{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,23]],"date-time":"2026-03-23T12:51:37Z","timestamp":1774270297009,"version":"3.50.1"},"reference-count":65,"publisher":"MDPI AG","issue":"1","license":[{"start":{"date-parts":[[2023,12,21]],"date-time":"2023-12-21T00:00:00Z","timestamp":1703116800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Funda\u00e7\u00e3o para a Ci\u00eancia e a Tecnologia (FCT), Portugal","award":["UIDB\/00100\/2020"],"award-info":[{"award-number":["UIDB\/00100\/2020"]}]},{"name":"Funda\u00e7\u00e3o para a Ci\u00eancia e a Tecnologia (FCT), Portugal","award":["UIDP\/00100\/2020"],"award-info":[{"award-number":["UIDP\/00100\/2020"]}]},{"name":"Funda\u00e7\u00e3o para a Ci\u00eancia e a Tecnologia (FCT), Portugal","award":["LA\/P\/0056\/2020"],"award-info":[{"award-number":["LA\/P\/0056\/2020"]}]},{"name":"Centro de Qu\u00edmica Estrutural","award":["UIDB\/00100\/2020"],"award-info":[{"award-number":["UIDB\/00100\/2020"]}]},{"name":"Centro de Qu\u00edmica Estrutural","award":["UIDP\/00100\/2020"],"award-info":[{"award-number":["UIDP\/00100\/2020"]}]},{"name":"Centro de Qu\u00edmica Estrutural","award":["LA\/P\/0056\/2020"],"award-info":[{"award-number":["LA\/P\/0056\/2020"]}]},{"name":"Institute of Molecular Sciences","award":["UIDB\/00100\/2020"],"award-info":[{"award-number":["UIDB\/00100\/2020"]}]},{"name":"Institute of Molecular Sciences","award":["UIDP\/00100\/2020"],"award-info":[{"award-number":["UIDP\/00100\/2020"]}]},{"name":"Institute of Molecular Sciences","award":["LA\/P\/0056\/2020"],"award-info":[{"award-number":["LA\/P\/0056\/2020"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Symmetry"],"abstract":"<jats:p>Boron-doped organic compounds display unique properties as a result of the presence of an empty p orbital on boron and the ability to switch between a trigonal planar and a tetrahedral geometry. In recent years, they have found several applications not only as synthetic reagents, e.g., in the Suzuki\u2013Miyaura reaction, but also as pharmaceuticals and as specialized materials due to their optical and electronic properties. Some boron compounds may exist as atropisomers, and these rotamers may have different properties according to their sense of rotation. Synthetic strategies to separate them and, more recently, to obtain them in an asymmetric manner are becoming popular. In this review, we survey the literature on this emerging field of research.<\/jats:p>","DOI":"10.3390\/sym16010011","type":"journal-article","created":{"date-parts":[[2023,12,21]],"date-time":"2023-12-21T03:36:17Z","timestamp":1703129777000},"page":"11","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":6,"title":["Synthesis of Axially Chiral Boron Compounds"],"prefix":"10.3390","volume":"16","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-3101-016X","authenticated-orcid":false,"given":"Ana Maria","family":"Faisca Phillips","sequence":"first","affiliation":[{"name":"Coordination Chemistry and Catalysis Group, Centro de Qu\u00edmica Estrutural, Institute of Molecular Sciences, Instituto Superior T\u00e9cnico, Universidade de Lisboa, Av. Rovisco Pais 1, 1049-001 Lisboa, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8323-888X","authenticated-orcid":false,"given":"Armando J. L.","family":"Pombeiro","sequence":"additional","affiliation":[{"name":"Coordination Chemistry and Catalysis Group, Centro de Qu\u00edmica Estrutural, Institute of Molecular Sciences, Instituto Superior T\u00e9cnico, Universidade de Lisboa, Av. Rovisco Pais 1, 1049-001 Lisboa, Portugal"}]}],"member":"1968","published-online":{"date-parts":[[2023,12,21]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"1275","DOI":"10.4155\/fmc.09.71","article-title":"Therapeutic Potential of Boron-Containing Compounds","volume":"1","author":"Baker","year":"2009","journal-title":"Future Med. Chem."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"13629","DOI":"10.1039\/D1CC05481C","article-title":"The Modern Role of Boron as a \u2018Magic Element\u2019","volume":"57","author":"Chatterjee","year":"2021","journal-title":"Chem. Commun."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"3985","DOI":"10.1021\/cr100026f","article-title":"Advances in the Synthesis of Organoborane Polymers for Optical, Electronic, and Sensory Applications","volume":"110","year":"2010","journal-title":"Chem. Rev."