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
收藏
页数:11
相关论文
共 39 条
[21]   Novel D-A-D type dyes based on BODIPY platform for solution processed organic solar cells [J].
Liao, Junxu ;
Zhao, Hongbin ;
Xu, Yongjun ;
Cai, Zhuodi ;
Peng, Zaixi ;
Zhang, Wentao ;
Zhou, Weinan ;
Li, Bohong ;
Zong, Qiao ;
Yang, Xiaoxi .
DYES AND PIGMENTS, 2016, 128 :131-140
[22]   BODIPY dyes and their derivatives: Syntheses and spectroscopic properties [J].
Loudet, Aurore ;
Burgess, Kevin .
CHEMICAL REVIEWS, 2007, 107 (11) :4891-4932
[23]   Photoinduced intramolecular charge transfer in a series of differently twisted donor - Acceptor biphenyls as revealed by fluorescence [J].
Maus, M ;
Rettig, W ;
Bonafoux, D ;
Lapouyade, R .
JOURNAL OF PHYSICAL CHEMISTRY A, 1999, 103 (18) :3388-3401
[24]   Space-charge limited photocurrent [J].
Mihailetchi, VD ;
Wildeman, J ;
Blom, PWM .
PHYSICAL REVIEW LETTERS, 2005, 94 (12)
[25]   Carbazole-BODIPY conjugates: design, synthesis, structure and properties [J].
Misra, Rajneesh ;
Jadhav, Thaksen ;
Dhokale, Bhausaheb ;
Gautam, Prabhat ;
Sharma, Rekha ;
Maragani, Ramesh ;
Mobin, Shaikh M. .
DALTON TRANSACTIONS, 2014, 43 (34) :13076-13086
[26]   On the effect of formaldehyde and methylene-chloride on pyrroles. [J].
Pictet, A ;
Rilliet, A .
BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1907, 40 :1166-1172
[27]   Small molecule BODIPY dyes as non-fullerene acceptors in bulk heterojunction organic photovoltaics [J].
Poe, Ambata M. ;
Della Pelle, Andrea M. ;
Subrahmanyam, Ayyagari V. ;
White, William ;
Wantz, Guillaume ;
Thayumanavan, S. .
CHEMICAL COMMUNICATIONS, 2014, 50 (22) :2913-2915
[28]   Achieving the highest efficiency using a BODIPY core decorated with dithiafulvalene wings for small molecule based solution-processed organic solar cells [J].
Rao, R. Srinivasa ;
Bagui, Anirban ;
Rao, G. Hanumantha ;
Gupta, Vinay ;
Singh, Surya Prakash .
CHEMICAL COMMUNICATIONS, 2017, 53 (51) :6953-6956
[29]   BODIPY derivatives as donor materials for bulk heterojunction solar cells [J].
Rousseau, Theodulf ;
Cravino, Antonio ;
Bura, Thomas ;
Ulrich, Gilles ;
Ziessel, Raymond ;
Roncali, Jean .
CHEMICAL COMMUNICATIONS, 2009, (13) :1673-1675
[30]   The use of fluorescent Nile red and BODIPY for lipid measurement in microalgae [J].
Rumin, Judith ;
Bonnefond, Hubert ;
Saint-Jean, Bruno ;
Rouxel, Catherine ;
Sciandra, Antoine ;
Bernard, Olivier ;
Cadoret, Jean-Paul ;
Bougaran, Gael .
BIOTECHNOLOGY FOR BIOFUELS, 2015, 8