{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,4,11]],"date-time":"2026-04-11T17:47:18Z","timestamp":1775929638798,"version":"3.50.1"},"reference-count":67,"publisher":"MDPI AG","issue":"14","license":[{"start":{"date-parts":[[2022,7,7]],"date-time":"2022-07-07T00:00:00Z","timestamp":1657152000000},"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":["3DMM2O"],"award-info":[{"award-number":["3DMM2O"]}],"id":[{"id":"10.13039\/501100001659","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>A series of C3-symmetric fully substituted benzenes were prepared based on alkyl triamino-benzene-tricarboxylates. Starting with a one step-synthesis, the alkyl triamino-benzene-tricarboxylates were synthesized using the corresponding cyanoacetates. The reactivity of these electronically sophisticated compounds was investigated by the formation of azides, the click reaction of the azides and a Sandmeyer-like reaction. Caused by the low stability of triaminobenzenes, direct N-alkylation was rarely reported. The use of the stable alkyl triamino-benzene-tricarboxylates allowed us total N-alkylation under standard alkylation conditions. The molecular structures of the C3-symmetric structures have been corroborated by an X-ray analysis.<\/jats:p>","DOI":"10.3390\/molecules27144369","type":"journal-article","created":{"date-parts":[[2022,7,7]],"date-time":"2022-07-07T22:11:47Z","timestamp":1657231907000},"page":"4369","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["Functionalized C3-Symmetric Building Blocks\u2014The Chemistry of Triaminotrimesic Acid"],"prefix":"10.3390","volume":"27","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-6140-8574","authenticated-orcid":false,"given":"Lisa","family":"Schmidt","sequence":"first","affiliation":[{"name":"Institute of Organic Chemistry, Karlsruhe Institute of Technology (KIT), Fritz-Haber-Weg 6, 76131 Karlsruhe, Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Danny","family":"Wagner","sequence":"additional","affiliation":[{"name":"Institute of Organic Chemistry, Karlsruhe Institute of Technology (KIT), Fritz-Haber-Weg 6, 76131 Karlsruhe, Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Martin","family":"Nieger","sequence":"additional","affiliation":[{"name":"Department of Chemistry, University of Helsinki, P.O. Box 55 (A. I. Virtasen aukio 1), FIN-00014 Helsinki, Finland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Stefan","family":"Br\u00e4se","sequence":"additional","affiliation":[{"name":"Institute of Organic Chemistry, Karlsruhe Institute of Technology (KIT), Fritz-Haber-Weg 6, 76131 Karlsruhe, Germany"},{"name":"Institute of Biological and Chemical Systems\u2014FMS, Karlsruhe Institute of Technology (KIT), Hermann-Von-Helmholtz-Platz 1, 76344 Leopoldshafen, Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2022,7,7]]},"reference":[{"key":"ref_1","unstructured":"Through this manuscript, we refer to C3-symmetric building blocks: D3-symmetric ones are also included."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"6252","DOI":"10.1021\/jo015522r","article-title":"Five Unique Compounds: Xyloketals from Mangrove Fungus Xylaria sp. from the South China Sea Coast","volume":"66","author":"Lin","year":"2001","journal-title":"J. Org. Chem."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"5504","DOI":"10.1021\/jacs.0c00459","article-title":"A Double-Walled Knotted Cage for Guest-Adaptive Molecular Recognition","volume":"142","author":"Tamura","year":"2020","journal-title":"J. Am. Chem. Soc."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"10586","DOI":"10.1021\/ja036540o","article-title":"Complementary C3-Symmetric Donor\u2013Acceptor Components:\u2009 Cocrystal Structure and Control of Mesophase Stability","volume":"125","author":"Park","year":"2003","journal-title":"J. Am. Chem. Soc."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"43","DOI":"10.1016\/S1527-4640(99)80004-7","article-title":"Structures of benzene derivatives with symmetrical substitution by three donor and three acceptor groups","volume":"7","author":"Wolff","year":"1999","journal-title":"Adv. Strained Interesting Org. Mol."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"2739","DOI":"10.1246\/bcsj.61.2739","article-title":"New mesomorphic compounds: N,N\u2032,N\u2033-trialkanoyl-2,4,6-trimethyl-1,3,5-benzenetriamines","volume":"61","author":"Harada","year":"1988","journal-title":"Bull. Chem. Soc. Jpn."