研究生: |
鄭玉麒 Yu-chi Cheng |
---|---|
論文名稱: |
新型含薰香素基團之光敏化有機太陽能電池染料(4-氧-5-{5-[2-(1,1,6,6-四甲基-10-氧-2,3,5,6-四氫-1H,4H,10H-11-氧-3a-吖-苯駢[de]蒽-9-基)-苯駢-6-基]- 噻吩噻唑-2-基亞甲基}-2-硫酮-噻唑-3-基)-乙酸之合成與性質研究 Synthesis and Characterization of Coumarin-based Organic Dye (4-Oxo-5-{5-[2-(1,1,6,6-tetramethyl-10-oxo-2,3,5,6-tetrahydro-1H,4H,10H-11-oxa-3a-aza-benzo[de]anthracen-9-yl)-benzothiazol-6-yl]-thiophen-2-ylmethylene}-2-thioxo-thiazolidin-3-yl)-acetic Acid Having Benzothiazol Moiety for Organic Dye-Sensitized Solar Cell |
指導教授: |
廖本瑞
Ben-Ruey Liaw |
口試委員: |
曾文祺
Wen-Chi Tseng 黃炳綜 Ping-Tsung Huang |
學位類別: |
碩士 Master |
系所名稱: |
工程學院 - 化學工程系 Department of Chemical Engineering |
論文出版年: | 2008 |
畢業學年度: | 96 |
語文別: | 中文 |
論文頁數: | 75 |
中文關鍵詞: | 有機染料敏化太陽能電池 |
外文關鍵詞: | Dye-Sensitized Solar Cell |
相關次數: | 點閱:367 下載:1 |
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本次研究為合成新型含薰草素基團之有機染料並研究其光學性質,同時使染料應用在有機染料敏化太陽能電池上。
新型含薰草素基團之有機染料重要的步驟如schemeΙ所示,由2-胺基-5-溴-苯硫(3) 3,3,3-三乙氧丙酸乙酯(5)在溶劑acetic acid 及 T HF下進行縮合反應得(6-溴-苯駢-2-基)-乙酸乙酯(6),接續著8-羥基-1,1,7,7-三甲基-2,3,6,7-四氫-1H,5H,必啶[3,2,1-ij]喹林-9-梭醛(9) 進行縮合反應得9-(6-溴-苯駢-2-基)-1,1,6,6-四甲基-2,3,5,6-四氫-1H,4H-11-氧-3a-吖-苯駢[de]蒽-10-酮(10),9-(6-溴-苯駢-2-基)-1,1,6,6-四甲基-2,3,5,6-四氫-1H,4H-11-氧-3a-吖-苯駢[de]蒽-10-酮(10)及2-噻吩硼酸在Pd(PPh3)4及K2CO3下進行Suzuki coupling reaction得1,1,6,6-四甲基-9-(6-噻吩-2-基-苯駢-2-基)-2,3,5,6-四氫-1H,4H-11-氧-3a-吖-苯駢[de]蒽-10-酮(12),1,1, 6,6-四甲基-9-(6-噻吩-2-基-苯駢-2-基)-2,3,5,6-四氫-1H,4H-11-氧-3a-吖-苯駢[de]蒽-10-酮(12)進行Vilsmeyer-Haack reacti on可得5-[2-(1,1,6,6-四甲基-10-氧-2,3,5,6-四氫-1H,4H,10H-11-氧-3a-吖-苯駢[de]蒽-9-基)-3H-吲哚-5基]-噻吩-2-carbaldehyde (13),5-[2-(1, 1,6,6-四甲基-10-氧-2,3,5,6-四氫-1H,4H,10H-11-氧-3a-吖-苯駢[de]蒽-9 -基)-3H-吲哚-5基]-噻吩-2- carbaldehyde (13)、Rhodanine-N-acetic ac id、piperidine在酒精溶液下迴流進行反應24小時,結束反應再以管柱層析法純化沉澱物得含薰草素染料(4-氧-5-{5-[2 - (1,1,6,6-四甲基-10-氧-2,3,5,6-四氫-1H,4H,10H-11-氧-3a-吖-苯駢[de]蒽-9-基)-苯駢-6-基]- 噻吩噻唑-2-基亞甲基}-2-硫硐-噻唑-3-基)-乙酸(14) 深咖啡色固體。
AM1.5 100mW/cm2模擬太陽光入射量測所得光電轉換效率(η%)為0.475%,Isc(Short Circuit Current)為0.403mA,開環電壓Voc(Open Circuit Voltage)為0.502V,填充因子(FF)為0.587。
初步的研究結果顯示含薰草素染料運用在應用在有機染料敏化太陽能電池上是相當具有發展性。
We reported here on the synthesis and photophysical properties of a no vel coumarin-based organic dye (14) as well as its application dye-sensiti zed nanocrystalline TiO2 solar cells (DSSCs).
The key step of the synthesis of new coumarin-based organic dye(14)for dye-sensitized solar cell as shown in scheme 1 ,is condensation reacti on of 2-Amino-5-bromobenzenethiol (3) and 3,3,3- triethoxypropionic ethyl ester (5) to give the corresponding (6-Bromo-benzothiazol-2-yl) - ac etic acid ethyl ester (6) in the presence of acetic acid and THF as solven t .Subsequent condensation with 8-hydroxy-1,1,7,7–tetramethyl -2, 3, 6,7 -tetrahydro-1H,5H-pyrido[3,2,1-ij]quinoline-9-carbaldehyde (9) gave 9- (6-Bromo-benzothiazol-2-yl)-1,1,6,6-tetramethyl -2, 3, 5, 6– tetrahydro- 1H,4H-11-oxa-3a-aza-benzo[de]anthracen-10-one(10).Suzuki coupling reaction of the intermediate (10) with 2-thienyl-boronic acid in the presence of Pd(PPh3)4 and K2CO3 gave 1,1,6,6-tetramethyl-9 -(6-thiophen -2–yl-benzothiazol-2-yl)-2,3,5,6-tetrahydro-1H,4H-11-oxa-3a-aza-benzo[de]anthracen-10-one(12). 5-[2-(1,1,6, 6-tetramethy l-10-oxo -2,3, 5,6 – tetrhydro-1H,4H,10H-11 -oxa-3a-a za-benzo[de] anthracen-9-yl) -3H – indol -5-yl]-thiophene-2-carbaldehyde (13) was synthesized from (12) by the Vilsmeyer-Haack reaction .An ethanolic solution including (13) and rhodanine- N-acetic acid was refluxed in the presence of piperidine for 24h.Purificat ion of the resulting precipitates by column chromatography to give deep b rown solids of the coumarin-based dye, (4-oxo -5-{5-[2 -(1,1,6,6- tetra methyl-10-oxo-2,3,5,6 -tetrahydro- 1H,4H,10H-11–oxa -3a-aza-benzo[de]anthracen- 9-yl) -benzothiazol-6-yl] –thiophen -2- ylmethylene}-2-thioxo-thiazolidin-3-yl) acetic acid(14).
A solar-energy-to-electricity conversion efficiency of 0.475% was attained under AM 1.5 irradiation (100mW/cm2) it’s a Short Circuit Current density (Isc) of 0.403mA,an Open Circuit Voltage (Voc) of 0.502V,and a fill factor (FF) of 0.587.
This preliminary work suggests that the molecular-designed coumarin dye is promising in the application of DSSCS.
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