C3-symmetric triarylboron building blocks: Synthesis, structures, and photophysical properties

IF 2.1 3区 化学 Q3 CHEMISTRY, INORGANIC & NUCLEAR Journal of Organometallic Chemistry Pub Date : 2024-10-24 DOI:10.1016/j.jorganchem.2024.123412
Vishal Singh, Ramaswamy Murugavel
{"title":"C3-symmetric triarylboron building blocks: Synthesis, structures, and photophysical properties","authors":"Vishal Singh,&nbsp;Ramaswamy Murugavel","doi":"10.1016/j.jorganchem.2024.123412","DOIUrl":null,"url":null,"abstract":"<div><div>Synthesis of C<sub>3</sub>-symmetric triarylboranes, tris(4-bromo-2,6-dimethylphenyl)-borane <strong>(1)</strong>, N,N',N''-(boranetriyltris(3,5-diisopropyl-3′,5′-dimethyl-[1,1′-biphenyl]-4′,4-diyl))tris(1,1-diphenylmethanimine) (<strong>2</strong>), N,N',N''-(boranetriyltris(3′,5′-dimethyl-[1,1′-biphenyl]-4′,4-diyl))tris-(1,1-diphenylmethanimine) (<strong>3</strong>), 4′,4′'',4′''''-boranetriyltris(3′,5′-dimethyl-[1,1′-biphenyl]-4-carbaldehyde) (<strong>4),</strong> 4,4′,4′'-boranetriyltris(3,5-dimethylaniline) (<strong>5</strong>), 4′,4′'',4′''''-borane-triyltris(3′,5′-dimethyl-[1,1′-biphenyl]-4-carbonitrile) (<strong>6</strong>), 4′,4′'',4′''''-boranetriyltris(3′,5′-dimethyl-[1,1′-biphenyl]-4-amine) (<strong>7</strong>), and 4,4′,4′'-boranetriyltris(3,5-dimethylbenzaldehyde) (<strong>8</strong>) has been accomplished using well-known synthetic methodologies. These new potential building blocks have been characterized by various spectroscopic and analytical techniques and their photophysical properties have been examined. It is observed that photophysical properties of these compounds are enhanced with π conjugation expansions along the branches when donor moieties such as -NH<sub>2</sub> groups are present at the para-position of the aryl rings. The highest quantum yield of 0.293 is observed for 4′,4′'',4′''''-boranetriyltris(3′,5′-dimethyl-[1,1′-biphenyl]-4-amine) (<strong>7</strong>). Interestingly, red-shifted fluorescence spectra follow the same trend as absorption spectra. The fluorescence lifetime increases with the number of donor moieties. The present findings demonstrate the possible use of these C<sub>3</sub>-symmetric boron-containing building blocks in developing new polymeric materials with improved photophysical properties for various applications.</div></div>","PeriodicalId":374,"journal":{"name":"Journal of Organometallic Chemistry","volume":"1022 ","pages":"Article 123412"},"PeriodicalIF":2.1000,"publicationDate":"2024-10-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Organometallic Chemistry","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0022328X24004078","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, INORGANIC & NUCLEAR","Score":null,"Total":0}
引用次数: 0

Abstract

Synthesis of C3-symmetric triarylboranes, tris(4-bromo-2,6-dimethylphenyl)-borane (1), N,N',N''-(boranetriyltris(3,5-diisopropyl-3′,5′-dimethyl-[1,1′-biphenyl]-4′,4-diyl))tris(1,1-diphenylmethanimine) (2), N,N',N''-(boranetriyltris(3′,5′-dimethyl-[1,1′-biphenyl]-4′,4-diyl))tris-(1,1-diphenylmethanimine) (3), 4′,4′'',4′''''-boranetriyltris(3′,5′-dimethyl-[1,1′-biphenyl]-4-carbaldehyde) (4), 4,4′,4′'-boranetriyltris(3,5-dimethylaniline) (5), 4′,4′'',4′''''-borane-triyltris(3′,5′-dimethyl-[1,1′-biphenyl]-4-carbonitrile) (6), 4′,4′'',4′''''-boranetriyltris(3′,5′-dimethyl-[1,1′-biphenyl]-4-amine) (7), and 4,4′,4′'-boranetriyltris(3,5-dimethylbenzaldehyde) (8) has been accomplished using well-known synthetic methodologies. These new potential building blocks have been characterized by various spectroscopic and analytical techniques and their photophysical properties have been examined. It is observed that photophysical properties of these compounds are enhanced with π conjugation expansions along the branches when donor moieties such as -NH2 groups are present at the para-position of the aryl rings. The highest quantum yield of 0.293 is observed for 4′,4′'',4′''''-boranetriyltris(3′,5′-dimethyl-[1,1′-biphenyl]-4-amine) (7). Interestingly, red-shifted fluorescence spectra follow the same trend as absorption spectra. The fluorescence lifetime increases with the number of donor moieties. The present findings demonstrate the possible use of these C3-symmetric boron-containing building blocks in developing new polymeric materials with improved photophysical properties for various applications.

