February 2, 2023
Faculty of Pharmacy, Keio University
A research group led by Professor Naoya Kumagai of the Faculty of Pharmacy, Keio University, has newly designed and established a chemical synthesis method for TEtraQuinoline (TEQ), a non-planar analog of porphyrin, which is a planar, nitrogen-containing macrocyclic molecule widely found in nature.
Porphyrin aligns four nitrogen atoms inside its cyclic structure and, by encapsulating various metal ions, is universally used in all living organisms as a functional molecule that drives a variety of chemical phenomena unattainable with only typical elements. Due to their broad catalytic functions, molecular transport capabilities, and molecular recognition abilities, porphyrin metal complexes have attracted attention as naturally derived, ultra-functional molecular units and are incorporated in diverse ways into a wide variety of artificial molecular materials. While functional enhancements that modify the skeletal structure of porphyrin itself have been extensively developed using organic synthetic chemistry, molecular designs that disrupt its planarity had not been created.
Against this backdrop, this research has led to the development of the new molecule TEQ, which achieves both the strategic non-planarization of a porphyrin-like skeleton and the ability to encapsulate metal ions. TEQ is a rigid, stereogenic C 2 -symmetric molecule. By introducing the concepts of steric factors and chirality to the chemistry of porphyrin metal complexes, this work presents an important first step and future prospects for the creation of more multidimensional functional molecules.
The results of this research were published in the online edition of the international academic journal "Journal of the American Chemical Society" on January 23, 2023 (US Eastern Time).
Please see below for the full press release.