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"1292","DOI":"10.1002\/(SICI)1521-4095(199910)11:15<1292::AID-ADMA1292>3.0.CO;2-Z","article-title":"Columnar liquid crystals with highly polar groups. Evaluation of the nonlinear optical properties","volume":"11","author":"Omenat","year":"1999","journal-title":"Adv. Mater."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"8264","DOI":"10.1021\/ja034783a","article-title":"Synthesis, Self-Assembly, and Switching of One-Dimensional Nanostructures from New Crowded Aromatics","volume":"125","author":"Bushey","year":"2003","journal-title":"J. Am. Chem. Soc."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"769","DOI":"10.1021\/acscentsci.7b00183","article-title":"Highly Efficient Thermally Activated Delayed Fluorescence from an Excited-State Intramolecular Proton Transfer System","volume":"3","author":"Mamada","year":"2017","journal-title":"ACS Cent. Sci."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"3305","DOI":"10.1021\/acs.jpclett.0c00498","article-title":"Excited State Dynamics of Thermally Activated Delayed Fluorescence from an Excited State Intramolecular Proton Transfer System","volume":"11","author":"Long","year":"2020","journal-title":"J. Phys. Chem. Lett."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"98","DOI":"10.1039\/C9TC05299B","article-title":"Theoretical perspective for luminescent mechanism of thermally activated delayed fluorescence emitter with excited-state intramolecular proton transfer","volume":"8","author":"Jiang","year":"2020","journal-title":"J. Mater. Chem. C"},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"1259","DOI":"10.1016\/j.cclet.2009.04.030","article-title":"Highly stable supramolecular hydrogels formed from 1,3,5-benzenetricarboxylic acid and hydroxyl pyridines","volume":"20","author":"Tang","year":"2009","journal-title":"Chin. Chem. Lett."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"523","DOI":"10.1038\/nature02311","article-title":"A route to high surface area, porosity and inclusion of large molecules in crystals","volume":"427","author":"Chae","year":"2004","journal-title":"Nature"},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"12987","DOI":"10.1021\/jacs.0c03409","article-title":"2D-Covalent Organic Frameworks with Interlayer Hydrogen Bonding Oriented through Designed Nonplanarity","volume":"142","author":"Alahakoon","year":"2020","journal-title":"J. Am. Chem. Soc."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"11618","DOI":"10.1021\/jacs.8b08282","article-title":"Benzotrithiophene-Based Covalent Organic Frameworks: Construction and Structure Transformation under Ionothermal Condition","volume":"140","author":"Wei","year":"2018","journal-title":"J. Am. Chem. Soc."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"6270","DOI":"10.1002\/anie.201511877","article-title":"Benzotrithiophene-Based Hole-Transporting Materials for 18.2% Perovskite Solar Cells","volume":"55","author":"Zimmermann","year":"2016","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"1436","DOI":"10.1002\/(SICI)1521-3773(20000417)39:8<1436::AID-ANIE1436>3.0.CO;2-U","article-title":"Optimized two-dimensional NLO chromophores with a threefold symmetry axis","volume":"39","author":"Wolff","year":"2000","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"440","DOI":"10.1016\/0009-2614(90)80135-Z","article-title":"Second-harmonic generation from nondipolar noncentrosymmetric aromatic charge-transfer molecules","volume":"172","author":"Ledoux","year":"1990","journal-title":"Chem. Phys. Lett."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"1438","DOI":"10.1021\/cm000816z","article-title":"Octupolar Crystals for Nonlinear Optics: 1,3,5-Trinitro-2,4,6-tris(styryl)benzene Derivatives","volume":"13","author":"Cho","year":"2001","journal-title":"Chem. Mater."},{"key":"ref_20","doi-asserted-by":"crossref","unstructured":"Sukul, P.K., Das, P., Dhakar, G.L., Das, L., and Malik, S. (2022). Effect of Tricarboxylic Acids on the Formation of Hydrogels with Melem or Melamine: Morphological, Structural and Rheological Investigations. Gels, 8.","DOI":"10.3390\/gels8010051"},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"1902","DOI":"10.1039\/C2RA22988A","article-title":"Removal of toxic dyes from aqueous medium using adenine based bicomponent hydrogel","volume":"3","author":"Sukul","year":"2013","journal-title":"RSC Adv."