flexibility in fluorescence and photochromism of the salicylideneaniline: The \u201caldehyde\u201d ring rotation","volume":"97","author":"Knyazhansky","year":"1996","journal-title":"J. Photochem. Photobiol. A"},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"6329","DOI":"10.1063\/1.481194","article-title":"Photochromism of salicylideneaniline (SA). How the photochromic transient is created: A theoretical approach","volume":"112","author":"Zgierski","year":"2000","journal-title":"J. Chem. Phys."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"9436","DOI":"10.1063\/1.1801991","article-title":"Ultrafast excited-state dynamics in photochromic N-salicylideneaniline studied by femtosecond time-resolved REMPI spectroscopy","volume":"121","author":"Okabe","year":"2004","journal-title":"J. Chem. Phys."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"12760","DOI":"10.1021\/jp103556c","article-title":"Solvent Effects on the Second-Order Nonlinear Optical Responses in the Keto-Enol Equilibrium of a 2-Hydroxy-1-naphthaldehyde Derivative","volume":"114","author":"Bogdan","year":"2010","journal-title":"J. Phys. Chem. C"},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"9554","DOI":"10.1021\/jp9101042","article-title":"Confined Fast and Ultrafast Dynamics of a Photochromic Proton-Transfer Dye within a Zeolite Nanocage","volume":"114","author":"Gil","year":"2010","journal-title":"J. Phys. Chem. C"},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"8217","DOI":"10.1021\/jp412544y","article-title":"Exploring the Photobehavior of Nanocaged Monomers and H- and J-Aggregates of a Proton-Transfer Dye within NaX and NaY Zeolites","volume":"118","author":"Alarcos","year":"2014","journal-title":"J. Phys. Chem. C"},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"145","DOI":"10.1016\/j.cplett.2017.02.024","article-title":"Interrogating ultrafast dynamics of a salicylideneaniline derivative within faujasite zeolites","volume":"683","author":"Alarcos","year":"2017","journal-title":"Chem. Phys. Lett."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"275","DOI":"10.1023\/A:1016031607524","article-title":"The Environmental Effect of MCM-41 Mesoporous Silica on Solid Thermochromic N-(5-Chlorosalicylidene)aniline","volume":"42","author":"Hadjoudis","year":"2002","journal-title":"J. Incl. Phenom. Macrocycl. Chem."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"34","DOI":"10.1016\/j.micromeso.2015.12.037","article-title":"Spectroscopy and relaxation dynamics of salicylideneaniline derivative aggregates encapsulated in MCM41 and SBA15 pores","volume":"226","author":"Alarcos","year":"2016","journal-title":"Micropor. Mesopor. Mat."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"54","DOI":"10.1016\/j.micromeso.2017.04.011","article-title":"Confinement effect on ultrafast events of a salicylideneaniline derivative within mesoporous materials","volume":"248","author":"Alarcos","year":"2017","journal-title":"Microp. Mesopor. Mater."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"475","DOI":"10.1016\/j.jphotochem.2016.09.024","article-title":"Conformational aspects of the photochromic reactivity of two N-salicylidene aniline derivatives in a polymer matrix","volume":"332","author":"Avadanei","year":"2017","journal-title":"J. Photochem. Photobiol. A"},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"7562","DOI":"10.1039\/c3cp54880e","article-title":"Vibrational dynamics of the salicylideneaniline molecule in the solid phase and the confined state","volume":"16","author":"Hureau","year":"2014","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"29","DOI":"10.1016\/S1381-1169(98)00021-1","article-title":"Zeolites as solid solvents","volume":"134","author":"Derouane","year":"1998","journal-title":"J. Mol. Catal. A Chem."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"1706","DOI":"10.1002\/anie.200604336","article-title":"Space- and Time-Resolved Visualization of Acid Catalysis in ZSM-5 Crystals by Fluorescence Microscopy","volume":"46","author":"Roeffaers","year":"2007","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"13586","DOI":"10.1021\/jacs.6b06083","article-title":"Single Molecule Nanospectroscopy Visualizes Proton-Transfer Processes within a Zeolite Crystal","volume":"138","author":"Kubarev","year":"2016","journal-title":"J. Am. Chem. Soc."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"4248","DOI":"10.1021\/acscatal.7b00782","article-title":"Solvent Polarity-Induced Pore Selectivity in H-ZSM-5 Catalysis","volume":"7","author":"Kubarev","year":"2017","journal-title":"ACS Catal."