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Optical and photovoltaic properties of thieno[3,2-b]thiophene-based push–pull organic dyes with different anchoring groups for dye-sensitized solar cells
The effect of anchoring groups on the optical and electrochemical properties of triphenylamine-thienothiophenes, and on the photovoltaic performance of DSSCs photosensitized with the prepared dyes, was studied using newly synthesized compounds with cyanoacetic acid or rhodanine-3-acetic acid groups. Precursor aldehydes were synthesized through Suzuki cross-coupling, whereas Knoevenagel condensation of these with 2-cyanoacetic acid or rhodanine-3-acetic acid afforded the final push–pull dyes. A comprehensive photophysical study was performed in solution and in the solid state. The femtosecond time-resolved transient absorption spectra for the synthesized dyes were obtained following photoexcitation in solution and for the dyes adsorbed to TiO2 mesoporous films. Information on conformation, electronic structure, and electron distribution was obtained by density functional theory (DFT) and time-dependent DFT calculations. Triphenylamine–thienothiophene functionalized with a cyanoacetic acid anchoring group displayed the highest conversion efficiency (3.68%) as the dye sensitizer in nanocrystalline TiO2 solar cells. Coadsorption studies were performed for this dye with the ruthenium-based N719 dye, and they showed dye power conversion efficiencies enhanced by 20–64%. The best cell performance obtained with the coadsorbed N719 and cyanoacetic dye showed an efficiency of 6.05%. ; The authors thank Fundacao para a Ciencia e Tecnologia (FCT) for PhD grants to S.S.M.F. (SFRH/BD/87786/2012) and M.C.R.C. (SFRH/BD/78037/2011) and postdoctoral grants to L.L.G.J. (SFRH/BPD/97026/2013) and J.P. (SFRH/BPD/108469/2015). The authors also thank FEDER-COMPETE for the financial support through the CQ/UM PEst-C/QUI/UI0686/2013 (FCOMP-01-0124-FEDER-037302). The NMR spectrometer Bruker AVANCE III 400 is part of the National NMR Network and was purchased within the framework of the National Program for Scientific Re-equipment, contract REDE/1517/RMN/2005 with funds from POCI 2010 (FEDER) and FCT. The group in Coimbra are grateful for funding from "Centro de Quimica de Coimbra," which is supported by the Fundacao para a Ciencia e a Tecnologia (FCT), Portuguese Agency for Scientific Research, through the programs UID/QUI/UI0313/2013 and COMPETE. The authors also thank the Laboratory for Advanced Computing at the University of Coimbra for providing computing resources that have contributed to the research results reported in this paper (URL http://www.lca.uc.pt). This work was performed under the project "SunStorage. harvesting and storage of solar energy,"with reference POCI-01-0145-FEDER-016387, funded by the European Regional Development Fund (ERDF), through COMPETE 2020. Operational Programme for Competitiveness and Internationalization (OPCI), and by national funds through FCT. The research leading to these results has received funding from Laserlab-Europe (grant agreement no. 284464, EC's Seventh Framework Programme). A.I.P. would like to acknowledge the European Commission through the Seventh Framework Programme, the Specific Programme "Ideas" of the European Research Council for research and technological development as part of an Advanced Grant under grant agreement no. 321315, which also partially funded this work. The authors would also like to acknowledge L. Andrade and I. Mesquita for their valuable contribution for the article. ; info:eu-repo/semantics/publishedVersion
Optical and photovoltaic properties of thieno[3,2-b]thiophene-based push–pull organic dyes with different anchoring groups for dye-sensitized solar cells
