{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,30]],"date-time":"2026-09-30T00:24:16Z","timestamp":1790727856858,"version":"4.1.0"},"reference-count":60,"publisher":"MDPI AG","issue":"4","license":[{"start":{"date-parts":[[2016,3,28]],"date-time":"2016-03-28T00:00:00Z","timestamp":1459123200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100003141","name":"Consejo Nacional de Ciencia y Tecnolog\u00eda","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100003141","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>We report single crystal X-ray diffraction (hereafter, SCXRD) analyses of derivatives featuring the electron-donor N-ethylcarbazole or the (4-diphenylamino)phenyl moieties associated with a -CN group attached to a double bond. The compounds are (2Z)-3-(4-(diphenylamino)-phenyl)-2-(pyridin-3-yl)prop-2-enenitrile (I), (2Z)-3-(4-(diphenylamino)phenyl)-2-(pyridin-4-yl)-prop-2-enenitrile (II) and (2Z)-3-(9-ethyl-9H-carbazol-3-yl)-2-(pyridin-2-yl)enenitrile (III). SCXRD analyses reveal that I and III crystallize in the monoclinic space groups P2\/c with Z\u2019 = 2 and C2\/c with Z\u2019 = 1, respectively. Compound II crystallized in the orthorhombic space group Pbcn with Z\u2019 = 1. The molecular packing analysis was conducted to examine the pyridine core effect, depending on the ortho, meta- and para-positions of the nitrogen atom, with respect to the optical properties and number of independent molecules (Z\u2019). It is found that the double bond bearing a diphenylamino moiety introduced properties to exhibit a strong \u03c0-\u03c0-interaction in the solid state. The compounds were examined to evaluate the effects of solvent polarity, the role of the molecular structure, and the molecular interactions on their self-assembly behaviors. Compound I crystallized with a cell with two conformers, anti and syn, due to interaction with solvent. DFT calculations indicated the anti and syn structures of I are energetically stable (less than 1 eV). Also electrochemical and photophysical properties of the compounds were investigated, as well as the determination of optimization calculations in gas and different solvent (chloroform, cyclohexane, methanol, ethanol, tetrahydrofuran, dichloromethane and dimethyl sulfoxide) in the Gaussian09 program. The effect of solvent by PCM method was also investigated. The frontier HOMO and LUMO energies and gap energies are reported.<\/jats:p>","DOI":"10.3390\/molecules21040389","type":"journal-article","created":{"date-parts":[[2016,3,29]],"date-time":"2016-03-29T16:00:28Z","timestamp":1459267228000},"page":"389","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":24,"title":["Conformational and Molecular Structures of \u03b1,\u03b2-Unsaturated Acrylonitrile Derivatives: Photophysical Properties and Their Frontier Orbitals"],"prefix":"10.3390","volume":"21","author":[{"given":"Mar\u00eda","family":"Percino","sequence":"first","affiliation":[{"name":"Laboratorio de Pol\u00edmeros, Centro de Qu\u00edmica, Instituto de Ciencias, Benem\u00e9rita Universidad Aut\u00f3noma de Puebla (BUAP), Complejo de Ciencias, ICUAP, Edif. 103H, 22 Sur y San Claudio, C.P. 72570 Puebla, Puebla, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Margarita","family":"Cer\u00f3n","sequence":"additional","affiliation":[{"name":"Laboratorio de Pol\u00edmeros, Centro de Qu\u00edmica, Instituto de Ciencias, Benem\u00e9rita Universidad Aut\u00f3noma de Puebla (BUAP), Complejo de Ciencias, ICUAP, Edif. 103H, 22 Sur y San Claudio, C.P. 72570 Puebla, Puebla, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Oscar","family":"Rodr\u00edguez","sequence":"additional","affiliation":[{"name":"Laboratorio de Pol\u00edmeros, Centro de Qu\u00edmica, Instituto de Ciencias, Benem\u00e9rita Universidad Aut\u00f3noma de Puebla (BUAP), Complejo de Ciencias, ICUAP, Edif. 103H, 22 Sur y San Claudio, C.P. 72570 Puebla, Puebla, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Guillermo","family":"Soriano-Moro","sequence":"additional","affiliation":[{"name":"Laboratorio de Pol\u00edmeros, Centro de Qu\u00edmica, Instituto de Ciencias, Benem\u00e9rita Universidad Aut\u00f3noma de Puebla (BUAP), Complejo de Ciencias, ICUAP, Edif. 103H, 22 Sur y San Claudio, C.P. 72570 Puebla, Puebla, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mar\u00eda","family":"Castro","sequence":"additional","affiliation":[{"name":"Laboratorio de Pol\u00edmeros, Centro de Qu\u00edmica, Instituto de Ciencias, Benem\u00e9rita Universidad Aut\u00f3noma de Puebla (BUAP), Complejo de