甲氧基化双(五氟苯基)硼-β-二酮:合成、光学特性和水解稳定性

IF 3 4区 化学 Q3 CHEMISTRY, PHYSICAL ChemPhotoChem Pub Date : 2024-04-23 DOI:10.1002/cptc.202300317
Maxim V. Filippov, Yuriy N. Kononevich, Dmitry S. Ionov, Andrey A. Safonov, Anastasia I. Karnaeva, Viacheslav A. Sazhnikov, Mikhail V. Alfimov, Aziz M. Muzafarov
{"title":"甲氧基化双(五氟苯基)硼-β-二酮:合成、光学特性和水解稳定性","authors":"Maxim V. Filippov,&nbsp;Yuriy N. Kononevich,&nbsp;Dmitry S. Ionov,&nbsp;Andrey A. Safonov,&nbsp;Anastasia I. Karnaeva,&nbsp;Viacheslav A. Sazhnikov,&nbsp;Mikhail V. Alfimov,&nbsp;Aziz M. Muzafarov","doi":"10.1002/cptc.202300317","DOIUrl":null,"url":null,"abstract":"<p>A series of methoxylated bis(pentafluorophenyl)boron-<i>β</i>-diketonates (dkB(C<sub>6</sub>F<sub>5</sub>)<sub>2</sub>) with intense emission has been synthesized and characterized by a variety of physicochemical methods. The photophysical properties of the synthesized compounds were thoroughly investigated by electronic absorption, steady-state, and time-resolved fluorescence spectroscopy in both solution and solid state. The studied compounds exhibit solvatochromic behavior attributed to the intramolecular charge transfer (ICT) nature of the first excited state. The formation of exciplexes between DBMB(C<sub>6</sub>F<sub>5</sub>)<sub>2</sub> and benzene derivatives was also studied. Notably, the studied compounds display a complex luminescence profile in the solid state, featuring fluorescence, delayed fluorescence and phosphorescence emission. Furthermore, the hydrolytical stability of the complexes was assessed, demonstrating excellent resistance to hydrolysis. Estimated rate constants, determined at 60 °C, are significantly lower (90-2000 times) than those observed for the well-studied dibenzoylmethanatoboron difluoride (DBMBF<sub>2</sub>). The incorporation of pentafluorophenyl substituents at the boron atom enables the synthesis of highly fluorescent and hydrolytically stable boron chelate complexes, suitable for sensing and bioimaging applications in water-containing environments.</p>","PeriodicalId":10108,"journal":{"name":"ChemPhotoChem","volume":null,"pages":null},"PeriodicalIF":3.0000,"publicationDate":"2024-04-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Methoxylated bis(pentafluorophenyl)boron-β-diketonates: Synthesis, Optical Properties and Hydrolytic Stability\",\"authors\":\"Maxim V. Filippov,&nbsp;Yuriy N. Kononevich,&nbsp;Dmitry S. Ionov,&nbsp;Andrey A. Safonov,&nbsp;Anastasia I. Karnaeva,&nbsp;Viacheslav A. Sazhnikov,&nbsp;Mikhail V. Alfimov,&nbsp;Aziz M. Muzafarov\",\"doi\":\"10.1002/cptc.202300317\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p>A series of methoxylated bis(pentafluorophenyl)boron-<i>β</i>-diketonates (dkB(C<sub>6</sub>F<sub>5</sub>)<sub>2</sub>) with intense emission has been synthesized and characterized by a variety of physicochemical methods. The photophysical properties of the synthesized compounds were thoroughly investigated by electronic absorption, steady-state, and time-resolved fluorescence spectroscopy in both solution and solid state. The studied compounds exhibit solvatochromic behavior attributed to the intramolecular charge transfer (ICT) nature of the first excited state. The formation of exciplexes between DBMB(C<sub>6</sub>F<sub>5</sub>)<sub>2</sub> and benzene derivatives was also studied. Notably, the studied compounds display a complex luminescence profile in the solid state, featuring fluorescence, delayed fluorescence and phosphorescence emission. Furthermore, the hydrolytical stability of the complexes was assessed, demonstrating excellent resistance to hydrolysis. Estimated rate constants, determined at 60 °C, are significantly lower (90-2000 times) than those observed for the well-studied dibenzoylmethanatoboron difluoride (DBMBF<sub>2</sub>). The incorporation of pentafluorophenyl substituents at the boron atom enables the synthesis of highly fluorescent and hydrolytically stable boron chelate complexes, suitable for sensing and bioimaging applications in water-containing environments.</p>\",\"PeriodicalId\":10108,\"journal\":{\"name\":\"ChemPhotoChem\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":3.0000,\"publicationDate\":\"2024-04-23\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"ChemPhotoChem\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://onlinelibrary.wiley.com/doi/10.1002/cptc.202300317\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q3\",\"JCRName\":\"CHEMISTRY, PHYSICAL\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"ChemPhotoChem","FirstCategoryId":"92","ListUrlMain":"https://onlinelibrary.wiley.com/doi/10.1002/cptc.202300317","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, PHYSICAL","Score":null,"Total":0}
引用次数: 0

