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| 題名: | 新型S,N-駢七芳香雜環化合物之高效率合成與其在反式鈣鈦礦太陽能電池應用之研究;Study on Efficient Synthesis of New S,N-Heteroheptacene for Applications in Inverted Perovskite Solar Cells |
| 作者: | 蔡宗晉;Cai, Zong-Jin |
| 貢獻者: | 化學工程與材料工程學系 |
| 關鍵詞: | S,N-駢七芳香雜環;二噻吩并吡咯;碳-氫鍵活化;S,N-heteroheptacene;dithienopyrrole;C-H bond activation |
| 日期: | 2025-08-04 |
| 上傳時間: | 2025-10-17 11:31:51 (UTC+8) |
| 出版者: | 國立中央大學 |
| 摘要: | 駢苯(acene)是一種具有多個苯環稠合(fused)的化合物，其中駢五苯(pentacene)因其具有良好的電子遷移率，在有機半導體材料領域於數年前已成為備受矚目的研究項目之一。然而，駢五苯目前無法廣泛地應用，其原因歸咎於該分子的合成路徑較為複雜，且具有一定程度的不穩定性，這些因素導致駢五苯在合成化學以及材料應用領域受到限制。相比駢苯，駢芳香雜環(heteroacene)的穩定性較高，且分子的合成相對簡單，因此，駢芳香雜環的相關研究已逐漸成為許多團隊的研究重心。其中，駢噻吩(thienoacene)或芳香雜環交替相駢的新型小分子(S,X-heteroacene; X = S, N, Se)擁有高度平面性、熱穩定性等性質，如今有許多團隊正致力於將上述分子與相關衍生物應用到有機光電材料之中。
二噻吩并吡咯(dithienopyrrole : DTP)屬於駢芳香雜環的一種，其應用在有機光電材料領域的相關文獻頗為常見。然而，以該分子作為核心分子所製作的駢七芳香雜環(heteroheptacene)之相關報導卻是相當稀少。因此，本篇工作將著重在挑戰合成以二噻吩并吡咯作為核心小分子，由三員環相駢延伸至穩定、具有溶解度之噻吩與吡咯環交替相駢的S,N-駢七芳香雜環新型小分子。
在合成設計中，π共軛延伸步驟，本團隊之合成方法採用低成本、省步驟的直接碳-氫鍵活化/芳香環化，取代文獻中經常使用的根岸耦合反應(Negishi coupling reaction)。除此之外，關鍵的閉環反應，本團隊使用過度金屬催化的碳-硫鍵或碳-氮鍵生成反應，實現可調控噻吩/吡咯環數量之效果，進而得到五種新型小分子(JXH01, ZJC01-ZJC04 )。在應用端，本團隊將上述提到的五種新型駢七芳香雜環分子導入反式鈣鈦礦太陽能電池元件之電洞傳輸層，並展示出不錯的光電轉換效率。
;Acene are a class of compounds composed of linearly fused benzene rings, among which pentacene has emerged as a prominent research focus in the field of organic semiconductors due to its excellent charge carrier mobility. However, the practical application of pentacene remains limited due to its complex synthetic routes and intrinsic instability, which restrict its development in both synthetic chemistry and materials science. In contrast, heteroacene, composed of fused aromatic rings with heteroatoms, offer better stability and are easier to synthesize. Research on heteroacene has surged in recent years. Among them, thienoacene and newly designed fused small molecules with alternating aromatic heterocycles (S,X-heteroacene; X = S, N, Se) possess characteristics such as high planarity and thermal stability, making them promising candidates for use in organic optoelectronic materials.
Dithienopyrrole (DTP), a type of heteroacene, has been widely reported in the field of organic optoelectronic materials. However, reports on heteroheptacene constructed with DTP as the central core remain quite rare. Therefore, this work focuses on the challenging synthesis of novel, stable, and soluble S,N-heteroheptacene small molecules featuring alternating fused thiophene and pyrrole rings, starting from DTP as the core unit and extending the conjugation from a tricyclic framework.
For the key π-conjugated extension step, our synthetic strategy employs a cost-effective and step-economical direct C-H activation/aromatization method, instead of the commonly used Negishi coupling reaction. Additionally, the crucial ring-closing reactions are achieved via transition metal-catalyzed C-S or C-N bond formation, enabling precise control over the number and sequence of thiophene and pyrrole units. This strategy successfully yields five novel heteroheptacene molecules (JXH01, ZJC01-ZJC04). In terms of application, these newly synthesized heteroheptacene derivatives are incorporated as hole-transporting layers in inverted perovskite solar cells, where they demonstrate promising power conversion efficiencies. |
| 顯示於類別: | [化學工程與材料工程研究所] 博碩士論文
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