Comparing the crystal structures and spectroscopic properties of a p-hydroxy styrylquinolinium dye with those of its p-dimethylamino analogue
Two previously synthesized styrylquinolinium dyes, namely (E)-1-butyl-4-(4-(dimethylamino)styryl)quinolinium iodide (D36) and (E)-1-butyl-4-(4-hydroxystyryl)quinolinium iodide (D34), were compared in terms of their properties by single-crystal X-ray diffraction (XRD), Hirshfeld surface analysis, Fou...
| Main Authors: | , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Elsevier
2024-04-01
|
| Series: | Heliyon |
| Subjects: | |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S2405844024053465 |
| _version_ | 1797199855848783872 |
|---|---|
| author | Mina Todorova Rüdiger W. Seidel Mihaela Stoyanova Tsonko M. Kolev Rumyana Bakalska |
| author_facet | Mina Todorova Rüdiger W. Seidel Mihaela Stoyanova Tsonko M. Kolev Rumyana Bakalska |
| author_sort | Mina Todorova |
| collection | DOAJ |
| description | Two previously synthesized styrylquinolinium dyes, namely (E)-1-butyl-4-(4-(dimethylamino)styryl)quinolinium iodide (D36) and (E)-1-butyl-4-(4-hydroxystyryl)quinolinium iodide (D34), were compared in terms of their properties by single-crystal X-ray diffraction (XRD), Hirshfeld surface analysis, Fourier transform Raman (FT-Raman), Fourier transform infrared (FT-IR), fluorescence, and ultraviolet–visible (UV–Vis) spectroscopy, and 1H- and 13C-NMR methods. Both dyes D36 and D34 crystallized in the triclinic and monoclinic systems in the centrosymmetric space groups P-1 and P21/n, respectively. The unit cell of D36 contains two molecules of the dye, participating in weak intermolecular interactions, whereas that of D34 contains four formula units. The phenolic hydroxy group of D34 participates in the formation of a hydrogen bond with the iodide anion. The 4-styrylquinolinium moieties of the cationic dye molecules are nearly planar. The dihedral angle between the mean planes through the ten-membered quinolinium system and the benzene ring is 7.5° in D36 and 5.9(1)° in D34. The structural parameters planarity and bond length alternation (BLA) are discussed, which are important for the evaluation of the first hyperpolarizability β at the molecular level, even in a centrosymmetric crystal. The UV–visible spectra of the dyes in 14 solvents of different polarities were investigated. The reversible solvatochromic behavior of the dyes is demonstrated experimentally and compared with known “binuclear dyes” by evaluating the Rezende model. Dye D36 does not fluoresce, and D34 has a very low emission in the solvents tested. |
| first_indexed | 2024-04-24T07:22:23Z |
| format | Article |
| id | doaj.art-bd9a3f065b944fe0804c42cc3c0fe26e |
| institution | Directory Open Access Journal |
| issn | 2405-8440 |
| language | English |
| last_indexed | 2024-04-24T07:22:23Z |
| publishDate | 2024-04-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Heliyon |
| spelling | doaj.art-bd9a3f065b944fe0804c42cc3c0fe26e2024-04-21T04:14:27ZengElsevierHeliyon2405-84402024-04-01108e29315Comparing the crystal structures and spectroscopic properties of a p-hydroxy styrylquinolinium dye with those of its p-dimethylamino analogueMina Todorova0Rüdiger W. Seidel1Mihaela Stoyanova2Tsonko M. Kolev3Rumyana Bakalska4Plovdiv University, Faculty of Chemistry, 24 Tzar Assen Str., 4000, Plovdiv, BulgariaRuhr-Universität Bochum, Lehrstuhl für Analytische Chemie, Universitätsstraße 150, 44801, Bochum, GermanyPlovdiv University, Faculty of Chemistry, 24 Tzar Assen Str., 4000, Plovdiv, BulgariaInstitute of Molecular Biology “R. Tsanev”, Acad. G. Bonchev Str, bl. 21, 1113, Sofia, BulgariaPlovdiv University, Faculty of Chemistry, 24 Tzar Assen Str., 4000, Plovdiv, Bulgaria; Corresponding author.Two previously synthesized styrylquinolinium dyes, namely (E)-1-butyl-4-(4-(dimethylamino)styryl)quinolinium iodide (D36) and (E)-1-butyl-4-(4-hydroxystyryl)quinolinium