The effect of anchoring groups on the optical and electrochemical properties of triphenylamine-thienothiophenes, and on the photovoltaic performance of DSSCs photosensitized with the prepared dyes, was studied using newly synthesized compounds with cyanoacetic acid or rhodanine-3-acetic acid groups. Precursor aldehydes were synthesized through Suzuki cross-coupling, whereas Knoevenagel condensation of these with 2-cyanoacetic acid or rhodanine-3-acetic acid afforded the final push–pull dyes. A comprehensive photophysical study was performed in solution and in the solid state. The femtosecond time-resolved transient absorption spectra for the synthesized dyes were obtained following photoexcitation in solution and for the dyes adsorbed to TiO2 mesoporous films. Information on conformation, electronic structure, and electron distribution was obtained by density functional theory (DFT) and time-dependent DFT calculations. Triphenylamine–thienothiophene functionalized with a cyanoacetic acid anchoring group displayed the highest conversion efficiency (3.68%) as the dye sensitizer in nanocrystalline TiO2 solar cells. Coadsorption studies were performed for this dye with the ruthenium-based N719 dye, and they showed dye power conversion efficiencies enhanced by 20–64%. The best cell performance obtained with the coadsorbed N719 and cyanoacetic dye showed an efficiency of 6.05%. ; The authors thank Fundacao para a Ciencia e Tecnologia (FCT) for PhD grants to S.S.M.F. (SFRH/BD/87786/2012) and M.C.R.C. (SFRH/BD/78037/2011) and postdoctoral grants to L.L.G.J. (SFRH/BPD/97026/2013) and J.P. (SFRH/BPD/108469/2015). The authors also thank FEDER-COMPETE for the financial support through the CQ/UM PEst-C/QUI/UI0686/2013 (FCOMP-01-0124-FEDER-037302). The NMR spectrometer Bruker AVANCE III 400 is part of the National NMR Network and was purchased within the framework of the National Program for Scientific Re-equipment, contract REDE/1517/RMN/2005 with funds from POCI 2010 (FEDER) and FCT. The group in Coimbra are grateful for funding from "Centro de Quimica de Coimbra," which is supported by the Fundacao para a Ciencia e a Tecnologia (FCT), Portuguese Agency for Scientific Research, through the programs UID/QUI/UI0313/2013 and COMPETE. The authors also thank the Laboratory for Advanced Computing at the University of Coimbra for providing computing resources that have contributed to the research results reported in this paper (URL http://www.lca.uc.pt). This work was performed under the project "SunStorage. harvesting and storage of solar energy,"with reference POCI-01-0145-FEDER-016387, funded by the European Regional Development Fund (ERDF), through COMPETE 2020. Operational Programme for Competitiveness and Internationalization (OPCI), and by national funds through FCT. The research leading to these results has received funding from Laserlab-Europe (grant agreement no. 284464, EC's Seventh Framework Programme). A.I.P. would like to acknowledge the European Commission through the Seventh Framework Programme, the Specific Programme "Ideas" of the European Research Council for research and technological development as part of an Advanced Grant under grant agreement no. 321315, which also partially funded this work. The authors would also like to acknowledge L. Andrade and I. Mesquita for their valuable contribution for the article. ; info:eu-repo/semantics/publishedVersion
Optical and photovoltaic properties of thieno[3,2-b]thiophene-based push–pull organic dyes with different anchoring groups for dye-sensitized solar cells
Fernandes, Sara Sofia Marques (author) / Castro, M. Cidália R. (author) / Pereira, Ana Isabel (author) / Mendes, Adélio (author) / Serpa, Carlos (author) / Pina, João (author) / Justino, Licinia L. G. (author) / Burrows, Hugh D. (author) / Raposo, M. Manuela M. (author)
2017-12-01
doi:10.1021/acsomega.7b01195
Article (Journal)
Electronic Resource
English
UV-visible , Photovoltaic Properties , Science & Technology , Fluorescence , synthesis , Density functional theory (DFT) and time-dependent DFT calculations , Triphenylamine , Femtosecond time-resolved transient absorption spectra , Thieno[3,2-b]thiophene , Dye-Sensitized Solar Cells (DSSCs) , Ciências Naturais::Ciências Químicas
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