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"7351","DOI":"10.1039\/D2CC02362H","article-title":"Substitution at Boron in BODIPYs","volume":"58","author":"Gapare","year":"2022","journal-title":"Chem. Commun."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"73","DOI":"10.1007\/7081_2017_6","article-title":"Boron-Containing Chiral Auxiliaries","volume":"55","author":"Mantel","year":"2020","journal-title":"Top. Heterocycl. Chem."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"8848","DOI":"10.1039\/C5CS00338E","article-title":"Boron-Selective Reactions as Powerful Tools for Modular Synthesis of Diverse Complex Molecules","volume":"44","author":"Xu","year":"2015","journal-title":"Chem. Soc. Rev."},{"key":"ref_7","unstructured":"Crow, J.M. (Chemistry World, 2019). The fifth element, Chemistry World."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"8","DOI":"10.1139\/v08-110","article-title":"B\u2013N as a C\u2013C Substitute in Aromatic Systems","volume":"87","author":"Bosdet","year":"2009","journal-title":"Can. J. Chem."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"6074","DOI":"10.1002\/anie.201200063","article-title":"Recent Advances in Azaborine Chemistry","volume":"51","author":"Campbell","year":"2012","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"4353","DOI":"10.1002\/ejic.201700562","article-title":"Recent Developments in Azaborinine Chemistry","volume":"2017","author":"Braunschweig","year":"2017","journal-title":"Eur. J. Inorg. Chem."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"1184","DOI":"10.1021\/jacs.7b09446","article-title":"The State of the Art in Azaborine Chemistry: New Synthetic Methods and Applications","volume":"140","author":"Giustra","year":"2018","journal-title":"J. Am. Chem. Soc."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"4381","DOI":"10.1039\/D3CS00163F","article-title":"Stereoselective Formation of Boron-Stereogenic Organoboron Derivatives","volume":"52","author":"Aupic","year":"2023","journal-title":"Chem. Soc. Rev."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"16302","DOI":"10.1021\/jacs.1c08482","article-title":"Catalytic Enantioselective Construction of Chiroptical Boron-Stereogenic Compounds","volume":"143","author":"Zu","year":"2021","journal-title":"J. Am. Chem. Soc."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"1730","DOI":"10.1039\/C6TC05418H","article-title":"Tuning of Electronic Properties via Labile N\u2192B-Coordination in Conjugated Organoboranes","volume":"5","author":"Schraff","year":"2017","journal-title":"J. Mater. Chem. C"},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"3537","DOI":"10.1039\/C9CS00153K","article-title":"Boron-Based Stimuli Responsive Materials","volume":"48","author":"Mellerup","year":"2019","journal-title":"Chem. Soc. Rev."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"1855","DOI":"10.1016\/j.chempr.2022.04.011","article-title":"Atropisomers Beyond the C\u2013C Axial Chirality: Advances in Catalytic Asymmetric Synthesis","volume":"8","author":"Mei","year":"2022","journal-title":"Chem"},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"12924","DOI":"10.1021\/jacs.1c05079","article-title":"Chiral Phosphoric Acid-Catalyzed Remote Control of Axial Chirality at Boron-Carbon Bond","volume":"143","author":"Yang","year":"2021","journal-title":"J. Am. Chem. Soc."},{"key":"ref_18","doi-asserted-by":"crossref","unstructured":"da Silva, E.M., Vidal, H.D.A., Janu\u00e1rio, M.A.P., and Corr\u00eaa, A.G. (2023). Advances in the Asymmetric Synthesis of BINOL Derivatives. Molecules, 28.","DOI":"10.3390\/molecules28010012"},{"key":"ref_19","doi-asserted-by":"crossref","unstructured":"Zhou, Q.L. (2011). Priviledged Chiral Ligands and Catalysts, Wiley-VCH.","DOI":"10.1002\/9783527635207"},{"key":"ref_20","unstructured":"B\u00f6rner, A. (2008). Phosphorus Ligands in Asymmetric Catalysis, Wiley-VCH."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"581","DOI":"10.1021\/ar700137z","article-title":"Chiral Diphosphine and Monodentate Phosphorus Ligands on a Spiro Scaffold for Transition-Metal-Catalyzed Asymmetric Reactions","volume":"41","author":"Xie","year":"2008","journal-title":"Acc. Chem. Res."