利用碳氫鍵芳香環化反應高效率合成小分子有機半導體材料之末端基與其在染料敏化太陽能電池之應用;The End Groups for Small-Molecule Organic Semiconducting Materials: Synthetic Investigation and Photovoltaic Applications through Direct C-H Arylations

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Title:	利用碳氫鍵芳香環化反應高效率合成小分子有機半導體材料之末端基與其在染料敏化太陽能電池之應用;The End Groups for Small-Molecule Organic Semiconducting Materials: Synthetic Investigation and Photovoltaic Applications through Direct C-H Arylations
Authors:	盧德睿;Lu,Te-Jui
Contributors:	化學工程與材料工程學系
Keywords:	末端基;有機小分子;有機半導體材料;直接碳氫鍵芳香環化;染料敏化太陽能電池;End Groups;Organic Small-Molecule;Organic Semiconducting Materials;Direct C-H Arylations;dye-sensitized solar cell
Date:	2015-07-16
Issue Date:	2015-09-23 10:44:31 (UTC+8)
Publisher:	國立中央大學
Abstract:	小分子有機半導體材料中末端基是不可或缺的一部分，而傳統合成末端基的方法需較多且複雜的步驟。於本文中將介紹具有步驟經濟效益之策略來合成小分子有機半導體材料中之末端基，利用鈀催化直接碳氫鍵芳香環化反應，合成各式推電子 (Donor) 與拉電子 (Acceptor) 末端基，且此方法可將反應步驟從先前傳統人名反應中的四個步驟減少到與需一個步驟就可完成。首先需尋找最佳化的反應條件，經過了篩選各式溶劑、配位基與鹼後得到最佳化反應條件。為證明此條件的適用性，於此嘗試各種推電子基團 (Donor)、拉電子基團 (Acceptor) 與芳香雜環的變化且可成功合成各類型末端基，證實此反應條件廣闊的應用性。而末端基結構於小分子有機半導體材料中，常見應用於有機光伏電池 (OPVCs)、有機場效電晶體 (OFETs)、有機發光二極體 (OLEDs) 與染料敏化太陽能電池 (DSSCs)。本文中將合成之末端基應用於染料敏化太陽能電池 (DSSCs)，並展示了兩項新型D-π-A有機染料CYL-1與CYL-2之合成，並測得其能源轉換效率 (PCE) 為4.62-5.33 %。這項研究可給予材料科學家們新的思維，可利用更加便利，更少合成步驟的方法合成具功能性的有機小分子。 ;A Pd-catalyzed C-H (hetero)arylation methodology is well optimized for the efficient synthesis of various useful end group required in small-molecule organic materials. This report provides a broad substrate scope of target end groups ranging from donor-type through acceptor-type to hybrid-type molecules. For applications in dye-sensitized solar cells (DSSCs), we demonstrates that two D--A type new organic sensitizers (CYL-1, CYL-2) can be step-economically synthesized via sequential C-H arylations using our facilely obtained end groups. CYL-1 and CYL-2 give a Voc of 0.63~0.69 V, a Jsc of 10.31~11.07 mA/cm2, and a FF of 69.9~70.8%, which corresponds to an overall power conversion efficiency (PCE) of 4.62~5.33%. This work is expected to become a practical synthetic alternative aiming at guiding material scientists to access small-molecule materials of interest with less synthetic transformations.
Appears in Collections:	[National Central University Department of Chemical & Materials Engineering] Electronic Thesis & Dissertation

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