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    請使用永久網址來引用或連結此文件: https://ir.lib.ncu.edu.tw/handle/987654321/110028


    題名: 新型有機藍色染料分子之設計、合成、性質探討與染料敏化太陽能電池應用;新型有機藍色染料分子之設計、合成、性質探討與染料敏化太陽能電池應用
    作者: 徐嘉謙;Hsu, Jia Chian
    貢獻者: 化學學系
    關鍵詞: 新型有機藍色染料;太陽能電池應用;分子設計;分子合成;分子性質探討;染料敏化太陽能電池;Novel organic blue dyes;BIPV;Molecular Design;Molecular Synthesis;Molecular Characterization;DSCs
    日期: 2026-08-03
    上傳時間: 2026-10-20 15:05:38 (UTC+8)
    出版者: 國立中央大學
    摘要: 近年來建築整合式光伏(Building-Integrated Photovoltaics,BIPV)材料已成為可再生能源技術的重要發展方向,其中染料敏化太陽能電池(Dye-sensitized solar cells,DSCs)以其半透光度及色彩多樣性,被視為BIPV應用的理想技術,然而,藍色染料的開發一直是DSCs色彩調控中的關鍵挑戰之一。目前常見的藍色有機分子染料包含Squaraine (SQ)和Diketopyrrolopyrrole (DPP),以及近年新發展的多環芳香烴(PAH)分子等,其結構修飾雖能優化分子的吸光能力與穩定性,卻常因合成繁瑣、產率偏低及溶解度不佳而受限,相較之下,本研究所聚焦的DASAs (Donor-Acceptor Stenhouse Adducts)有機分子,是一種由電子供體(Donor)、電子受體(Acceptor)和三烯醇-烯醇(Trienol−Enol)連接而成的新型光響應化合物,此類分子以合成簡易及溫和條件使其具備優勢,本研究的目標產物CYC-111以第三代DASAs的電子受體(1,3-indandione)為基礎,額外連結羧酸官能基,並搭配2-methylindoline作為電子供體,同時合成了CYC-111-ester以剖析羧酸官能基與酯基對於DASAs分子性質之影響程度,另外,也與以diethylamine作為電子供體之CYC-110-ester與CYC-110一同比較其光學性質。考量合成簡易性與分子穩定性,且為避免合成DASAs合成中triene結構引發的E/Z異構物問題,另以thienylene為π橋,連接電子供體diphenylamine,並進一步在電子受體端引入強拉電子基dicyanomethylene,設計出結構互為同分異構物之新型藍色染料CYC-113與CYC-114。吸收光譜顯示,CYC-111系列其最大吸收波長位於~650 nm,較前代 CYC-110系列位於~600 nm表現明顯紅移,且吸光範圍得以涵蓋至近紅外光波段(~735 nm),另外,CYC-113與CYC-114 其最大吸收波長則位於580~603 nm;吸光範圍涵蓋至~700 nm, 因此CYC-111、CYC-113及CYC-114敏化元件皆呈現深邃的藍色,而CYC-110則為深紫色。初步測試結果顯示,元件的光電轉換效率分別達到CYC-110:0.37%;CYC-111:0.62%;CYC-113:2.27%;CYC-114:1.84%。;Abstract
    In recent years, Building-Integrated Photovoltaics (BIPV) materials have become an important development direction for renewable energy technologies. Among them, dye-sensitized solar cells (DSCs) are considered an ideal technology for BIPV applications due to their semi-transparency and color diversity. However, the development of blue dyes has consistently been one of the key challenges in the color regulation of DSCs. Currently, common blue organic molecular dyes include squaraine (SQ) and diketopyrrolopyrrole (DPP), as well as recently developed polycyclic aromatic hydrocarbon (PAH) molecules. Although their structural modifications can optimize the light-absorption capability and stability of the molecules, they are often limited by tedious synthesis, low yields, and poor solubility. In contrast, the Donor-Acceptor Stenhouse Adducts (DASAs) organic molecules focused on in this study are a novel type of photoresponsive compounds composed of an electron donor, an electron acceptor, and a trienol-enol linkage. This class of molecules possesses advantages due to their facile synthesis and mild reaction conditions. Based on the electron acceptor (1,3-indandione) of third-generation DASAs, the target product of this study, CYC-111, is additionally linked with a carboxylic acid functional group and paired with 2-methylindoline as the electron donor. Concurrently, CYC-111-ester was synthesized to analyze the degree of influence of the carboxylic acid functional group versus the ester group on the molecular properties of DASAs. Furthermore, its optical properties were compared with CYC-110-ester and CYC-110, which utilize diethylamine as the electron donor.
    Considering synthesis simplicity and molecular stability, and to avoid the E/Z isomerism issues induced by the triene structure during DASA synthesis, thienylene was alternatively utilized as a π-bridge to connect the electron-donating diphenylamine. Moreover, a strong electron-withdrawing dicyanomethylene group was introduced at the electron acceptor end to design novel blue dyes, CYC-113 and CYC-114, whose structures are isomers of each other. Absorption spectra show that the maximum absorption wavelength of the CYC-111 series is located at ~650 nm, exhibiting a significant red-shift compared with the previous generation CYC-110 series located at ~600 nm, and the light-absorption range successfully extends into the near-infrared region (~735 nm). Additionally, the maximum absorption wavelengths of CYC-113 and CYC-114 are located between 580 and 603 nm, with the light-absorption range extending to ~700 nm. Consequently, the CYC-111, CYC-113, and CYC-114 sensitized devices all display a deep blue color, whereas CYC-110 appears deep purple. Preliminary test results indicate that the power conversion efficiencies of the devices reach 0.37% for CYC-110, 0.62% for CYC-111, 2.27% for CYC-113, and 1.84% for CYC-114, respectively.
    顯示於類別:[化學研究所] 博碩士論文

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