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"499","DOI":"10.2174\/157017905774322631","article-title":"Ten Years of Research on NOBIN Chemistry","volume":"2","author":"Ding","year":"2005","journal-title":"Curr. Org. Synth."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"9277","DOI":"10.1021\/acs.chemrev.5b00041","article-title":"Stronger Br\u00f8nsted Acids: Recent Progress","volume":"115","author":"Akiyama","year":"2015","journal-title":"Chem. Rev."},{"key":"ref_24","doi-asserted-by":"crossref","unstructured":"Mahmudov, K.T., Kopylovich, M.N., Guedes da Silva, M.F.C., and Pombeiro, A.J.L. (2019). Noncovalent Interactions in Catalysis, Royal Society of Chemistry Publishing.","DOI":"10.1039\/9781788016490"},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"9388","DOI":"10.1021\/acs.chemrev.5b00128","article-title":"Development and Applications of Disulfonimides in Enantioselective Organocatalysis","volume":"115","author":"James","year":"2015","journal-title":"Chem. Rev."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"7485","DOI":"10.1039\/D0OB01742F","article-title":"Chiral Disulfonimides: A Versatile Template for Asymmetric Catalysis","volume":"18","author":"Benda","year":"2020","journal-title":"Org. Biomol. Chem."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"2920","DOI":"10.1021\/acs.accounts.2c00509","article-title":"Organocatalytic Enantioselective Synthesis of Axially Chiral Molecules: Development of Strategies and Skeletons","volume":"55","author":"Cheng","year":"2022","journal-title":"Acc. Chem. Res."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"7005","DOI":"10.1021\/jm200584g","article-title":"Assessing Atropisomer Axial Chirality in Drug Discovery and Development","volume":"54","author":"LaPlante","year":"2011","journal-title":"J. Med. Chem."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"2904","DOI":"10.1021\/acs.accounts.2c00500","article-title":"Atropisomerism in the Pharmaceutically Relevant Realm","volume":"55","author":"Basilaia","year":"2022","journal-title":"Acc. Chem. Res."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"2581","DOI":"10.1021\/acs.accounts.2c00485","article-title":"Atropisomerism in Drug Discovery: A Medicinal Chemistry Perspective Inspired by Atropisomeric Class I PI3K Inhibitors","volume":"55","author":"Perreault","year":"2022","journal-title":"Acc. Chem. Res."},{"key":"ref_31","doi-asserted-by":"crossref","unstructured":"Faisca Phillips, A.M., and Pombeiro, A.J.L. (2023). Atropselective Organocatalytic Synthesis of Chiral Compounds Containing Nitrogen Along the Axis of Chirality. Symmetry, 15.","DOI":"10.3390\/sym15061261"},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"1562","DOI":"10.1039\/C4NP00121D","article-title":"A Twist of Nature\u2014The Significance of Atropisomers in Biological Systems","volume":"32","author":"Smyth","year":"2015","journal-title":"Nat. Prod. Rep."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"4070","DOI":"10.1002\/ejoc.201901918","article-title":"Stereochemistry and Recent Applications of Axially Chiral Organic Molecules","volume":"2020","author":"Mancinelli","year":"2020","journal-title":"Eur. J. Org. Chem."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"e202206631","DOI":"10.1002\/anie.202206631","article-title":"Chemically Driven Rotatory Molecular Machines","volume":"61","author":"Mondal","year":"2022","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1002\/9780470147238.ch1","article-title":"Recent Advances in Atropisomerism","volume":"Volume 14","author":"Allinger","year":"1983","journal-title":"Topics in Stereochemistry"},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"505","DOI":"10.1002\/cmdc.201000485","article-title":"Revealing Atropisomer Axial Chirality in Drug Discovery","volume":"6","author":"LaPlante","year":"2011","journal-title":"ChemMedChem"},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"2692","DOI":"10.1021\/acs.orglett.6b01159","article-title":"Axial Chirality about Boron\u2212Carbon Bond: Atropisomeric Azaborines","volume":"18","author":"Mazzanti","year":"2016","journal-title":"Org. Lett."