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"17096","DOI":"10.1021\/acs.inorgchem.0c02366","article-title":"Multinuclear 2-(Quinolin-2-yl)quinoxaline-Coordinated Iridium(III) Complexes Tethered by Carbazole Derivatives: Synthesis and Photophysics","volume":"59","author":"Zhu","year":"2020","journal-title":"Inorg. Chem."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"2528","DOI":"10.1021\/jacs.6b00039","article-title":"Dopant-Free Hole-Transporting Material with a C3h Symmetrical Truxene Core for Highly Efficient Perovskite Solar Cells","volume":"138","author":"Huang","year":"2016","journal-title":"J. Am. Chem. Soc."},{"key":"ref_24","unstructured":"Truxene after Trujillo Coke. Truxillense (Trujillo or Peruvian leaf) which is the variety used to flavor beverages such as Coca Cola. The names stems from \u201cTurris Iulia\u201d, the old name fro Trujillo."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"1746","DOI":"10.1002\/adfm.200900093","article-title":"One-dimensional microwires formed by the co-assembly of complementary aromatic donors and acceptors","volume":"19","author":"Wang","year":"2009","journal-title":"Adv. Funct. Mater."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"11314","DOI":"10.1021\/ja073466r","article-title":"Three-dimensional architectures for highly stable pure blue emission","volume":"129","author":"Luo","year":"2007","journal-title":"J. Am. Chem. Soc."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"14560","DOI":"10.1002\/chem.202002826","article-title":"An Isosteric Triaza Analogue of a Polycyclic Aromatic Hydrocarbon Monkey Saddle","volume":"26","author":"Kirschbaum","year":"2020","journal-title":"Chem. A Eur. J."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"53426","DOI":"10.1039\/C5RA06876B","article-title":"Rational design of triazatruxene-based hole conductors for perovskite solar cells","volume":"5","author":"Ramos","year":"2015","journal-title":"RSC Adv."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"5235","DOI":"10.1039\/C8TC04231D","article-title":"Low cost triazatruxene hole transporting material for >20% efficiency perovskite solar cells","volume":"7","author":"Connell","year":"2019","journal-title":"J. Mater. Chem. C"},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"540","DOI":"10.1038\/s41566-019-0415-5","article-title":"Highly efficient blue thermally activated delayed fluorescence emitters based on symmetrical and rigid oxygen-bridged boron acceptors","volume":"13","author":"Ahn","year":"2019","journal-title":"Nat. Photonics"},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"265","DOI":"10.1002\/adfm.200700224","article-title":"Kinked star-shaped fluorene\/triazatruxene co-oligomer hybrids with enhanced functional properties for high-performance, solution-processed, blue organic light-emitting diodes","volume":"18","author":"Lai","year":"2008","journal-title":"Adv. Funct. Mater."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"8738","DOI":"10.1021\/ja303448r","article-title":"Conjugated Microporous Polymers as Molecular Sensing Devices: Microporous Architecture Enables Rapid Response and Enhances Sensitivity in Fluorescence-On and Fluorescence-Off Sensing","volume":"134","author":"Liu","year":"2012","journal-title":"J. Am. Chem. Soc."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"16172","DOI":"10.1021\/jacs.5b11076","article-title":"Triazatruxene-Based Hole Transporting Materials for Highly Efficient Perovskite Solar Cells","volume":"137","author":"Rakstys","year":"2015","journal-title":"J. Am. Chem. Soc."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"24874","DOI":"10.1021\/acs.jpcc.0c08044","article-title":"Coplanar versus Noncoplanar Carboxyl Groups: The Influence of Sterically Enforced Noncoplanarity on the 2D Mixing Behavior of Benzene Tricarboxylic Acids","volume":"124","author":"Reynaerts","year":"2020","journal-title":"J. Phys. Chem. C"},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"11101","DOI":"10.1002\/chem.201402559","article-title":"Ruthenium-Catalyzed Cycloadditions of 1-Haloalkynes with Nitrile Oxides and Organic Azides: Synthesis of 4-Haloisoxazoles and 5-Halotriazoles","volume":"20","author":"Oakdale","year":"2014","journal-title":"Chem. Eur. J."