Ciencias, ICUAP, Edif. 103H, 22 Sur y San Claudio, C.P. 72570 Puebla, Puebla, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"V\u00edctor","family":"Chapela","sequence":"additional","affiliation":[{"name":"Laboratorio de Pol\u00edmeros, Centro de Qu\u00edmica, Instituto de Ciencias, Benem\u00e9rita Universidad Aut\u00f3noma de Puebla (BUAP), Complejo de Ciencias, ICUAP, Edif. 103H, 22 Sur y San Claudio, C.P. 72570 Puebla, Puebla, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Maxime","family":"Siegler","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Johns Hopkins University, New Chemistry Building, 3400 N. Charles St. Baltimore, MD 21218, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Enrique","family":"P\u00e9rez-Guti\u00e9rrez","sequence":"additional","affiliation":[{"name":"Centro de Investigaciones en \u00d3ptica (CIO), Loma del Bosque 115, Lomas del Campestre, Le\u00f3n, Guanajuato 37000, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2016,3,28]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"2250","DOI":"10.1364\/JOSAB.19.002250","article-title":"Poly(p-phenylenevinylene) derivatives: New promising materials for nonlinear all-optical waveguide switching","volume":"19","author":"Bader","year":"2002","journal-title":"J. Opt. Soc. Am. B"},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"6232","DOI":"10.1039\/c0cc01195a","article-title":"The growing world of crystal forms","volume":"46","author":"Braga","year":"2010","journal-title":"Chem. Commun."},{"key":"ref_3","doi-asserted-by":"crossref","unstructured":"Schwoerer, M., and Wolf, H.C. (2007). Organic Molecular Solids, Wiley-VCH Verlag GmbH & Co.","DOI":"10.1002\/9783527618651"},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"1053","DOI":"10.1002\/1521-4095(200107)13:14<1053::AID-ADMA1053>3.0.CO;2-7","article-title":"Interchain interactions in organic \u03c0-conjugated materials: Impact on electronic structure, optical response, and charge transport","volume":"13","author":"Cornil","year":"2001","journal-title":"Adv. Mater."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"1305","DOI":"10.1039\/b605478a","article-title":"Dipolar interactions and hydrogen bonding in supramolecular aggregates: Understanding cooperative phenomena for 1st hyperpolarizability","volume":"35","author":"Datta","year":"2006","journal-title":"Chem. Soc. Rev."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"42","DOI":"10.1039\/b103508h","article-title":"Photo and electroluminescence of 2-anilino-5-phenylpenta-2,4-dienenitrile derivatives","volume":"12","author":"Chow","year":"2002","journal-title":"J. Mater. Chem."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"818","DOI":"10.1002\/adma.200304770","article-title":"Absorption and emission in quaterthienyl thin films","volume":"15","author":"Sun","year":"2003","journal-title":"Adv. Mater."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"7783","DOI":"10.1002\/anie.200501781","article-title":"Molecular mechanism of the solid-state fluorescence behavior of the organic pigment yellow 101 and its derivatives","volume":"44","author":"Dreuw","year":"2005","journal-title":"Angew. Chem. Int. Ed"},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"478","DOI":"10.1002\/anie.198904781","article-title":"The influence of packing effects on the solid-state fluorescence of diketopyrrolopyrroles","volume":"28","author":"Langhals","year":"1989","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"2168","DOI":"10.1002\/cphc.200600336","article-title":"Cooperative interactions in supramolecular aggregates: Linear and nonlinear responses in calix[4]arenes","volume":"7","author":"Datta","year":"2006","journal-title":"Chem. Phys. Chem."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"1030","DOI":"10.1038\/35082528","article-title":"Control of conformational and interpolymer effects in conjugated polymers","volume":"411","author":"Kim","year":"2001","journal-title":"Nature"},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"765","DOI":"10.1126\/science.265.5173.765","article-title":"Excimers and exciplexes of conjugated polymers","volume":"265","author":"Jenekhe","year":"1994","journal-title":"Science"},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"14152","DOI":"10.1021\/ja054661d","article-title":"Cross dipole stacking in the crystal of distyrylbenzene derivative:\u2009The approach toward high solid-state luminescence efficiency","volume":"127","author":"Xie","year":"2005","journal-title":"J. Am. Chem. Soc."