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Organic superbase-induced chemiluminescent decomposition of a hydroxyaryl-substituted dioxetane: Unique effect of a bifunctional guanidine base on the chemiluminescence profile of a bicyclic dioxetane bearing a 4-(benzoxazol-2-yl)-3,5-dihydroxyphenyl moiety
Tetrahedron Letters ( IF 1.5 ) Pub Date : 2018-01-31 , DOI: 10.1016/j.tetlet.2018.01.045
Nobuko Watanabe , Ayu Wakatsuki , Hisako K. Ijuin , Yoshio Kabe , Masakatsu Matsumoto

Organic superbases represented by TBD (1,5,7-triazabicyclo[4.4.0]dec-5-ene) effectively induced the decomposition of hydroxyaryl-substituted dioxetanes in acetonitrile to give bright light. The color of the chemiluminescence from a dioxetane bearing a 4-(benzoxazol-2-yl)-3,5-dihydroxyphenyl moiety varied depending on the base used. In addition to this change in the color of emission, TBD increased the chemiluminescence efficiency 2- to 5-fold compared to the results with other base systems and accelerated decomposition of the dioxetane. These unique effects of TBD may be due to its “bifunctional” character, which is different from those of other organic superbases. Chemiluminescent decomposition of the dioxetane was effectively induced by superbases even in apolar p-xylene.



中文翻译:

有机超碱诱导的羟芳基取代的二氧杂环丁烷的化学发光分解:双官能胍碱基对带有4-(苯并恶唑-2-基)-3,5-二羟基苯基部分的双环二氧杂环丁烷的化学发光特性的独特影响

以TBD(1,5,7-三氮杂双环[4.4.0] dec-5-ene)为代表的有机超强碱有效地诱导了乙腈中羟芳基取代的二氧杂环丁烷的分解,从而发出明亮的光。来自带有4-(苯并恶唑-2-基)-3,5-二羟基苯基部分的二氧杂环丁烷的化学发光的颜色根据所用的碱而变化。除了发光颜色的这种变化之外,TBD的化学发光效率比其他碱基系统的结果提高了2到5倍,并加速了二氧杂环丁烷的分解。TBD的这些独特作用可能是由于其“双功能”特性,与其他有机超级碱不同。即使在非极性二甲苯中,超碱也有效地诱导了二氧杂环丁烷的化学发光分解。

更新日期:2018-01-31
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