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"1586","DOI":"10.1002\/jlac.198119810908","article-title":"Mono-, bis- and trishydrazo, and -azo compounds in the tricyanobenzene series. I. Preparation and properties of the title compounds","volume":"12","author":"Rieser","year":"1981","journal-title":"Liebigs Ann. Chem."},{"key":"ref_37","unstructured":"Stoessel, P., Buesing, A., Breuning, E., Pflumm, C., Parham, A.H., Eberle, T., and Mujica-Fernaud, T. (2012). Heteroaromatic Compounds for Organic Electroluminescent Devices. (2012095143A1), WO."},{"key":"ref_38","first-page":"483","article-title":"Copper(II) in organic synthesis. IX. The copper(II)-catalyzed Michael reaction as a route to polysubstituted benzene derivatives","volume":"121","author":"Desimoni","year":"1991","journal-title":"Gazz. Chim. Ital."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"1753","DOI":"10.1039\/jr9490001753","article-title":"The preparation of symmetrical aromatic triamines and triisocyanates","volume":"374","author":"Gill","year":"1949","journal-title":"J. Chem. Soc."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"7238","DOI":"10.1021\/jo9010848","article-title":"Molecular Structure and Magnetic Parameters of Septet 2,4,6-Trinitrenotoluene","volume":"74","author":"Chapyshev","year":"2009","journal-title":"J. Org. Chem."},{"key":"ref_41","unstructured":"Breslow, D.S., and Marcantonio, A.F. (1967). Polyazide Crosslinking Agents. (3297674), US."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"6835","DOI":"10.1021\/jp404484q","article-title":"Accurate Prediction of Enthalpies of Formation of Organic Azides by Combining G4 Theory Calculations with an Isodesmic Reaction Scheme","volume":"117","author":"Dorofeeva","year":"2013","journal-title":"J. Phys. Chem. A"},{"key":"ref_43","first-page":"269","article-title":"Theoretical studies on the nitro and azido derivatives of benzene","volume":"69","author":"Du","year":"2011","journal-title":"Huaxue Xuebao"},{"key":"ref_44","first-page":"110","article-title":"Click chemistry approach to graphitic structures","volume":"97","author":"Hoogboom","year":"2007","journal-title":"PMSE Prepr."},{"key":"ref_45","unstructured":"Kim, H.J., and Lee, W.S. (2007). Anion Receptor Comprising Aromatic Amines Substituted with Electron Withdrawing Groups and Electrolyte Using the Same for Alkali Metal Batteries. (2007126262A1), WO."},{"key":"ref_46","unstructured":"Kugler, T. (2010). Organic Electroluminescent Diode. (GB2462433A)."},{"key":"ref_47","first-page":"1406","article-title":"DFT theoretical study on nitrogen-rich compounds C6H6\u2212n(N3)n(n = 1\u20136)","volume":"30","author":"Liu","year":"2009","journal-title":"Gaodeng Xuexiao Huaxue Xuebao"},{"key":"ref_48","first-page":"754","article-title":"QSPR study on thermodynamic properties of the nitro and azido derivatives of benzene","volume":"32","author":"Liu","year":"2015","journal-title":"Yuanzi Yu Fenzi Wuli Xuebao"},{"key":"ref_49","first-page":"2586","article-title":"Nucleophilic substitution in aromatic compounds with fluorine-containing substituents. X. Reactions of 2,4,6-trichloro- and 2,6-dichloro-3,5-bis[(trifluoromethyl)sulfonyl]nitrobenzenes with nucleophiles","volume":"23","author":"Boiko","year":"1987","journal-title":"Zh. Org. Khim."},{"key":"ref_50","unstructured":"Chapyshev, S.V. (2011). Synthesis of 2,4,6-triazidotoluene for Use as Photoaffinic and Crosslinking Agent. (2430080C2), RU."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"303","DOI":"10.1016\/j.jfluchem.2013.07.009","article-title":"Triazidation of 2,4,6-trifluorobenzenes","volume":"156","author":"Chapyshev","year":"2013","journal-title":"J. Fluorine Chem."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"2413","DOI":"10.1021\/jp508470m","article-title":"Heavy Atom Effect on Magnetic Anisotropy of Matrix-Isolated Monobromine Substituted Septet Trinitrene","volume":"119","author":"Misochko","year":"2015","journal-title":"J. Phys. Chem. A"},{"key":"ref_53","unstructured":"Yang, W., Huang, J., Fan, G., Ma, Q., and Qu, Y. (2017). Synthesis Method of Energetic Compound 1-(3,5-dinitro-2,4,6-triaminobenzene)-1,2,4-triazole and Its Derivatives. (106588792A), CN."