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"2126","DOI":"10.1039\/b517687e","article-title":"A novel strategy for fluorescence enhancement in the solid-state: Affording rigidity to fluorophores packing","volume":"20","author":"Mizobe","year":"2006","journal-title":"Chem. Commun."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"8342","DOI":"10.1002\/anie.200700534","article-title":"Crystal Engineering: A holistic view","volume":"46","author":"Desiraju","year":"2007","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"529","DOI":"10.1021\/ar900228v","article-title":"Micro- and nanocrystals of organic semiconductors","volume":"43","author":"Li","year":"2010","journal-title":"Acc. Chem. Res."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"740","DOI":"10.1002\/anie.200904215","article-title":"A crystal-engineered hydrogen-bonded octachloroperylene diimide with a twisted core: An n-channel organic semiconductor","volume":"49","author":"Gsanger","year":"2010","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"464","DOI":"10.1002\/chem.200902675","article-title":"A Cruciform 6,6\u2032-dipentacenyl: Synthesis, solid-state packing and applications in thin-film transistors","volume":"16","author":"Zhang","year":"2010","journal-title":"Chem. Eur. J."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"4318","DOI":"10.1021\/ja0397916","article-title":"Solid-state packing of conjugated oligomers:\u2009 From \u03c0-stacks to the herringbone structure","volume":"126","author":"Curtis","year":"2004","journal-title":"J. Am. Chem. Soc."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"4155","DOI":"10.1021\/cg100863q","article-title":"Dibenzothiophene Derivatives: From Herringbone to Lamellar Packing Motif","volume":"10","author":"Wang","year":"2010","journal-title":"Cryst. Growth Des."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"6323","DOI":"10.1021\/ja0211499","article-title":"Modeling the polymorphism of pentacene","volume":"125","author":"Mattheus","year":"2003","journal-title":"J. Am. Chem. Soc."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"15322","DOI":"10.1021\/ja045208p","article-title":"Synthesis, Crystal Structure, and Transistor Performance of Tetracene Derivatives","volume":"126","author":"Moon","year":"2004","journal-title":"J. Am. Chem. Soc."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"1644","DOI":"10.1126\/science.1094196","article-title":"Elastomeric transistor stamps: Reversible probing of charge transport in organic crystals","volume":"303","author":"Sundar","year":"2004","journal-title":"Science"},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"7177","DOI":"10.1002\/chem.200700267","article-title":"Synthesis, X-ray diffraction and computational study of the crystal packing of polycyclic hydrocarbons featuring aromatic and perfluoroaromatic rings condensed in the same molecule: 1,2,3,4-Tetrafluoronaphthalene, -anthracene and -phenanthrene","volume":"13","author":"Cozzi","year":"2007","journal-title":"Chem. Eur. J."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"9482","DOI":"10.1021\/ja0162459","article-title":"Functionalized pentacene:\u2009 Improved electronic properties from control of solid-state order","volume":"123","author":"Anthony","year":"2001","journal-title":"J. Am. Chem. Soc."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"926","DOI":"10.1021\/cr050140x","article-title":"Charge transport in organic semiconductors","volume":"107","author":"Coropceanu","year":"2007","journal-title":"Chem. Rev."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"9882","DOI":"10.1021\/ja061827h","article-title":"Effect of Electronic Polarization on Charge-Transport Parameters in Molecular Organic Semiconductors","volume":"128","author":"Valeev","year":"2006","journal-title":"J. Am. Chem. Soc."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"238","DOI":"10.1016\/j.molstruc.2012.10.025","article-title":"Fluorescence improvement of pyridylacrylonitrile by dimethylaminophenyl-substitutions: The effect of packing modes of conjugated compounds","volume":"1034","author":"Percino","year":"2013","journal-title":"J. Mol. Struct."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"8591","DOI":"10.1039\/C4CE00327F","article-title":"The effect of the supramolecular network of (Z)-3-(4-(diphenylamino)phenyl)-2-(pyridin-2-yl)-acrylonitrile on the fluorescence behavior of a single crystal: Experimental and theoretical studies","volume":"16","author":"Percino","year":"2014","journal-title":"CrystEngComm"},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"137","DOI":"10.2174\/1877946803666131213231346","article-title":"Molecular packing and solid-state fluorescence of conjugated compounds of carbazole-acrylonitrile derivatives","volume":"4","author":"Percino","year":"2014","journal-title":"Curr. Phys. Chem."