Synthesis and photochromic properties of 4,5-bisaryl-3(2H)-pyridazinones
Six novel photochromic bisarylpyridazinones containing 2,5-dimethylthiophene or 5-methyl-2-phenylthiazole unit were synthesized, and their photochromic and fluorescence properties were investigated. The bisarylpyridazinones underwent reversible color change upon irradiation with UV or visible light. The effect of solvents on the absorption spectra of the bisarylpyridazinones was investigated. The closed-ring forms of bisarylpyridazinones displayed negative solvatochromism which was attributed to the high dipolar characters of the molecule. The open-ring forms of bisarylpyridazinones showed fluorescence at 400-480 nm upon excitation at 302 nm, and the intensities of emission bands gradually decreased during the ring-closing photoreactions. Among the synthesized bisarylpyridazinones, 4,5-bis(5-methyl-2-phenylthiazol-4-yl)-2-methyl(or 2-phenyl) pyridazin-3(2H)-ones (5O and 6O) displayed rather large absorption and emission spectral change, higher quantum efficiency during the photoreaction compared to others. A high conversion ratio (94%) to the closed form was observed for 5O. © 2015 Elsevier B.V. All rights reserved.
| Yazar |
Orhan E. Gundogdu L. Kose M. Yokoyama Y. |
| Yayın Türü | Article |
| Tek Biçim Adres | https://hdl.handle.net/20.500.12628/7754 |
| Tek Biçim Adres | 10.1016/j.jphotochem.2015.08.025 |
| Konu Başlıkları |
Bisarylpyridazinone
Diarylethene Fluorescence switch Photochromism Pyridazinone Solvent effect |
| Koleksiyonlar |
Araştırma Çıktıları | WoS | Scopus | TR-Dizin | PubMed | SOBİAD Scopus İndeksli Yayınlar Koleksiyonu WoS İndeksli Yayınlar Koleksiyonu |
| Dergi Adı | Journal of Photochemistry and Photobiology A: Chemistry |
| Dergi Cilt Bilgisi | 314 |
| Sayfalar | 164 - 170 |
| Yayın Yılı | 2016 |
| Eser Adı [dc.title] | Synthesis and photochromic properties of 4,5-bisaryl-3(2H)-pyridazinones |
| Yazar [dc.contributor.author] | Orhan E. |
| Yazar [dc.contributor.author] | Gundogdu L. |
| Yazar [dc.contributor.author] | Kose M. |
| Yazar [dc.contributor.author] | Yokoyama Y. |
| Yayın Yılı [dc.date.issued] | 2016 |
| Yayıncı [dc.publisher] | Elsevier |
| Yayın Türü [dc.type] | article |
| Özet [dc.description.abstract] | Six novel photochromic bisarylpyridazinones containing 2,5-dimethylthiophene or 5-methyl-2-phenylthiazole unit were synthesized, and their photochromic and fluorescence properties were investigated. The bisarylpyridazinones underwent reversible color change upon irradiation with UV or visible light. The effect of solvents on the absorption spectra of the bisarylpyridazinones was investigated. The closed-ring forms of bisarylpyridazinones displayed negative solvatochromism which was attributed to the high dipolar characters of the molecule. The open-ring forms of bisarylpyridazinones showed fluorescence at 400-480 nm upon excitation at 302 nm, and the intensities of emission bands gradually decreased during the ring-closing photoreactions. Among the synthesized bisarylpyridazinones, 4,5-bis(5-methyl-2-phenylthiazol-4-yl)-2-methyl(or 2-phenyl) pyridazin-3(2H)-ones (5O and 6O) displayed rather large absorption and emission spectral change, higher quantum efficiency during the photoreaction compared to others. A high conversion ratio (94%) to the closed form was observed for 5O. © 2015 Elsevier B.V. All rights reserved. |
| Kayıt Giriş Tarihi [dc.date.accessioned] | 2019-12-23 |
| Açık Erişim Tarihi [dc.date.available] | 2019-12-23 |
| Yayın Dili [dc.language.iso] | eng |
| Konu Başlıkları [dc.subject] | Bisarylpyridazinone |
| Konu Başlıkları [dc.subject] | Diarylethene |
| Konu Başlıkları [dc.subject] | Fluorescence switch |
| Konu Başlıkları [dc.subject] | Photochromism |
| Konu Başlıkları [dc.subject] | Pyridazinone |
| Konu Başlıkları [dc.subject] | Solvent effect |
| Haklar [dc.rights] | info:eu-repo/semantics/closedAccess |
| ISSN [dc.identifier.issn] | 1010-6030 |
| Sponsor YAYINCI [dc.description.sponsorship] | 113Z547 |
| Sponsor YAYINCI [dc.description.sponsorship] | The authors are grateful to TUBITAK (Scientific and Technical Research Council of Turkey) for the financial support of this work (Grant No: 113Z547). The authors are grateful to the Bülent Ecevit University Editing Office for editing our article. |
| İlk Sayfa Sayısı [dc.identifier.startpage] | 164 |
| Son Sayfa Sayısı [dc.identifier.endpage] | 170 |
| Dergi Adı [dc.relation.journal] | Journal of Photochemistry and Photobiology A: Chemistry |
| Dergi Cilt Bilgisi [dc.identifier.volume] | 314 |
| Tek Biçim Adres [dc.identifier.uri] | https://dx.doi.org/10.1016/j.jphotochem.2015.08.025 |
| Tek Biçim Adres [dc.identifier.uri] | https://hdl.handle.net/20.500.12628/7754 |