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"2203","DOI":"10.1039\/C7RA13346D","article-title":"Synthesis, and single crystal structure of fully-substituted polynitrobenzene derivatives for high-energy materials","volume":"8","author":"Yang","year":"2018","journal-title":"RSC Adv."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"10296","DOI":"10.1039\/C8CC05413D","article-title":"A novel method to synthesize stable nitrogen-rich polynitrobenzenes with \u03c0-stacking for high-energy-density energetic materials","volume":"54","author":"Yang","year":"2018","journal-title":"Chem. Commun."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"5188","DOI":"10.1002\/anie.200400657","article-title":"Organic azides. An exploding diversity of a unique class of compounds","volume":"44","author":"Brase","year":"2005","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_57","doi-asserted-by":"crossref","unstructured":"Keicher, T., and Loebbecke, S. (2010). Lab-Scale Synthesis of Azido Compounds: Safety Measures and Analysis, John Wiley & Sons Ltd.","DOI":"10.1002\/9780470682517.ch1"},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"472","DOI":"10.1002\/mrc.4877","article-title":"EPR spectroscopy of multicomponent, multispin molecular system obtained by the photolysis of 2,4,6-triazido-3-cyano-5-fluoropyridine in solid argon","volume":"57","author":"Chapyshev","year":"2019","journal-title":"Magn. Reson. Chem."},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"1258","DOI":"10.1002\/chem.202002234","article-title":"Molecular Magnets: The Synthesis and Characterization of High-Spin Nitrenes","volume":"27","author":"Chapyshev","year":"2021","journal-title":"Chem.-Eur. J."},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"12994","DOI":"10.1002\/anie.201904556","article-title":"Persistent Organic High-Spin Trinitrenes","volume":"58","author":"Chapyshev","year":"2019","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_61","unstructured":"Stoessel, P., Buesing, A., Voges, F., Pflumm, C., Parham, A.H., Eberle, T., and Mujica-Fernaud, T. (2012). Benzene Derivatives with Nitrogen-Containing Substituents for Organic Electronic Devices and Their Preparation and the Devices. (2012143079A1), WO."},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"16250","DOI":"10.1039\/C4TA03154G","article-title":"What can pKa and NBO charges of the ligands tell us about the water and thermal stability of metal organic frameworks?","volume":"2","author":"Lu","year":"2014","journal-title":"J. Mater. Chem. A"},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"3787","DOI":"10.1002\/cber.19681011118","article-title":"Aminobenzole, I.V. N-Persubstituierte 3.5-Diamino-phenole und 1.3.5-Triamino-benzole","volume":"101","author":"Effenberger","year":"1968","journal-title":"Chem. Ber."},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"1403","DOI":"10.1021\/jo001544m","article-title":"Synthesis of 2,3-Dihydroindoles, Indoles, and Anilines by Transition Metal-Free Amination of Aryl Chlorides","volume":"66","author":"Beller","year":"2001","journal-title":"J. Org. Chem."},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"504","DOI":"10.1055\/s-1998-1692","article-title":"Palladium-Catalyzed Multiple Aryl Aminations of Polybromobenzenes","volume":"1998","author":"Witulski","year":"1998","journal-title":"Synlett"},{"key":"ref_66","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1107\/S2053273314026370","article-title":"SHELXT\u2014Integrated space-group and crystal-structure determination","volume":"71","author":"Sheldrick","year":"2015","journal-title":"Acta Crystallogr. Sect. A"},{"key":"ref_67","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1107\/S2053229614024218","article-title":"Crystal structure refinement with SHELXL","volume":"71","author":"Sheldrick","year":"2015","journal-title":"Acta Crystallogr. Sect. C Struct. Chem."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/27\/14\/4369\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T23:44:05Z","timestamp":1760139845000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/27\/14\/4369"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022,7,7]]},"references-count":67,"journal-issue":{"issue":"14","published-online":{"date-parts":[[2022,7]]}},"alternative-id":["molecules27144369"],"URL":"https:\/\/doi.org\/10.3390\/molecules27144369","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2022,7,7]]}}}