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
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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.

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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。
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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.
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Editorial Board Contents continued Graphical abstract TOC Graphical abstract TOC Synthesis and catalytic application to form cyclic carbonates of novel Pd(II) Cu(II), and Fe(II) benzoate-based Schiff base metal complexes
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