Ngo T H, Labuta J, Lim G N, Webre W A, D'Souza F, Karr P A, Lewis J E M, Hill J P, Ariga K, Goldup S M
International Center for Young Scientists (ICYS) , WPI Center for Materials Nanoarchitectonics (WPI-MANA) , National Institute for Materials Science , Namiki 1-1 , Tsukuba , Ibaraki 305-0044 , Japan . Email:
WPI Center for Materials Nanoarchitectonics , National Institute for Materials Science , Namiki 1-1 , Tsukuba , Ibaraki 305-0044 , Japan.
Chem Sci. 2017 Sep 1;8(9):6679-6685. doi: 10.1039/c7sc03165c. Epub 2017 Aug 4.
Building on recent progress in the synthesis of functional porphyrins for a range of applications using the Cu-mediated azide-alkyne cycloaddition (CuAAC) reaction, we describe the active template CuAAC synthesis of interlocked triazole functionalised porphyrinoids in excellent yield. By synthesising interlocked analogues of previously studied porphyrin-corrole conjugates, we demonstrate that this approach gives access to rotaxanes in which the detailed electronic properties of the axle component are unchanged but whose steric properties are transformed by the mechanical "picket fence" provided by the threaded rings. Our results suggest that interlocked functionalised porphyrins, readily available using the AT-CuAAC approach, are sterically hindered scaffolds for the development of new catalysts and materials.
基于近期利用铜介导的叠氮-炔环加成（CuAAC）反应合成用于一系列应用的功能性卟啉的进展，我们描述了以优异产率通过活性模板CuAAC合成互锁的三唑官能化类卟啉。通过合成先前研究的卟啉-卟吩共轭物的互锁类似物，我们证明这种方法能够得到轮烷，其中轴组件的详细电子性质未变，但其空间性质因螺纹环提供的机械“栅栏”而改变。我们的结果表明，使用活性模板CuAAC方法易于获得的互锁功能化卟啉是用于开发新型催化剂和材料的空间受阻支架。