Abstract Image

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
C3 对称三芳基硼构件:合成、结构和光物理性质
合成 C3 对称三芳基硼烷、三(4-溴-2,6-二甲基苯基)-硼烷 (1)、N,N',N''-(硼烷三(3,5-二异丙基-3′,5′-二甲基-[1,1′-联苯]-4′,4-二基))三(1、(2)、N,N',N''-(硼烷三乙基三(3′,5′-二甲基-[1,1′-联苯]-4′,4-二基))三(1,1-二苯基甲亚胺)(3)、4′,4′'',4′''''-硼烷三乙基三(3′,5′-二甲基-[1、1′-联苯]-4-甲醛)(4), 4,4′,4′'-硼烷三乙烷(3,5-二甲基苯胺)(5), 4′,4′'',4′''''-硼烷三乙烷(3′,5′-二甲基-[1,1′-联苯]-4-甲腈)(6), 4′,4′''、4′''''-硼烷三乙基三(3′,5′-二甲基-[1,1′-联苯]-4-胺)(7)和 4,4′,4′'-硼烷三乙基三(3,5-二甲基苯甲醛)(8)已采用著名的合成方法完成。通过各种光谱和分析技术对这些新的潜在构筑模块进行了表征,并研究了它们的光物理性质。结果表明,当芳基环的对位存在供体分子(如 -NH2 基团)时,这些化合物的光物理特性会随着π共轭沿分支的扩展而增强。4′,4′'',4′''''-硼烷三乙基三(3′,5′-二甲基-[1,1′-联苯]-4-胺)的量子产率最高,达到 0.293 (7)。有趣的是,红移荧光光谱与吸收光谱的趋势相同。荧光寿命随着供体分子数量的增加而增加。本研究结果表明,这些 C3 对称含硼构筑模块可用于开发具有更好光物理性质的新型聚合物材料,并可应用于各种领域。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
求助全文
约1分钟内获得全文 去求助
来源期刊
Journal of Organometallic Chemistry
Journal of Organometallic Chemistry 化学-无机化学与核化学
CiteScore
4.40
自引率
8.70%
发文量
221
审稿时长
36 days
期刊介绍: The Journal of Organometallic Chemistry targets original papers dealing with theoretical aspects, structural chemistry, synthesis, physical and chemical properties (including reaction mechanisms), and practical applications of organometallic compounds. Organometallic compounds are defined as compounds that contain metal - carbon bonds. The term metal includes all alkali and alkaline earth metals, all transition metals and the lanthanides and actinides in the Periodic Table. Metalloids including the elements in Group 13 and the heavier members of the Groups 14 - 16 are also included. The term chemistry includes syntheses, characterizations and reaction chemistry of all such compounds. Research reports based on use of organometallic complexes in bioorganometallic chemistry, medicine, material sciences, homogeneous catalysis and energy conversion are also welcome. The scope of the journal has been enlarged to encompass important research on organometallic complexes in bioorganometallic chemistry and material sciences, and of heavier main group elements in organometallic chemistry. The journal also publishes review articles, short communications and notes.
期刊最新文献
Direct CO2 hydrogenation over Na and CeO2-promoted Iron and Cobalt-based Catalysts Supported on MCM-41 Second sphere control of CO2 reduction selectivity by iron porphyrins: The role of spin state Low-intensity-visible-light-driven photocatalytic CO2 reduction by rhenium tricarbonyl complexes based on pyridyl-triazole ligands Sidearm modified phosphine ligands for Rh complex-catalyzed hydroformylation: Mechanistic pathway and structure-activity relationship Editorial Board
×
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