摘要

通过多种物理化学方法合成并表征了一系列具有强烈发射的甲氧基化双(五氟苯基)硼-β-二酮酸盐(dkB(C6F5)2)。通过电子吸收、稳态和时间分辨荧光光谱,对合成化合物在溶液和固体状态下的光物理特性进行了深入研究。所研究的化合物表现出溶解变色行为,这归因于第一激发态的分子内电荷转移(ICT)性质。此外,还研究了 DBMB(C6F5)2 与苯衍生物之间形成的共混物。值得注意的是,所研究的化合物在固态下显示出复杂的发光特征,包括荧光、延迟荧光和磷光发射。此外,还对复合物的水解稳定性进行了评估,结果表明其具有出色的抗水解性。在 60 °C 温度下测定的估计速率常数(90-2000 倍)明显低于已被广泛研究的二苯甲酰基甲硼二氟化物(DBMBF2)。在硼原子上加入五氟苯基取代基能够合成高荧光和水解稳定的硼螯合物,适用于含水环境中的传感和生物成像应用。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

摘要图片

查看原文
分享 分享
微信好友 朋友圈 QQ好友 复制链接
本刊更多论文
Methoxylated bis(pentafluorophenyl)boron-β-diketonates: Synthesis, Optical Properties and Hydrolytic Stability

A series of methoxylated bis(pentafluorophenyl)boron-β-diketonates (dkB(C6F5)2) with intense emission has been synthesized and characterized by a variety of physicochemical methods. The photophysical properties of the synthesized compounds were thoroughly investigated by electronic absorption, steady-state, and time-resolved fluorescence spectroscopy in both solution and solid state. The studied compounds exhibit solvatochromic behavior attributed to the intramolecular charge transfer (ICT) nature of the first excited state. The formation of exciplexes between DBMB(C6F5)2 and benzene derivatives was also studied. Notably, the studied compounds display a complex luminescence profile in the solid state, featuring fluorescence, delayed fluorescence and phosphorescence emission. Furthermore, the hydrolytical stability of the complexes was assessed, demonstrating excellent resistance to hydrolysis. Estimated rate constants, determined at 60 °C, are significantly lower (90-2000 times) than those observed for the well-studied dibenzoylmethanatoboron difluoride (DBMBF2). The incorporation of pentafluorophenyl substituents at the boron atom enables the synthesis of highly fluorescent and hydrolytically stable boron chelate complexes, suitable for sensing and bioimaging applications in water-containing environments.

求助全文
通过发布文献求助,成功后即可免费获取论文全文。 去求助
来源期刊
ChemPhotoChem
ChemPhotoChem Chemistry-Physical and Theoretical Chemistry
CiteScore
5.80
自引率
5.40%
发文量
165
期刊最新文献
Front Cover: Diindeno-Fused Corannulene-Extended Tetrathiafulvalenes (ChemPhotoChem 10/2024) Spectroscopic Response of Chiral Proteophenes Binding to Two Chiral Insulin Amyloids Novel Photobase Generators Derived from Proazaphosphatrane–Aryl Borate for High-Pressure Mercury Lamp Lithography Modulating N–H Bond Cleavage in Catalytic Ammonia Oxidation Reaction Design and Synthesis of Aggregation-Caused Quenching Hydroxy-Phenanthroimidazole Derivatives for Probing of Fe3+ ions and as Potential Blue Light Emitters
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
现在去查看 取消
×
提示
确定
0
微信
客服QQ
Book学术公众号 扫码关注我们
反馈
×
意见反馈
请填写您的意见或建议
请填写您的手机或邮箱
已复制链接
已复制链接
快去分享给好友吧!
我知道了
×
扫码分享
扫码分享
Book学术官方微信
Book学术文献互助
Book学术文献互助群
群 号:481959085
Book学术
文献互助 智能选刊 最新文献 互助须知 联系我们:info@booksci.cn
Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。
Copyright © 2023 Book学术 All rights reserved.
ghs 京公网安备 11010802042870号 京ICP备2023020795号-1