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| 題名: | 由5-炔基-1,2,3-三嗪進行雜環骨架編輯以建構官能化噻吩與硒吩;Heterocyclic Skeletal Editing of 5-Alkynyl-1,2,3-Triazines toward Functionalized Thiophenes and Selenophenes |
| 作者: | 張家豪;Chang, Chia-Hao |
| 貢獻者: | 化學學系 |
| 關鍵詞: | 烯炔;環化異構化反應;三嗪;噻吩;硒吩;Enynes;Cycloisomerization reaction;Triazines;Thiophenes;Selenophenes |
| 日期: | 2025-08-21 |
| 上傳時間: | 2025-10-17 11:37:36 (UTC+8) |
| 出版者: | 國立中央大學 |
| 摘要: | 五員芳香雜環化合物在藥物化學、農業化學、材料科學與半導體等領域中佔有重要的地位，特別是噻吩與硒吩類衍生物，由於其優異的電子性質與結構可調性，廣泛應用於有機場效電晶體、有機太陽能電池、有機發光二極體等元件中。傳統建構此類雜環的方法多依賴過渡金屬催化、嚴苛的反應條件或侷限於特定的底物。本論文中，我們提出一種溫和、操作簡便且具環境永續概念的合成策略，能有效建構官能化噻吩與硒吩骨架。該方法結合骨架編輯的概念，以5-取代炔基-1,2,3-三嗪為起始物，分別以廉價的硫化鈉與新鮮製備的硒化鈉，作為硫與硒的來源，透過親核加成反應破壞三嗪芳香性後，脫去氮氣並進行環化異構化反應，成功合成多種具取代基之噻吩與硒吩產物。特別的是，該反應可在室溫以有機溶劑與水共溶劑下進行反應，且無需額外過渡金屬催化劑或嚴苛的反應條件。此方法展現出優異的官能基耐受性、廣泛的底物適用性以及良好至優異的產率，反應不僅具備原子經濟性，亦契合綠色化學原則，為雜環分子的骨架編輯與建構提供了嶄新方向。;Five-membered aromatic heterocycles play a significant role in pharmaceutical chemistry, agrochemistry, materials science, and semiconductor technology. In particular, thiophene and selenophene derivatives, due to their excellent electronic properties and structural tunability, have been widely utilized in organic field-effect transistors, organic solar cells, and organic light-emitting diodes. Traditional methods for constructing these heterocycles often rely on transition metal catalysis, harsh reaction conditions, and are limited to substrates that are not readily available. In this study, we present a mild, operationally simple, and environmentally sustainable synthetic strategy for the efficient construction of functionalized thiophene and selenophene frameworks. By incorporating the concept of skeletal editing, this method utilizes 5-substituted alkynyl-1,2,3-triazines as starting materials and employs readily available sodium sulfide and freshly prepared sodium selenide as sources of sulfur and selenium, respectively. This process involves dearomatization of 1,2,3-triazine, followed by the in situ loss of nitrogen and subsequent cycloisomerization, resulting in a variety of substituted thiophene and selenophene derivatives. Notably, the reaction occurs under mild conditions in a mixture of an organic solvent and water, eliminating the need for additional transition-metal catalysts or harsh conditions. This green protocol presents several advantages, including excellent functional group tolerance, a broad substrate scope, and good to excellent yields. Additionally, it demonstrates high atom economy and aligns well with the principles of green chemistry, providing a novel and practical platform for heterocyclic skeletal editing and structural diversification. |
| 顯示於類別: | [化學研究所] 博碩士論文
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