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Synthesis and photophysical properties of fluorescent dyes based on triphenylamine, diphenylamine, diphenyl sulfone or triphenyltriazine derivatives containing an acetylene linkage group
Dyes and Pigments ( IF 4.1 ) Pub Date : 2020-06-06 , DOI: 10.1016/j.dyepig.2020.108617
Kyung-Won Kim , Su-Hyeon Kwon , Byung-Jun Lee , Sung-Ok Ahn , Ju-Hong Lee , Jae-Hong Choi

In this study, ten fluorescent dyes were prepared based on three different kinds of central moiety, such as triphenylamine, diphenylsulfone or triphenyltriazine, which was coupled to either carbazole or naphthalimidinyl group via an acetylene linkage group. N-n-Butyl-carbazole, N-phenyl-carbazole or N-n-butyl-naphthalimide was coupled to the individual central moiety of triphenylamine, diphenyl sulfone, 2,4,6-triphenyl-1,3,5-trazine or diphenylamine using a Sonogashira coupling reaction in the final step. All dyes were confirmed their chemical structure by 1H NMR, GC-Mass and elemental analyses. The absorption properties and thermal stabilities of the fluorescent dyes were examined. Density Functional Theory (DFT) and Time-Dependent DFT calculations were carried out, in addition to geometry simulation, by using the Gaussian 09 program. In terms of fluorescence properties in this series, two dyes based on diphenyl sulfonyl and three dyes based on triphenylamine substituted by 1–3 of N-n-butyl-carbazole exhibited a blue emission, whereas three dyes based on triphenylamine substituted by 1–3 of N-n-butyl-naphthalimide were observed by a red emitter which can be attributable to both effects the bathochromic shifts in absorption maxima and larger Stokes shifts. In case of corresponding 2,4,6-triphenyl-1,3,5-trazine central moiety coupled to a carbazole ring, a green fluorescence was emitted. Results revealed that the fluorescence of the dyes is affected by the electron-donating strength of the acetylene linkages involved in the π-conjugation systems of the dyes.



中文翻译:

基于含有乙炔键的三苯胺,二苯胺,二苯砜或三苯基三嗪衍生物的荧光染料的合成和光物理性质

在这项研究中,基于三种不同类型的中心部分(例如三苯胺,二苯砜或三苯基三嗪)制备了十种荧光染料,它们通过乙炔键连接到咔唑或萘二甲酰亚胺基上。ñ - Ñ丁基咔唑,ñ -苯基咔唑或ñ - ñ丁基萘二甲酰亚胺偶联到三苯胺的各个中央部分,二苯基砜,2,4,6-三苯基-1,3,5-川芎嗪或在最后一步中使用Sonogashira偶联反应合成二苯胺。通过1确认所有染料的化学结构1 H NMR,GC-质谱和元素分析。检查了荧光染料的吸收特性和热稳定性。除几何模拟外,还使用高斯09程序进行了密度泛函理论(DFT)和时变DFT计算。在本系列荧光特性方面,两种染料基于二苯基磺酰基和基于由三苯胺的1-3个所取代三种染料ñ - ñ丁基咔唑表现出发蓝色荧光,而基于三苯胺三种染料被1-3取代的的N - n通过红色发射体观察到了丁基丁基萘二甲酰亚胺,这既可归因于吸收最大值的红移,也可归因于较大的斯托克斯位移。在相应的2,4,6-三苯基-1,3,5-嗪中央部分与咔唑环偶联的情况下,发出绿色荧光。结果表明,染料的荧光受染料π共轭体系中乙炔键的供电子强度的影响。

更新日期:2020-06-06
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