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首页> 外文期刊>RSC Advances >meso-Aryl substituted free-base tripyrrins: preparation and electrochemically induced protonation/deprotonation reactions. Single crystal X-ray analysis of (2,6-diFPh)(2)TriPyH
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meso-Aryl substituted free-base tripyrrins: preparation and electrochemically induced protonation/deprotonation reactions. Single crystal X-ray analysis of (2,6-diFPh)(2)TriPyH

机译：内消旋芳基取代的游离基三联吡啶：制备和电化学诱导的质子化/去质子化反应。 （2,6-diFPh）（2）TriPyH的单晶X射线分析

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摘要

Three meso-substituted pyrrole-terminated tripyrrins were isolated for the first time as side products in the synthesis of triarylcorroles and characterized by spectroscopic and electrochemical techniques. The examined compounds are represented as (Ar)(2)TriPyH, where the TriPy is the conjugated tripyrrin monoanion and Ar a 2,6-diFPh, 2,6-diClPh or 2,4-diClPh substituent. A single crystal X-ray structure of (2,6-diFPh)(2)TriPyH is also presented. This is the first X-ray structure of a meso-aryl substituted tripyrrin. Each tripyrrin undergoes two reductions and three oxidations in CH2Cl2. The first one-electron addition and first one-electron abstraction lead to formation of pi-anion and pi-cation radicals with a potential separation between the two processes of 1.71 to 1.76 V. However, both electrogenerated products are unstable and undergo a rapid chemical reaction to give new electroactive species which are identified as the deprotonated and protonated compounds, respectively. The reaction products were characterized by spectroelectrochemistry and comparisons are made with spectroscopic data obtained during base and acid titrations in CH2Cl2.
机译：首次分离了三种内消旋取代的吡咯封端的三联吡啶作为副产物，合成了三芳基苯酚，并通过光谱和电化学技术对其进行了表征。所检查的化合物表示为（Ar）（2）TriPyH，其中TriPy是共轭的三联吡啶单阴离子，Ar是2,6-diFPh，2,6-diClPh或2,4-diClPh取代基。还提出了（2,6-diFPh）（2）TriPyH的单晶X射线结构。这是中芳基取代的三磷酸酪氨酸的第一个X射线结构。每个三联吡啶在CH2Cl2中经历两次还原和三次氧化。第一次单电子加成和第一次单电子提取导致形成pi-阴离子和pi-阳离子自由基，两个过程之间的电位差为1.71至1.76V。但是，这两种电生成的产物都很不稳定，并且会经历快速化学反应。反应得到新的电活性物质，分别被鉴定为去质子化和质子化的化合物。通过光谱电化学表征反应产物，并与在CH 2 Cl 2中的碱和酸滴定过程中获得的光谱数据进行比较。

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