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"2728","DOI":"10.1039\/jr9590002728","article-title":"546. New Heteroaromatic Compounds. Part III. 2,1-Borazaro-naphthalene (1,2-dihydro-1-aza-2-boranaphthalene)","volume":"1959","author":"Dewar","year":"1959","journal-title":"J. Chem. Soc."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"833","DOI":"10.1007\/s11224-007-9229-z","article-title":"Borazine: To Be or Not To Be Aromatic","volume":"18","author":"Islas","year":"2007","journal-title":"Struct. Chem."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"2769","DOI":"10.1021\/ic50141a047","article-title":"Atropisomerism in Aryl-Substituted Borazines","volume":"13","author":"Johnson","year":"1974","journal-title":"Inorg. Chem."},{"key":"ref_41","first-page":"191","article-title":"Atropisomerism in Boron-Nitrogen Heterocycles","volume":"42b","author":"Seidel","year":"1987","journal-title":"Z2. Naturforsch. Teil B"},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"1447","DOI":"10.1021\/ic00332a035","article-title":"Atropisomerism in o-Aryl-Substituted Borazines","volume":"29","author":"Allaoud","year":"1990","journal-title":"Inorg. Chem."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"301","DOI":"10.1515\/MGMC.1998.21.5.301","article-title":"Synthesis and Characterization of 2,4,6-Tris{[bis(isopropylamino)borylkisopropyl)amino}borazine","volume":"21","author":"Cornu","year":"1998","journal-title":"Main Group Met. Chem."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"15394","DOI":"10.1002\/chem.201202280","article-title":"Boron-Doped Tri(9,10-anthrylene)s: Synthesis, Structural Characterization, and Optoelectronic Properties","volume":"18","author":"Hoffend","year":"2012","journal-title":"Chem"},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"2290","DOI":"10.1002\/adsc.202001356","article-title":"Threat to the Throne: Can Two Cooperating Boron Atoms Rival Transition Metals in Chemical Bond Activation and Catalysis?","volume":"363","author":"Preya","year":"2021","journal-title":"Adv. Synth. Catal."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"3613","DOI":"10.1039\/C9CS00072K","article-title":"Small Molecule Activation by Boron-Containing Heterocycles","volume":"48","author":"Su","year":"2019","journal-title":"Chem. Soc. Rev."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"8231","DOI":"10.1021\/acs.chemrev.8b00561","article-title":"Metallomimetic Chemistry at Boron","volume":"119","author":"Pranckevicius","year":"2019","journal-title":"Chem. Rev."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"13526","DOI":"10.1039\/D1CC05173C","article-title":"Harnessing the Electronic Differences Between CAAC-Stabilised 1,4-Diborabenzene and 9,10-Diboraanthracene for Synthesis","volume":"57","author":"Dietz","year":"2021","journal-title":"Chem. Commun."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"1395","DOI":"10.1021\/ol070328y","article-title":"Blue Fluorescent 4a-Aza-4b-boraphenanthrenes","volume":"9","author":"Bosdet","year":"2007","journal-title":"Org. Lett."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"3117","DOI":"10.1002\/anie.201209706","article-title":"Azaborine Compounds for Organic Field-Effect Transistors: Efficient Synthesis, Remarkable Stability, and BN Dipole Interactions","volume":"52","author":"Wang","year":"2013","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"12253","DOI":"10.1021\/acs.joc.9b01550","article-title":"Axial Chirality at the Boron\u2212Carbon Bond: Synthesis, Stereodynamic Analysis, and Atropisomeric Resolution of 6-Aryl-5,6-dihydrodibenzo[c,e][1,2]azaborinines","volume":"84","author":"Mazzanti","year":"2019","journal-title":"J. Org. Chem."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"10294","DOI":"10.1002\/anie.201102717","article-title":"Synthesis and Reactions of N-Heterocyclic Carbene Boranes","volume":"50","author":"Curran","year":"2011","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"4465","DOI":"10.1021\/acs.joc.5b00324","article-title":"Dynamic Behavior of N-Heterocyclic Carbene Boranes: Boron\u2212Carbene Bonds in B,B-Disubstituted N,N-Dimethylimidazol-2-ylidene Boranes Have Substantial Rotation Barriers","volume":"80","author":"Damodaran","year":"2015","journal-title":"J. Org. Chem."