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Synthesis and Photophysical Studies of Novel V‐Shaped 2,3‐Bis{5‐aryl‐2‐thienyl}(dibenzo[f,h])quinoxalines
Asian Journal of Organic Chemistry ( IF 2.7 ) Pub Date : 2020-03-16 , DOI: 10.1002/ajoc.202000038
Tatyana N. Moshkina 1 , Emiliya V. Nosova 1, 2 , Alexandra E. Kopotilova 1 , Galina N. Lipunova 1, 2 , Marina S. Valova 2 , Leila K. Sadieva 1, 2 , Dmitry S. Kopchuk 1, 2 , Pavel A. Slepukhin 1, 2 , Robert Zaleśny 3 , Borys Ośmiałowski 4 , Valery N. Charushin 1, 2
Affiliation  

A series of novel V‐shaped luminophores containing electron‐withdrawing dibenzo[f,h]quinoxaline core and arylthienyl donor fragments at positions 2 and 3 has been synthesized. The absorption spectra (UV/vis) were recorded in several solvents, whereas emission spectra were recorded in solutions and powders. The solvatochromism as well as halochromism of obtained compounds was also explored. Electronic‐structure calculations using quantum‐chemistry methods were performed to further analyse experimental results. All characteristics were compared with that of 2,3‐bis(arylthienyl)quinoxaline counterparts. The halochromic effect studies showed that upon gradual addition of trifluoroacetic acid (TFA) to the toluene solution of diethylaminophenyl‐substituted dibenzo[f,h]quinoxaline chromophore, absorption and emission changed. Observed band shifts were more distinct in the case of mentioned quinoxaline than for other derivatives. All of the (dibenzo[f,h])quinoxaline chromophores exhibited good sensitivity toward nitro‐containing explosives with high Stern‐Volmer constants up to 57800 M−1, these results are remarkable for such heterocyclic systems.

中文翻译:

新型V型2,3-双{5-芳基-2-噻吩基}(二苯并[f,h])喹喔啉的合成与光物理研究

合成了一系列新颖的V形发光体,其在2和3位含有吸电子二苯并[ f,h ]喹喔啉核心和芳基噻吩基供体片段。在几种溶剂中记录了吸收光谱(UV / vis),而在溶液和粉末中记录了发射光谱。还研究了所得化合物的溶剂变色和盐变色。使用量子化学方法进行了电子结构计算,以进一步分析实验结果。将所有特征与2,3-双(芳基噻吩基)喹喔啉对应物进行比较。盐致变色效应研究表明,在将三氟乙酸(TFA)逐渐添加到二乙氨基苯基取代的二苯并[ f,h]的甲苯溶液中喹喔啉生色团,吸收和发射改变。在提到的喹喔啉的情况下,观察到的谱带位移比其他衍生物更明显。所有的(二苯并[ f,h ])喹喔啉生色团都显示出对斯特恩-沃尔默常数高达57800 M -1的含硝基炸药的良好敏感性,这些结果对于此类杂环系统而言是显着的。
更新日期:2020-04-21
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