Syntheses and Applications of High-ordered Iptycene Derivatives

2020 Fiscal Year Final Research Report

• Project/Area Number: 19K15546
• Research Category: Grant-in-Aid for Early-Career Scientists
• Allocation Type: Multi-year Fund
• Review Section: Basic Section 33010:Structural organic chemistry and physical organic chemistry-related
• Research Institution: Kwansei Gakuin University
• Principal Investigator: Jung Sunna 関西学院大学, 理工学部, 助教 (10781643)
• Project Period (FY): 2019-04-01 – 2021-03-31
• Keywords: イプチセン / イソベンゾフラン / ポリアセン / イソベンゾヘテロール / 一重項分裂

Outline of Final Research Achievements

Iptycenes, propeller-shaped molecules, are [2,2,2] bicyclic systems with fused aromatic rings showing unique electronic properties as well as molecular dynamics derived from their intriguing three dimensional structures. Although they draw great attention as potential organic materials, functionalization of iptycenes toward high-ordered molecular structures are limited. Herein, utilizing reactive species such as isobenzofuran, a novel iptycene building block was developed and applied to a synthesis of 3D pentacene, a highly condensed aromatic system. Moreover, propeller-shaped isobenzoheteroles were synthesized. The structural details of these molecules were described by X-ray analysis and photochemical properties including singlet fission were well examined.

Free Research Field

有機合成化学

Academic Significance and Societal Importance of the Research Achievements

イプチセンの合成ブロックとして、キノイド高反応性分子を三つ有するプロペラ型イソベンゾフランを独自に開発し、反応集積化により三方向に芳香族環が拡張された高次イプチセン類を高効率で合成した。本手法で得られる 3Dペンタセンは分子内電子相互作用により高収率の分子内一重項分裂が観測され、今後その励起三重項エネルギーを活用できると考えられる。また、イソベンゾフランの酸素原子を硫黄原子に変換することにより、プロペラ型ジフェニルイソベンゾチオフェンの合成も可能になり、基礎的な物性評価の結果、新たな機能性色素分子への開発が期待できる。