4-Methoxy-1,3-thiazole based donor-acceptor dyes: Characterization, X-ray structure, DFT calculations and test as sensitizers for DSSC

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• 作者：Roberto Menzel^a ; Daniel Ogermann^b ; Stephan Kupfer^c ; Dieter Weiß ; ^a ; Helmar Gö ; rls^d ; Karl Kleinermanns^b ; ^{kleinermanns@uni-duesseldorf.de} ; Leticia Gonzá ; lez^c ; ^e ; ^{leticia.gonzalez@univie.ac.at} ; Rainer Beckert^a ; ^{c6bera@uni-jena.de}
• 关键词：4-Hydroxy-1 ; 3-thiazoles ; Double N-arylation ; DSSC ; DFT calculations ; Donor-蟺-acceptordyes ; X-ray structure
• 刊名：Dyes and Pigments
• 出版年：2012
• 期刊代码：31_01437208
• 类别：ms
• 出版时间：September, 2012
• 卷：94
• 期：3
• 页码：512-524
• 文件大小：1226 K

摘要

Four donor-(蟺-conjugated-bridge)-acceptor type dyes A-D were designed and synthesized. These new compounds use an unconventional 4-hydroxy-1,3-thiazole building block as an additional chromophore for light harvesting and to extend the 蟺-conjugated system of the molecules. The synthetic route involved a double N-arylation Hartwig-Buchwald reaction using Pd(dba)₂ as precatalyst and P(^tBu)₃ as ligand. Two different triarylamines and a 4-methoxyphenyl group were used as electron donor moieties. The electron acceptor (anchoring) group was 2-cyanoacrylic acid for all dyes, whereas the 蟺-spacer was聽varied and the influence was investigated. The dyes were thoroughly characterized using聽photophysical聽and electrochemical methods聽and by聽density functional theory calculations. Additionally, they were evaluated in nanocrystalline TiO₂-based dye-sensitized solar cells (DSSCs). The DSSCs were prepared with and without deoxycholic acid (DCA) as a co-adsorbent to inhibit dye aggregation. The efficiencies obtained were low for DSSCs fabricated without DCA, but were significantly improved for DCCS with co-adsorbed DCA. Additionally, the X-ray structure of dye D was obtained, demonstrating the stereochemistry and planar geometry of the molecule. The DSSC based on dye A showed an efficiency of 畏聽=聽1.70%(J_sc聽=聽4.49聽mA聽cm^鈭?, V_OC聽=聽0.61聽V, FF聽=聽0.62) under 100聽mW聽cm^鈭? simulated AM 1.5聽G solar irradiation compared to 畏聽=聽4.1%of the standard N₃ obtained under same conditions.