iodide (D34), were compared in terms of their properties by single-crystal X-ray diffraction (XRD), Hirshfeld surface analysis, Fourier transform Raman (FT-Raman), Fourier transform infrared (FT-IR), fluorescence, and ultraviolet–visible (UV–Vis) spectroscopy, and 1H- and 13C-NMR methods. Both dyes D36 and D34 crystallized in the triclinic and monoclinic systems in the centrosymmetric space groups P-1 and P21/n, respectively. The unit cell of D36 contains two molecules of the dye, participating in weak intermolecular interactions, whereas that of D34 contains four formula units. The phenolic hydroxy group of D34 participates in the formation of a hydrogen bond with the iodide anion. The 4-styrylquinolinium moieties of the cationic dye molecules are nearly planar. The dihedral angle between the mean planes through the ten-membered quinolinium system and the benzene ring is 7.5° in D36 and 5.9(1)° in D34. The structural parameters planarity and bond length alternation (BLA) are discussed, which are important for the evaluation of the first hyperpolarizability β at the molecular level, even in a centrosymmetric crystal. The UV–visible spectra of the dyes in 14 solvents of different polarities were investigated. The reversible solvatochromic behavior of the dyes is demonstrated experimentally and compared with known “binuclear dyes” by evaluating the Rezende model. Dye D36 does not fluoresce, and D34 has a very low emission in the solvents tested.http://www.sciencedirect.com/science/article/pii/S2405844024053465Stilbazolium dyeHirshfeld surface analysisX-ray crystallographyCrystal structureReversal solvatochromismBLA |
| spellingShingle | Mina Todorova Rüdiger W. Seidel Mihaela Stoyanova Tsonko M. Kolev Rumyana Bakalska Comparing the crystal structures and spectroscopic properties of a p-hydroxy styrylquinolinium dye with those of its p-dimethylamino analogue Heliyon Stilbazolium dye Hirshfeld surface analysis X-ray crystallography Crystal structure Reversal solvatochromism BLA |
| title | Comparing the crystal structures and spectroscopic properties of a p-hydroxy styrylquinolinium dye with those of its p-dimethylamino analogue |
| title_full | Comparing the crystal structures and spectroscopic properties of a p-hydroxy styrylquinolinium dye with those of its p-dimethylamino analogue |
| title_fullStr | Comparing the crystal structures and spectroscopic properties of a p-hydroxy styrylquinolinium dye with those of its p-dimethylamino analogue |
| title_full_unstemmed | Comparing the crystal structures and spectroscopic properties of a p-hydroxy styrylquinolinium dye with those of its p-dimethylamino analogue |
| title_short | Comparing the crystal structures and spectroscopic properties of a p-hydroxy styrylquinolinium dye with those of its p-dimethylamino analogue |
| title_sort | comparing the crystal structures and spectroscopic properties of a p hydroxy styrylquinolinium dye with those of its p dimethylamino analogue |
| topic | Stilbazolium dye Hirshfeld surface analysis X-ray crystallography Crystal structure Reversal solvatochromism BLA |
| url | http://www.sciencedirect.com/science/article/pii/S2405844024053465 |
| work_keys_str_mv | AT minatodorova comparingthecrystalstructuresandspectroscopicpropertiesofaphydroxystyrylquinoliniumdyewiththoseofitspdimethylaminoanalogue AT rudigerwseidel comparingthecrystalstructuresandspectroscopicpropertiesofaphydroxystyrylquinoliniumdyewiththoseofitspdimethylaminoanalogue AT mihaelastoyanova comparingthecrystalstructuresandspectroscopicpropertiesofaphydroxystyrylquinoliniumdyewiththoseofitspdimethylaminoanalogue AT tsonkomkolev comparingthecrystalstructuresandspectroscopicpropertiesofaphydroxystyrylquinoliniumdyewiththoseofitspdimethylaminoanalogue AT rumyanabakalska comparingthecrystalstructuresandspectroscopicpropertiesofaphydroxystyrylquinoliniumdyewiththoseofitspdimethylaminoanalogue |