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Synthesis, photophysical evaluation, and computational study of 2-methoxy- and 2-morpholino pyridine compounds as highly emissive fluorophores in solution and the solid state
http://hdl.handle.net/10069/39381
http://hdl.handle.net/10069/393818b326a62-bced-432c-ad6c-42013c710225
名前 / ファイル | ライセンス | アクション |
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DyePig171_107705.pdf (2.5 MB)
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Item type | 学術雑誌論文 / Journal Article(1) | |||||
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公開日 | 2020-12-18 | |||||
タイトル | ||||||
タイトル | Synthesis, photophysical evaluation, and computational study of 2-methoxy- and 2-morpholino pyridine compounds as highly emissive fluorophores in solution and the solid state | |||||
言語 | ||||||
言語 | eng | |||||
キーワード | ||||||
主題Scheme | Other | |||||
主題 | Keto-enol tautomerism of 2-pyridone | |||||
キーワード | ||||||
主題Scheme | Other | |||||
主題 | Pyridine | |||||
キーワード | ||||||
主題Scheme | Other | |||||
主題 | Fluorescence | |||||
キーワード | ||||||
主題Scheme | Other | |||||
主題 | TDDFT | |||||
キーワード | ||||||
主題Scheme | Other | |||||
主題 | CASSCF | |||||
キーワード | ||||||
主題Scheme | Other | |||||
主題 | Conical intersection | |||||
資源タイプ | ||||||
資源タイプ識別子 | http://purl.org/coar/resource_type/c_6501 | |||||
資源タイプ | journal article | |||||
著者 |
Hagimori, Masayori
× Hagimori, Masayori× Nishimura, Yasuhisa× Mizuyama, Naoko× Shigemitsu, Yasuhiro |
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抄録 | ||||||
内容記述タイプ | Abstract | |||||
内容記述 | Two 2-pyridone tautomeric analogs, methoxypyridine 4 and N-methylpyridone 5, were synthesized, and their spectroscopic properties were investigated both experimentally and computationally. A detailed photophysical study reveals that 4 shows high fluorescence quantum yields not only in chloroform but also in ethanol, and the strong fluorescence in solution might be attributed to the enol form (pyridine) of the 2-pyridone. Furthermore, we designed and synthesized novel 2-substitued pyridines to achieve more intense emissions in both solution and the solid state. Substituent modification with phenylsulfonyl,morpholino, and 4-diethylamino groups greatly affected the fluorescence properties, and methoxypyridine 7 and morpholinopyridine compound 8 showed fluorescence in various solvents (Ф = 0.59-0.95) and the solid state (Ф = 0.12-0.15). A hypsochromic shift in the emission maximum wavelength and strong fluorescence in the solid state (Ф = 0.39) were observed for dimorpholinopyridine 9. Morpholinopyridine 11 showed intense fluorescence in all nonpolar and polar solvents. Systematic time-dependent density functional theory calculations were performed for the compounds whose electronic and fluorescent maxima were computationally reproduced with good agreement to those from experiment. In detail, the drastic difference in the emission intensity between 4 and 5 in solution was successfully explained using CASSCF calculations, which revealed the presence of conical intersections between the ground and the excited states. | |||||
書誌情報 |
Dyes and Pigments 巻 171, p. 107705, 発行日 2019-07-10 |
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出版者 | ||||||
出版者 | Elsevier Ltd | |||||
ISSN | ||||||
収録物識別子タイプ | ISSN | |||||
収録物識別子 | 01437208 | |||||
DOI | ||||||
関連タイプ | isVersionOf | |||||
識別子タイプ | DOI | |||||
関連識別子 | 10.1016/j.dyepig.2019.107705 | |||||
権利 | ||||||
権利情報 | c 2019 Elsevier Ltd. This manuscript version is made available under the CC-BY-NC-ND 4.0 license http://creativecommons.org/licenses/by-nc-nd/4.0/ | |||||
著者版フラグ | ||||||
出版タイプ | AM | |||||
出版タイプResource | http://purl.org/coar/version/c_ab4af688f83e57aa | |||||
引用 | ||||||
内容記述タイプ | Other | |||||
内容記述 | Dyes and Pigments, 171, art.no.107705; 2019 |