The Polymorphism of Orlyum White 520T, an Ultraviolet Luminescent Security Ink
The polymorphism of the ultraviolet luminescent security ink Orlyum White 520T (<i>N</i>-(2-(4-oxo-4<i>H</i>-benzo[d][3,1]-oxazin-2-yl)phenyl)naphthalene-2-sulfonamide) is revealed, obtaining two new polymorphic forms with enhanced stability. Beyond the known form (lit. mp. 1...
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2025-04-01
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| author | János Madarász Nóra V. May Petra Bombicz György Pokol Richárd Kocsis Bálint Hegymegi-Barakonyi Tibor Gizur |
| author_facet | János Madarász Nóra V. May Petra Bombicz György Pokol Richárd Kocsis Bálint Hegymegi-Barakonyi Tibor Gizur |
| author_sort | János Madarász |
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| description | The polymorphism of the ultraviolet luminescent security ink Orlyum White 520T (<i>N</i>-(2-(4-oxo-4<i>H</i>-benzo[d][3,1]-oxazin-2-yl)phenyl)naphthalene-2-sulfonamide) is revealed, obtaining two new polymorphic forms with enhanced stability. Beyond the known form (lit. mp. 184.8–185.2 °C, Form III, YOCTAO), we succeeded in gaining two new polymorphic forms, Form II and Form I, with higher melting points of 195–196 and 197–198 °C, respectively. Their elemental composition, <sup>1</sup>H and <sup>13</sup>C NMR spectra have been found to be identical, while their powder XRD patterns and FT-IR spectra are significantly different. Based on the single-crystal structure determination of Form II and redetermination of Form III, we uncover the similarities and differences in their packing arrangement and in their secondary interaction systems, all of which affect the molecular conformations in their crystals. In order to explain their significantly distinguishable melting points, Hirshfeld surface analysis and lattice energy calculations have also been carried out. We have made efforts toward revealing the reproducible conditions under which certain polymorphs are formed. It seems that the solvents or other probable organic contaminations are more likely responsible for the formation, nucleation and growth of crystals of various polymorphic forms, traced by thermogravimetric evolved gas analysis (TG/DTA-EGA-MS). |
| format | Article |
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| language | English |
| publishDate | 2025-04-01 |
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| series | Molecules |
| spelling | doaj-art-820e148bb11d4b6199515d53feff4b312025-08-20T02:18:20ZengMDPI AGMolecules1420-30492025-04-01308167110.3390/molecules30081671The Polymorphism of Orlyum White 520T, an Ultraviolet Luminescent Security InkJános Madarász0Nóra V. May1Petra Bombicz2György Pokol3Richárd Kocsis4Bálint Hegymegi-Barakonyi5Tibor Gizur6Department of Inorganic and Analytical Chemistry, Budapest University of Technology and Economics, Műegyetem rkp. 3, HU-1111 Budapest, HungaryCentre for Structural Science, HUN-REN Research Centre for Natural Sciences, Magyar Tudósok Körútja 2, HU-1117 Budapest, HungaryCentre for Structural Science, HUN-REN Research Centre for Natural Sciences, Magyar Tudósok Körútja 2, HU-1117 Budapest, HungaryDepartment of Inorganic and Analytical Chemistry, Budapest University of Technology and Economics, Műegyetem rkp. 3, HU-1111 Budapest, HungaryLuminoChem R&D Ltd., Háros utca 7/A, HU-1222 Budapest, HungaryLuminoChem R&D Ltd., Háros utca 7/A, HU-1222 Budapest, HungaryDepartment of Organic Chemistry and Technology, Budapest University of Technology and Economics, Műegyetem rkp. 3, HU-1111 Budapest, HungaryThe polymorphism of the ultraviolet luminescent security ink Orlyum White 520T (<i>N</i>-(2-(4-oxo-4<i>H</i>-benzo[d][3,1]-oxazin-2-yl)phenyl)naphthalene-2-sulfonamide) is revealed, obtaining two new polymorphic forms with enhanced stability. Beyond the known form (lit. mp. 184.8–185.2 °C, Form III, YOCTAO), we succeeded in gaining two new polymorphic forms, Form II and Form I, with higher melting points of 195–196 and 197–198 °C, respectively. Their elemental composition, <sup>1</sup>H and <sup>13</sup>C NMR spectra have been found to be identical, while their powder XRD patterns and FT-IR spectra are significantly different. Based on the single-crystal structure determination of Form II and redetermination of Form III, we uncover the similarities and differences in their packing arrangement and in their secondary interaction systems, all of which affect the molecular conformations in their crystals. In order to explain their significantly distinguishable melting points, Hirshfeld surface analysis and lattice energy calculations have also been carried out. We have made efforts toward revealing the reproducible conditions under which certain polymorphs are formed. It seems that the solvents or other probable organic contaminations are more likely responsible for the formation, nucleation and growth of crystals of various polymorphic forms, traced by thermogravimetric evolved gas analysis (TG/DTA-EGA-MS).https://www.mdpi.com/1420-3049/30/8/1671structure–property relationshipultraviolet (UV) fluorescencesingle-crystal and powder X-ray diffraction (XRD)FT-IR spectroscopydifferential scanning calorimetry (DSC)TG/DTA-MS |
| spellingShingle | János Madarász Nóra V. May Petra Bombicz György Pokol Richárd Kocsis Bálint Hegymegi-Barakonyi Tibor Gizur The Polymorphism of Orlyum White 520T, an Ultraviolet Luminescent Security Ink Molecules structure–property relationship ultraviolet (UV) fluorescence single-crystal and powder X-ray diffraction (XRD) FT-IR spectroscopy differential scanning calorimetry (DSC) TG/DTA-MS |
| title | The Polymorphism of Orlyum White 520T, an Ultraviolet Luminescent Security Ink |
| title_full | The Polymorphism of Orlyum White 520T, an Ultraviolet Luminescent Security Ink |
| title_fullStr | The Polymorphism of Orlyum White 520T, an Ultraviolet Luminescent Security Ink |
| title_full_unstemmed | The Polymorphism of Orlyum White 520T, an Ultraviolet Luminescent Security Ink |
| title_short | The Polymorphism of Orlyum White 520T, an Ultraviolet Luminescent Security Ink |
| title_sort | polymorphism of orlyum white 520t an ultraviolet luminescent security ink |
| topic | structure–property relationship ultraviolet (UV) fluorescence single-crystal and powder X-ray diffraction (XRD) FT-IR spectroscopy differential scanning calorimetry (DSC) TG/DTA-MS |
| url | https://www.mdpi.com/1420-3049/30/8/1671 |
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