},{"key":"ref_47","unstructured":"Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Barone, V., Mennucci, B., and Petersson, G.A. (2013). Gaussian 09 Revision D.01, Gaussian Inc."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"6615","DOI":"10.1039\/b810189b","article-title":"Long-range corrected hybrid density functionals with damped atom-atom dispersion corrections","volume":"10","author":"Chai","year":"2008","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"15510","DOI":"10.1021\/jp305631q","article-title":"Combined Spectroscopic and Modeling Study of trans-Stilbene Molecule in Cation-Exchanged ZSM-5 Zeolites","volume":"116","author":"Hureau","year":"2012","journal-title":"J. Phys. Chem. C"},{"key":"ref_50","doi-asserted-by":"crossref","unstructured":"Bader, R.F.W. (1990). Atoms in Molecules. A Quantum Theory, Oxford University Press Inc.","DOI":"10.1093\/oso\/9780198551683.001.0001"},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"580","DOI":"10.1002\/jcc.22885","article-title":"Multiwfn: A multifunctional wavefunction analyzer","volume":"33","author":"Lu","year":"2012","journal-title":"J. Comput. Chem."},{"key":"ref_52","doi-asserted-by":"crossref","unstructured":"Wilson, E., Decius, J., and Cross, P. (1955). Molecular Vibrations: The Theory of Infrared and Raman Vibrational Spectra, McGraw-Hill.","DOI":"10.1149\/1.2430134"},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"1393","DOI":"10.1021\/ed083p1393","article-title":"A Pictorial Representation of Normal Modes of Vibration Using Vibrational Symmetry Coordinates","volume":"83","author":"Merlin","year":"2006","journal-title":"J. Chem. Educ."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"79","DOI":"10.1016\/S0006-3495(80)85119-8","article-title":"Resonance Raman studies of the primary photochemical event in visual pigments","volume":"29","author":"Aton","year":"1980","journal-title":"Biophys. J."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"314","DOI":"10.1016\/j.molstruc.2015.09.001","article-title":"Intramolecular hydrogen bonding in N-salicylideneaniline: FT-IR spectrum and quantum chemical calculations","volume":"1102","author":"Dastani","year":"2015","journal-title":"J. Mol. Struct."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"26107","DOI":"10.1039\/C6CP03839E","article-title":"Sorption of 3-hydroxyflavone within channel type zeolites: The effect of confinement on copper(ii) complexation","volume":"18","author":"Moissette","year":"2016","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"4844","DOI":"10.1021\/jp000417r","article-title":"Crystal Structure of Dehydrated CsZSM-5 (5.8Al): Evidence for Nonrandom Aluminum Distribution","volume":"104","author":"Olson","year":"2000","journal-title":"J. Phys. Chem. B"},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"13741","DOI":"10.1021\/jp061909s","article-title":"Hydrated Cs+-Exchanged MFI Zeolites: Location and Population of Cs+ Cations and Water Molecules in Hydrated Cs6.6MFI from In and Ex Situ Powder X-ray Diffraction Data as a Function of Temperature and Other Experimental Conditions","volume":"110","author":"Mentzen","year":"2006","journal-title":"J. Phys. Chem. B"},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"24823","DOI":"10.1021\/jp208246q","article-title":"Framework Sites Preferred by Aluminum in Zeolite ZSM-5. Structure of a Fully Dehydrated, Fully Cs+-Exchanged ZSM-5 Crystal (MFI, Si\/Al = 24)","volume":"115","author":"Kim","year":"2011","journal-title":"J. Phys. Chem. C"},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"3311","DOI":"10.1039\/B304332K","article-title":"Coordination of alkali metal ions in ZSM-5: A combined quantum mechanics\/interatomic potential function study","volume":"5","author":"Kucera","year":"2003","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"93","DOI":"10.1016\/j.molliq.2004.08.001","article-title":"Dielectric relaxation spectroscopy of aqueous amino acid solutions: Dynamics and interactions in aqueous glycine","volume":"117","author":"Sato","year":"2005","journal-title":"J. Mol. Liq."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/24\/4\/795\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T12:34:04Z","timestamp":1760186044000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/24\/4\/795"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2019,2,22]]},"references-count":61,"journal-issue":{"issue":"4","published-online":{"date-parts":[[2019,2]]}},"alternative-id":["molecules24040795"],"URL":"https:\/\/doi.org\/10.3390\/molecules24040795","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2019,2,22]]}}}