Synthesis and properties of highly ordered polyacene derivatives using extended reactive molecules

2019 Fiscal Year Final Research Report

• Project/Area Number: 18K14227
• Research Category: Grant-in-Aid for Early-Career Scientists
• Allocation Type: Multi-year Fund
• Review Section: Basic Section 33020:Synthetic organic chemistry-related
• Research Institution: Tokushima Bunri University (2019); Kwansei Gakuin University (2018)
• Principal Investigator: Kitamura Kei 徳島文理大学, 薬学部, 助教 (00756695)
• Project Period (FY): 2018-04-01 – 2020-03-31
• Keywords: 多環芳香族化合物 / イソアセノフラン / ヘキサセン / π電子拡張 / キノイド構造 / 機能性分子 / 反応性分子

Outline of Final Research Achievements

Acenes are linearly-fused polycyclic aromatic hydrocarbons, which can serve as useful functional materials. Based on previously developed successive annulation of substituted isobenzofurans with aryne toward highly condensed aromatics, the synthesis of larger polyacenes by using π-extended isoacenofurans as novel quinoidal synthetic blocks was investigated. Isonaphthofuran or isoanthracenofuran, generated in situ by acidic treatment of the hydroxyketone precursors, underwent [4+2] cycloaddition with quinone. Further functionalization including the nucleophilic additions of alkynyllithium and reductive aromatization produced π-extended substituted hexacenes. The structural details by X-ray analysis as well as photophysical and electrochemical properties were studied.

Free Research Field

有機合成化学

Academic Significance and Societal Importance of the Research Achievements

π拡張したキノイド型反応性分子の合成的利用を図り，イソアセノフランを新規合成ブロックとする高次アセン化合物の迅速合成法を開発した。本手法はアセン構造をモチーフとするπ共役分子の合成法として柔軟性に優れている。また，縮環数の異なる様々な置換アセン誘導体を系統的に合成し，一連の化合物ライブラリーについて構造解析および物性評価が可能である。今後，アセンの特性を利用した機能性分子の開発が期待される。