含 Thieno[3.4-c]pyrrole-4.6-dione 小分子衍生物之合成及其在光伏打電池之應用

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题名:	含 Thieno[3.4-c]pyrrole-4.6-dione 小分子衍生物之合成及其在光伏打電池之應用 Thieno[3.4-c]pyrrole-4.6-dione-based derivatives and their application for organic photovoltaics
作者:	邱羿翰 Chiu, Yi-Han
贡献者:	化學系應用化學碩士班
关键词:	光伏打電池 Thieno[3.4-c]pyrrole-4.6-dione organic photovoltaics
日期:	2013-06
上传时间:	2013-10-03 14:18:59 (UTC+8)
摘要:	在本論文研究中，我們藉由Gewald 反應、Stille偶合反應、Kumada偶合反應、Sandmeyer 反應以及Ullmann 反應等化學方法，合成出以3,3'-dibromo-5,5'- bis(2-ethylhexyl)-4H,4'H-[1,1'-bi(cyclopenta[c]thiophene)]-4,4',6,6'(5H,5'H)-tetraone (Br-TPD) 單元作為電子受體（electron acceptor），3,3'雙取代之吩噻嗪（phenothiazine）、咔唑（carbazole）或三苯胺（triphenylamine）作為電子予體（electron donor），以及以噻吩（thiophene）作為共軛架橋（spacer）所組成的一系列染料CH1、CH2、CH3和CH4。　　藉由循環伏安法（cyclic voltammetry）、差式脈衝伏安法（differential pulse voltammetry）、光電子光譜儀(AC−2)以及可見-紫外光光譜儀（UV-Vis absorption spectra），我們可以分別測得化合物在溶液狀態下的HOMO及LUMO能階電位與薄膜狀態下的HOMO能階，以及其光收成的能力。由於電子予體至電子受體間的電荷轉移，使得化合物的吸收範圍可達600 nm，並有不錯的消光係數(3.3700 −5.5300 M-1cm-1)。此系列化合物可作為有機光伏打太陽能電池（Organic Photovoltaic Cell，OPV）之p-型光敏染料，搭配PCBM混摻之體異質介面有機太陽能電池之光電轉換效率為0.10−1.4％。 Gewald reaction, Stille coupling reaction, Kumada coupling reaction, Sandmeyer reaction and the Ullmann reaction were used to synthesize a series of dyes CH1, CH2, CH3 and CH4 composed of a 3,3’-disubsituted 5,5'-bis(2-ethylhexyl)- 4H,4'H-[1,1'-bi(cyclopenta[c]thiophene)]-4,4',6,6'(5H,5'H)-tetraone (Br-TPD) units as the core, phenothiazine, carbazole, triphenylamine as the peripheral electron donor, and thiophene units as the bridge (spacer). Cyclic voltammetry, differential pulse voltammetry, and AC-2 and UV-Vis absorption spectra were used to estimate the HOMO and LUMO energies of the compounds in the solution state and the HOMO energy in the film state, respectively. The light harvesting ability of the compounds was judged from The UV-Vis absorption spectra. The strong charge transfer between the donor and acceptor results in long wavelength absorptions extending to 600 nm and with large extinction coefficients (3.3700−5.5300 M-1cm-1). The compounds can be used as the p-type sensitizers of organic photovoltaic cells. Bulk heterojunction type cells from the blend of the compounds and PCBM have conversion efficiencies ranging from 0.10% to 1.4%.
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