1,3-Diylideneisoindolines: Synthesis, Structure, Redox, and Optical Properties,The Journal of Organic Chemistry

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1,3-Diylideneisoindolines: Synthesis, Structure, Redox, and Optical Properties
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2019-04-25 00:00:00 , DOI: 10.1021/acs.joc.9b00468
Yuriy V. Zatsikha ₁ , Briana R. Schrage ₂ , Julia Meyer ₂ , Victor N. Nemykin ₁ , Christopher J. Ziegler ₂

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Diiminoisoindoline (DII) is a crucial reagent for the synthesis of phthalocyanine as well as related macrocycles and chelates such as hemiporphyrazine and bis(iminopyridyl)isoindoline. In this report, we present the synthesis and characterization of four 1,3-diylideneisoindolines prepared via the reaction of several organic CH acids and DII. These orange or red compounds exhibit intense π → π* transitions in the UV–visible region. The redox properties and electronic structures of all new compounds were investigated using cyclic voltammetry and density functional theory (DFT). The observed electrochemistry and UV–visible transitions are in good agreement with the DFT and time-dependent DFT calculations, which indicate that the HOMO is largely centered at the O═C–C–C═O fragments, and the lowest unoccupied molecular orbital is more extended onto the isoindoline unit.

中文翻译：

1,3-二亚甲基二氢吲哚：合成，结构，氧化还原和光学性质

Diiminoisoindoline（DII）是用于合成酞菁以及相关大环化合物和螯合物（例如半卟啉和双（亚氨基吡啶基）异吲哚啉）的重要试剂。在本报告中，我们介绍了通过几种有机CH酸与DII的反应制备的四种1,3-二亚苄基二氢吲哚的合成与表征。这些橙色或红色化合物在紫外可见区域表现出强烈的π→π*跃迁。使用循环伏安法和密度泛函理论（DFT）研究了所有新化合物的氧化还原性质和电子结构。观察到的电化学和紫外可见跃迁与DFT和随时间变化的DFT计算非常吻合，这表明HOMO主要集中在O═C–C–C═O片段上，

更新日期：2019-04-25

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