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"74","DOI":"10.1016\/j.molstruc.2014.04.088","article-title":"Important role of molecular packing and intermolecular interactions in two polymorphs of (Z)-2-phenyl-3-(4-(pyridin-2-yl)phenyl)acrylonitrile. Preparation, structures, and optical propertie","volume":"1078","author":"Percino","year":"2014","journal-title":"J. Mol. Struct."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"536","DOI":"10.1039\/c1cs15113d","article-title":"Aggregation-induced emission","volume":"40","author":"Hong","year":"2011","journal-title":"Chem. Soc. Rev."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"14401","DOI":"10.1021\/ja0269082","article-title":"Enhanced emission and its switching in fluorescent organic nanoparticles","volume":"124","author":"An","year":"2002","journal-title":"J. Am. Chem. Soc."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"905","DOI":"10.1002\/adfm.200801278","article-title":"Functionalized siloles: Versatile synthesis, aggregation-induced emission, and sensory and device applications","volume":"19","author":"Li","year":"2009","journal-title":"Adv. Funct. Mater."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"1788","DOI":"10.1039\/C0JM02824J","article-title":"Synthesis and properties of novel aggregation-induced emission compounds with combined tetraphenylethylene and dicarbazolyl triphenylethylene moieties","volume":"21","author":"Zhang","year":"2011","journal-title":"J. Mater. Chem."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"7711","DOI":"10.1039\/c2cc33218c","article-title":"Utilising tetraphenylethene as a dual activator for intramolecular charge transfer and aggregation induced emission","volume":"48","author":"Zhang","year":"2012","journal-title":"Chem. Commun."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"11285","DOI":"10.1021\/jp401440s","article-title":"High-contrast on\/off fluorescence switching via reversible E\u2013Z isomerization of diphenylstilbene containing the \u03b1-cyanostilbenic moiety","volume":"117","author":"Chung","year":"2013","journal-title":"J. Phys. Chem. C"},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"5736","DOI":"10.1039\/C4NJ01103A","article-title":"\u03b1-Cyanostilbene based fluorophores: Aggregation-induced enhanced emission, solvatochromism and the pH effect","volume":"38","author":"Palakollu","year":"2014","journal-title":"New J. Chem."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"5804","DOI":"10.1073\/pnas.092143399","article-title":"Organic semiconductors: A theoretical characterization of the basic parameters governing charge transport","volume":"99","author":"Bredas","year":"2002","journal-title":"Proc. Natl. Acad. Sci. USA"},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"9684","DOI":"10.1021\/ja00100a038","article-title":"A theoretical study of crystallochromy. Quantum interference effects in the spectra of perylene pigments","volume":"116","author":"Kazmaier","year":"1994","journal-title":"J. Am. Chem. Soc."},{"key":"ref_41","doi-asserted-by":"crossref","unstructured":"Wurthner, F. (2004). Perylene bisimide dyes as versatile building blocks for functional supramolecular architectures. Chem. Commun., 1564\u20131579.","DOI":"10.1039\/B401630K"},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"2890","DOI":"10.1021\/cg9002143","article-title":"Multiple Molecules in the Asymmetric Unit (Z\u2032 > 1) and the Formation of False Conglomerate Crystal Structures","volume":"9","author":"Bishop","year":"2009","journal-title":"Cryst. Growth Des."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"1197","DOI":"10.1039\/b514815d","article-title":"Solid state fluorescence of Pigment Yellow 101 and derivatives: A conserved property of the individual molecules","volume":"8","author":"Drew","year":"2006","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"2895","DOI":"10.1021\/cr500564z","article-title":"Packing problems: High Z' crystal structures and their relationship to cocrystals, inclusion compounds, and polymorphism","volume":"115","author":"Steed","year":"2015","journal-title":"Chem. Rev."