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Investigating the change in the photophysical properties of a trio of tetraphenylcyclopentadienone derivatives with varied groups on the aromatic rings in the 3‐ and 4‐positions
Luminescence ( IF 3.2 ) Pub Date : 2020-08-29 , DOI: 10.1002/bio.3944 Arnoldo J Orozco 1 , Kole Joachim 1 , Henry D Ruiz 1 , Frank R Fronczek 2 , Ralph Isovitsch 1
Luminescence ( IF 3.2 ) Pub Date : 2020-08-29 , DOI: 10.1002/bio.3944 Arnoldo J Orozco 1 , Kole Joachim 1 , Henry D Ruiz 1 , Frank R Fronczek 2 , Ralph Isovitsch 1
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Organic compounds with electronic properties, such as a small band gap, are useful in areas ranging from organic field effect transistors to solar cells. Such organic compounds can possess conjugation and/or aromatic systems, with one example being tetraphenylcyclopentadienone and its derivatives. A trio of dramatically coloured tetraphenylcyclopentadienone derivatives with varied substituents on the aromatic rings in the 3‐ and 4‐positions were prepared. Their identities were confirmed using the usual methods, for example 1H nuclear magnetic resonance (NMR) spectroscopy, and their purity quantified using elemental analysis. The X‐ray crystal structure of compound 2 was determined. Its notable structural features involved the cyclopentadienone core with its distinct C−C and C=C bond lengths and its overall nonplanarity, both of which served to mitigate its antiaromatic nature. Chloroform solutions of compounds 2–4 exhibited absorption spectra with three absorption bands at approximately 250, 350, and 500 nm that were assigned to (π)→(π*) transitions. Computational chemistry methods assisted in assigning the observed transitions to a specific molecular orbital combination in the structures of 2–4. Emission in the red end of the visible spectrum (550–625 nm) was observed from chloroform solutions of all three of the prepared compounds.
中文翻译：
研究三和四位芳香环上具有不同基团的三苯基环戊二烯酮衍生物的光物理性质的变化
具有电子特性（例如小带隙）的有机化合物可用于有机场效应晶体管到太阳能电池等领域。这样的有机化合物可以具有共轭和/或芳族体系，一个例子是四苯基环戊二烯酮及其衍生物。制备了三色的显色四苯基环戊二烯酮衍生物，这些衍生物在3位和4位芳香环上具有不同的取代基。使用常规方法（例如1 H核磁共振（NMR）光谱）确认其身份，并使用元素分析对其纯度进行定量。化合物2的X射线晶体结构被确定。它的显着结构特征涉及具有独特的C-C和C = C键长以及整体非平面性的环戊二烯酮核心，两者均有助于减轻其抗芳香性。化合物的氯仿溶液2 - 4展出吸收光谱具有三个吸收带在约250，350，和500nm已分配给（π）→（π*）的转换。计算化学方法有助于将观察到的跃迁分配给2 – 4结构中的特定分子轨道组合。从所有三种制备的化合物的氯仿溶液中观察到可见光谱的红色端（550-625 nm）的发射。
更新日期：2020-08-29
中文翻译：
研究三和四位芳香环上具有不同基团的三苯基环戊二烯酮衍生物的光物理性质的变化
具有电子特性（例如小带隙）的有机化合物可用于有机场效应晶体管到太阳能电池等领域。这样的有机化合物可以具有共轭和/或芳族体系，一个例子是四苯基环戊二烯酮及其衍生物。制备了三色的显色四苯基环戊二烯酮衍生物，这些衍生物在3位和4位芳香环上具有不同的取代基。使用常规方法（例如1 H核磁共振（NMR）光谱）确认其身份，并使用元素分析对其纯度进行定量。化合物2的X射线晶体结构被确定。它的显着结构特征涉及具有独特的C-C和C = C键长以及整体非平面性的环戊二烯酮核心，两者均有助于减轻其抗芳香性。化合物的氯仿溶液2 - 4展出吸收光谱具有三个吸收带在约250，350，和500nm已分配给（π）→（π*）的转换。计算化学方法有助于将观察到的跃迁分配给2 – 4结构中的特定分子轨道组合。从所有三种制备的化合物的氯仿溶液中观察到可见光谱的红色端（550-625 nm）的发射。
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