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"3007","DOI":"10.1039\/D0OB00421A","article-title":"Non-biaryl Atropisomerism at the C\u2013B Bond in Sterically Hindered Aminoarylboranes","volume":"18","author":"Birepinte","year":"2020","journal-title":"Org. Biomol. Chem."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"871","DOI":"10.1021\/acs.joc.2c02209","article-title":"Synthesis and Stereodynamic and Emission Properties of Dissymmetric Bis-Aryl Carbazole Boranes and Identification of a CPL-Active B\u2212C Atropisomeric Compound","volume":"88","author":"Pecorari","year":"2023","journal-title":"J. Org. Chem."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"4496","DOI":"10.1039\/D1QO00715G","article-title":"Highly Twisted Carbazole-Borane Derivates: B-N Stereodynamic Analysis and Consequence on their Emission Properties","volume":"8","author":"Pecorari","year":"2021","journal-title":"Org. Chem. Front."},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"2968","DOI":"10.1039\/D0CS00870B","article-title":"Atroposelective transformation of axially chiral (hetero)biaryls. From Desymmetrization to Modern Resolution Strategies","volume":"50","author":"Carmona","year":"2021","journal-title":"Chem. Soc. Rev."},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"4805","DOI":"10.1021\/acs.chemrev.0c01306","article-title":"Recent Advances in Catalytic Asymmetric Construction of Atropisomers","volume":"121","author":"Cheng","year":"2021","journal-title":"Chem. Rev."},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"10048","DOI":"10.1021\/jacs.1c04345","article-title":"Construction of Axially Chiral Arylborons via Atroposelective Miyaura Borylation","volume":"143","author":"Yang","year":"2021","journal-title":"J. Am. Chem. Soc."},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"116124","DOI":"10.1016\/j.poly.2022.116124","article-title":"A Retrospective-Prospective Review of Suzuki\u2013Miyaura Reaction: From Cross-Coupling Reaction to Pharmaceutical Industry Applications","volume":"227","author":"Farhang","year":"2022","journal-title":"Polyhedron"},{"key":"ref_61","doi-asserted-by":"crossref","unstructured":"Pereira, M.M., and Calvete, M.J.F. (2018). Sustainable Synthesis of Pharmaceuticals: Using Transition Metals as Catalysts, Royal Society of Chemistry.","DOI":"10.1039\/9781788010658"},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"4438","DOI":"10.1038\/s41467-023-40164-6","article-title":"Construction of C-B Axial Chirality Via Dynamic Kinetic Asymmetric Cross-Coupling Mediated by Tetracoordinate Boron","volume":"14","author":"Yang","year":"2023","journal-title":"Nat. Commun."},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"12623","DOI":"10.1002\/anie.202002518","article-title":"Enantioselective Synthesis of Atropisomerswith Multiple Stereogenic Axes","volume":"59","author":"Bao","year":"2020","journal-title":"Angew.Chem. Int. Ed."},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"e202210456","DOI":"10.1002\/anie.202210456","article-title":"Stepwise Asymmetric Allylic Substitution-Isomerization Enabled Mimetic Synthesis of Axially Chiral B,N-Heterocycles","volume":"61","author":"Zhang","year":"2022","journal-title":"Ang. Chem. Int. Ed."},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"101005","DOI":"10.1016\/j.xcrp.2022.101005","article-title":"Asymmetric Allylic Substitution-Isomerization for Accessing Axially Chiral Vinylindoles bby Intramolecular \u03c0-\u03c0 Stacking Interactions","volume":"3","author":"Wu","year":"2022","journal-title":"Cell Rep. Phys. Sci."}],"container-title":["Symmetry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/2073-8994\/16\/1\/11\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T21:39:19Z","timestamp":1760132359000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/2073-8994\/16\/1\/11"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,12,21]]},"references-count":65,"journal-issue":{"issue":"1","published-online":{"date-parts":[[2024,1]]}},"alternative-id":["sym16010011"],"URL":"https:\/\/doi.org\/10.3390\/sym16010011","relation":{},"ISSN":["2073-8994"],"issn-type":[{"value":"2073-8994","type":"electronic"}],"subject":[],"published":{"date-parts":[[2023,12,21]]}}}