Structure Control of Open-chain Oligopyrroles Leading to Chirality-related Functions

2015 Fiscal Year Final Research Report

• Project/Area Number: 24550050
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Research Field: Organic chemistry
• Research Institution: Kobe University
• Principal Investigator: Setsune Jun-ichiro 神戸大学, 理学(系)研究科(研究院), 教授 (10117997)
• Project Period (FY): 2012-04-01 – 2016-03-31
• Keywords: らせん不斉 / オリゴピロール / ヘリケート

Outline of Final Research Achievements

This work aimed at creating new oligopyrrole helicates with high helical sense bias leading to chirality-related functions. The hexapyrrole-α,ω-dialdehyde was synthesized and easily converted into the dipalladium helicates of hexapyrrole-α,ω-diimines by using optically active amines. These helicates can take a couple of conformations, but the α,ω-diimine derived from (R)-1-cyclohexylethylamine induced P-helical closed C2 form in 85% diastereoselectivity. An appropriate choice of the substitution pattern in the 2,2’-bipyrrole unit resulted in full bias of P-helical sense. Introduction of 1,3- and 1,4-phenylene spacer into the 2,2’-bipyrrole unit also caused more than 95% diastereoselectivity of the one-handed helicate by using a variety of optically active amines. The one-handed hexapyrrole helicate underwent reversible one-electron redox at less positive potentials accompanied by the drastic changes of the strong CD signals at 600 - 800 nm.

Free Research Field

構造有機化学