Simple BODIPY dyes as suitable electron-donors for organic bulk heterojunction photovoltaic cells

被引:23
作者
Aguiar, Antonio [1 ]
Farinhas, Joana [2 ]
da Silva, Wanderson [1 ]
Susano, Maria [3 ]
Silva, Manuela Ramos [3 ]
Alcacer, Luis [2 ]
Kumar, Santosh [1 ]
Brett, Christopher M. A. [1 ]
Morgado, Jorge [2 ,4 ]
Sobral, Abilio J. F. N. [1 ]
机构
[1] Univ Coimbra, FCTUC, Chem Dept, P-3004535 Coimbra, Portugal
[2] Inst Super Tecn, Inst Telecomunicacoes, Av Rovisco Pais 1, P-1049001 Lisbon, Portugal
[3] Univ Coimbra, Dept Phys, CFisUC, P-3004516 Coimbra, Portugal
[4] Univ Lisbon, Inst Super Tecn, Dept Bioengn, Av Rovisco Pais 1, P-1049001 Lisbon, Portugal
关键词
BODIPY dyes; Small molecules; Optoelectronic properties; Organic photovoltaic cells; Photovoltaic performance; SOLAR-CELLS; PERFORMANCE; FLUORESCENT; DESIGN; PROBES; SERIES;
D O I
10.1016/j.dyepig.2019.107842
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
In this work we present the synthesis and characterization (including the report of two new crystal structures) of a series of meso-substituted boron-dipyrromethene (BODIPY) molecules. With an accessible synthesis, these simple BODIPYs have characteristics that par with those BODIPY's having more complex structures, what makes them very interesting materials for industrial production. The photovoltaic performance of the synthesized BODIPY's was evaluated in bulk heterojunction organic solar cells, where they were used as electron-donors. We found that the presence of electron-withdrawing groups has a detrimental effect on the photovoltaic performance, while the meso-free structure shows an improved efficiency in comparison with the meso-substituted BODIPYs. We also studied the origin of the meso-unsubstituted derivative, elucidating at least one of its formation processes, which can open a new way of BODIPY synthesis.
引用
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页数:11
相关论文
共 39 条
[1]  
[Anonymous], 2003, SAINT PLUS DATA REDU
[2]   Double-tailed long chain BODIPYs - Synthesis, characterization and preliminary studies on their use as lipid fluorescence probes [J].
Arranja, Claudia T. ;
Aguiar, Antonio ;
Encarnacao, Telma ;
Fonseca, Sofia M. ;
Justino, Licinia L. G. ;
Castro, Ricardo A. E. ;
Benniston, Andrew ;
Harriman, Anthony ;
Burrows, Hugh D. ;
Sobral, Abilio J. F. N. .
JOURNAL OF MOLECULAR STRUCTURE, 2017, 1146 :62-69
[3]   Functionalized and partially or differentially bridged resorcin[4]arene cavitands: Synthesis and solid-state structures [J].
Azov, VA ;
Skinner, PJ ;
Yamakoshi, Y ;
Seiler, P ;
Gramlich, V ;
Diederich, F .
HELVETICA CHIMICA ACTA, 2003, 86 (11) :3648-3670
[4]   Synthesis and photo-physical properties of a series of BODIPY dyes [J].
Banfi, Stefano ;
Nasini, Gianluca ;
Zaza, Stefano ;
Caruso, Enrico .
TETRAHEDRON, 2013, 69 (24) :4845-4856
[5]   Redox-controlled fluorescence modulation in a BODIPY-quinone dyad [J].
Benniston, Andrew C. ;
Copley, Graeme ;
Elliott, Kristopher J. ;
Harrington, Ross W. ;
Clegg, William .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (16) :2705-2713
[6]   Design, synthesis and photophysical studies of dipyrromethene-based materials: insights into their applications in organic photovoltaic devices [J].
Bessette, Andre ;
Hanan, Garry S. .
CHEMICAL SOCIETY REVIEWS, 2014, 43 (10) :3342-3405
[7]   Porphyrins and BODIPY as Building Blocks for Efficient Donor Materials in Bulk Heterojunction Solar Cells [J].
Bucher, Leo ;
Desbois, Nicolas ;
Harvey, Pierre D. ;
Sharma, Ganesh D. ;
Gros, Claude P. .
SOLAR RRL, 2017, 1 (12)
[8]   High-Performance Solution-Processed Solar Cells and Ambipolar Behavior in Organic Field-Effect Transistors with Thienyl-BODIPY Scaffoldings [J].
Bura, Thomas ;
Leclerc, Nicolas ;
Fall, Sadiara ;
Leveque, Patrick ;
Heiser, Thomas ;
Retailleau, Pascal ;
Rihn, Sandra ;
Mirloup, Antoine ;
Ziessel, Raymond .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (42) :17404-17407
[9]   One-Pot Synthesis of Contracted and Expanded Porphyrins with meso-CF3 Groups [J].
Chen, Qiu-Cheng ;
Soll, Matan ;
Mizrahi, Amir ;
Saltsman, Irena ;
Fridman, Natalia ;
Saphier, Magal ;
Gross, Zeev .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (04) :1006-1010
[10]   High Performance Photovoltaic Applications Using Solution-Processed Small Molecules [J].
Chen, Yongsheng ;
Wan, Xiangjian ;
Long, Guankui .
ACCOUNTS OF CHEMICAL RESEARCH, 2013, 46 (11) :2645-2655