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"49","DOI":"10.1002\/1521-3773(20020104)41:1<48::AID-ANIE48>3.0.CO;2-U","article-title":"The hydrogen bond in the solid state","volume":"41","author":"Steiner","year":"2002","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"339","DOI":"10.1107\/S0021889808042726","article-title":"OLEX2: A complete structure solution, refinement and analysis program","volume":"42","author":"Dolomanov","year":"2009","journal-title":"J. Appl. Crystallogr."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"4211","DOI":"10.1039\/c1ce05161j","article-title":"Face-to-face \u03c0-stacking in the multicomponent crystals of chloranilic acid, alkali hydrogenchloranilates, and water","volume":"13","year":"2011","journal-title":"CrystEngComm"},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"2206","DOI":"10.1021\/ja9735968","article-title":"A highly \u03c0-stacked organic semiconductor for thin film transistors based on fused thiophenes","volume":"120","author":"Li","year":"1998","journal-title":"J. Am. Chem. Soc."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"10502","DOI":"10.1021\/ja053326m","article-title":"Synthesis and structure of fused \u03b1-oligothiophenes with up to seven rings","volume":"127","author":"Zhang","year":"2005","journal-title":"J. Am. Chem. Soc."},{"key":"ref_50","unstructured":"Mercury 3.5.1. Available online: http:\/\/www.ccdc.cam.ac.uk\/mercury\/."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"8946","DOI":"10.1039\/C4CE01278J","article-title":"C\u2013H\u22efH\u2013C and C\u2013H\u22ef\u03c0 contacts aid transformation of dimeric to monomeric anthracene in the solid state","volume":"16","author":"Nagarajan","year":"2014","journal-title":"CrystEngComm"},{"key":"ref_52","first-page":"181","article-title":"Synthesis and characterization of conjugated pyridine-(N-diphenylamino) acrylonitrile derivatives: Photophysical properties","volume":"1","author":"Percino","year":"2012","journal-title":"J. Mater. Res."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"1573","DOI":"10.1021\/la103894x","article-title":"Carbazole-based cyano-stilbene highly fluorescent microcrystals","volume":"27","author":"Upamali","year":"2011","journal-title":"Langmuir"},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"551","DOI":"10.1002\/adma.19950070608","article-title":"Efficient two layer leds on a polymer blend basis","volume":"7","author":"Pomrnerehne","year":"1995","journal-title":"Adv. Mater."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"3226","DOI":"10.1002\/anie.200500164","article-title":"Solvent Effect on Crystal Polymorphism: Why Addition of Methanol or Ethanol to Aqueous Solutions Induces the Precipitation of the Least Stable Beta Form of Glycine","volume":"44","author":"Weissbuch","year":"2005","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"281","DOI":"10.1002\/ceat.200500375","article-title":"Factor affecting the polymorphic outcome of gycine crystals constrained on patterned substrates","volume":"29","author":"Lee","year":"2006","journal-title":"Chem. Eng. Technol."},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"1035","DOI":"10.1039\/a706669d","article-title":"Crystal Chemistry and Solvent Effects in Polymorphic Systems Sulfathiazole","volume":"94","author":"Blagden","year":"1998","journal-title":"J. Chem. Soc. Faraday Trans."},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"151","DOI":"10.1016\/j.jcrysgro.2012.08.032","article-title":"Role of Kinetic Process in the Solvent Effect on Crystallization of BPT Propyl Ester Polymorph","volume":"373","author":"Kitamura","year":"2013","journal-title":"J. Cryst. Growth"},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"42","DOI":"10.2478\/s11696-010-0075-x","article-title":"Synthesis, optical, and spectroscopic characterisation of substituted 3-phenyl-2-arylacrylonitriles","volume":"65","author":"Percino","year":"2011","journal-title":"Chem. Pap."},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"112","DOI":"10.1107\/S0108767307043930","article-title":"A short history of SHELX","volume":"A64","author":"Sheldrick","year":"2008","journal-title":"Acta Crystallogr."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/21\/4\/389\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T19:21:24Z","timestamp":1760210484000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/21\/4\/389"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2016,3,28]]},"references-count":60,"journal-issue":{"issue":"4","published-online":{"date-parts":[[2016,4]]}},"alternative-id":["molecules21040389"],"URL":"https:\/\/doi.org\/10.3390\/molecules21040389","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2016,3,28]]}}}