Chiral stationary phases consisting of p-conjugated polymers bearing glucose-linked biphenyl units: Reversible switching of recognition abilities based on coil-to-helix transition

2016 Fiscal Year Final Research Report

• Project/Area Number: 26410129
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Research Field: Polymer chemistry
• Research Institution: Kanazawa University
• Principal Investigator: Ikai Tomoyuki 金沢大学, 物質化学系, 准教授 (90402495)
• Project Period (FY): 2014-04-01 – 2017-03-31
• Keywords: 共役高分子 / スイッチング / キラリティー / グルコース / 高次構造 / 光学分割 / コンホメーション / 軸不斉

Outline of Final Research Achievements

An optically active p-conjugated polymer (poly-1) consisting of alternating thieno[3,4-b]thiophene and glucose-linked biphenyl units was synthesized. We found that poly-1 undergoes a conformational transition between random-coil and helix in both solution and the solid state in response to the external solvent environment. Coated-type chiral stationary phases (CSPs) were prepared from both the random-coil and helical poly-1, and the influence of the polymer backbone structure on chiral recognition ability was evaluated. The two CSPs showed complementary resolution abilities. In addition, an immobilized-type CSP with universal solvent durability was also prepared using an alkyne-appended poly-1 analogue and an azide-functionalized silica gel. The resulting CSP displayed repeatable switching of the chiral recognition ability based on a coil-to-helix transition of the polymer backbone by alternate column treatment with common organic solvents, such as chloroform and acetonitrile.

Free Research Field

機能性高分子