3H-Pyrrolo-（1,2-a）吲哚基荧光团大环的合成及其稳定的阳离子自由基,Asian Journal of Organic Chemistry

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3H-Pyrrolo-（1,2-a）吲哚基荧光团大环的合成及其稳定的阳离子自由基
Asian Journal of Organic Chemistry ( IF 2.8 ) Pub Date : 2021-02-18 , DOI: 10.1002/ajoc.202100068
Belarani Ojha ₁ , Kandala Laxman ₁ , Mangalampalli Ravikanth ₂

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具有高量子产率的小分子荧光团特别受关注，因为它们在从离子传感到生物成像的多种应用中都发挥着作用。基于吲哚的生物分子因其荧光特性而众所周知。吡咯并[1,2- a ]吲哚由于其在生物医学和染料敏化太阳能电池（DSSC）等各个领域的应用而引起了人们的极大兴趣。在本文中，我们报道了新类型的合成冠3 ħ吡咯并[1,2-一个]吲哚荧光团的大环1 - 3，其使用简单的反应条件下可商购的化合物在30-35％的产率制备。这些荧光团大环1 –通过HR-MS，1D和2D NMR，X射线晶体学，吸收，荧光，电化学和DFT / TD-DFT研究对3个样品进行了表征。荧光团1 - 3中的465-480纳米，发射区域吸收具有大的斯托克斯位移（〜150纳米），10-20％的量子产率，和1.70-2.50纳秒单重态寿命615-645纳米的区域。电化学研究表明，大环1 - 3是富电子和经历更容易氧化。大环1 - 3个通过化学和电化学氧化容易形成阳离子基团，其在低温下以及在室温下是高度稳定的。

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Synthesis of 3H‐Pyrrolo‐(1,2‐a) Indole‐based Fluorophore Macrocycles and their Stable Cation Radicals

Small molecular fluorophores with high quantum yields are of particular interest because of their role in several applications that range from ion sensing to bioimaging. Indole based biomolecules are well known for their fluorescence properties. Pyrrolo[1,2‐a]indoles have gained tremendous interest in recent times due to their applicability in various fields such as biomedicine and dye‐sensitized solar cells (DSSC). In this article, we report the synthesis of new types of crowned 3H‐pyrrolo[1,2‐a]indole fluorophore macrocycles 1–3 which were prepared in 30–35% yields using commercially available compounds under simple reaction conditions. These fluorophore macrocycles 1–3 were characterized by HR‐MS, 1D & 2D NMR, X‐ray crystallography, absorption, fluorescence, electrochemical, and DFT/TD‐DFT studies. The fluorophores 1–3 absorb in the region of 465–480 nm and emit in the region of 615–645 nm with large Stokes shift (∼150 nm), 10–20% quantum yields, and singlet state lifetimes of 1.70–2.50 ns. The electrochemical studies revealed that macrocycles 1–3 are electron‐rich and undergo easier oxidations. The macrocycles 1–3 readily form cation radicals by chemical and electrochemical oxidation which are highly stable at low temperatures as well as at room temperature.

更新日期：2021-04-19

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