Facile Synthesis of 9,10,19,20-Tetraarylporphycenes
Facile Synthesis of 9,10,19,20-Tetraarylporphycenes
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DOI：
10.1002/ejoc.201402770
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发表时间：
2014-10-01
影响因子：
2.8
通讯作者：
Ravikanth, Mangalampalli
中科院分区：
文献类型：
--
作者：
Ganapathi, Emandi;Chatterjee, Tamal;Ravikanth, Mangalampalli
通过结合麦克默里（McMurry）反应和氧化合成策略，并使用容易获得的前体，开发了一种合成9,10,19,20 - 四芳基卟吩的简单路线。经过两步制备得到的所需的5,6 - 二芳基二吡咯乙烯（以克为单位大量制备），用于在温和的酸催化条件下制备9,10,19,20 - 四芳基卟吩。由于5,6 - 二芳基二吡咯乙烯前体能够容易地以克为单位大量制备，该方法对于制备含有不同芳基取代基的中位 - 四芳基卟吩是有用的。这些大环化合物的分子结构通过高分辨率质谱（HRMS）分析以及一维和二维核磁共振（NMR）研究确定。四芳基卟吩在约380 nm处显示出强的索雷特（Soret）带，在580 - 655 nm区域有三个Q带。四芳基卟吩具有适度的荧光性，并且在氧化还原条件下稳定。
A simple route was developed for the synthesis of 9,10,19,20-tetraarylporphycenes by combining both McMurry and oxidative synthetic strategies and using readily available precursors. The desired 5,6-diaryldipyrroethenes, which were prepared in multigram quantities over two steps, were used to prepare 9,10,19,20-tetraarylporphycenes under mild acid-catalyzed conditions. As 5,6-diaryldipyrroethene precursors can easily be prepared in multigram quantities, this method is useful for the preparation of meso-tetrarylporphycenes that contain different aryl substituents. The molecular structures of these macrocycles were determined by HRMS analysis as well as 1D and 2D NMR studies. The tetraarylporphycenes exhibited a strong Soret band at approximately 380 nm and three Q bands in the region of 580-655 nm. The tetraarylprophycenes are reasonably fluorescent and stable under redox conditions.