Optimization of distyryl-Bodipy chromophores for efficient panchromatic sensitization in dye sensitized solar cells

Versatility of Bodipy (4,4-difluoro-4-bora-3a,4a-diaza-s-indacene) dyes was further expanded in recent dye-sensitized solar cell applications. Here we report a series of derivatives designed to address earlier problems in Bodipy sensitized solar cells. In the best case example, an overall efficiency of a modest 2.46% was achieved, but panchromatic nature of the dyes is quite impressive. This is the best reported efficiency in liquid electrolyte solar cells with Bodipy dyes as photosensitizers.

[1]  Mohammad Khaja Nazeeruddin.  Michael Graetzel Festschrift, a tribute for his 60th Birthday , 2004 .

[2]  Siddik Icli,et al.  A panchromatic boradiazaindacene (BODIPY) sensitizer for dye-sensitized solar cells. , 2008, Organic letters.

[3]  A. Jäger-Waldau,et al.  Photovoltaics and renewable energies in Europe , 2007 .

[4]  Neil Robertson,et al.  Catching the rainbow: light harvesting in dye-sensitized solar cells. , 2008, Angewandte Chemie.

[5]  Tomas Edvinsson,et al.  A novel organic chromophore for dye-sensitized nanostructured solar cells. , 2006, Chemical communications.

[6]  Jianjun He,et al.  Modified phthalocyanines for efficient near-IR sensitization of nanostructured TiO(2) electrode. , 2002, Journal of the American Chemical Society.

[7]  Shiguo Sun,et al.  A Hg2+ fluorescent chemosensor without interference from anions and Hg2+-imaging in living cells , 2009 .

[8]  Biwu Ma,et al.  Bodipy-backboned polymers as electron donor in bulk heterojunction solar cells. , 2010, Chemical communications.

[9]  R. Thummel,et al.  Color tuning in new metal-free organic sensitizers (Bodipys) for dye-sensitized solar cells. , 2009, Chemistry.

[10]  Alexandre Haefelé,et al.  Boron asymmetry in a BODIPY derivative. , 2010, Organic letters.

[11]  E. Akkaya,et al.  Non-covalent functionalized SWNTs as delivery agents for novel Bodipy-based potential PDT sensitizers. , 2009, Chemical communications.

[12]  A. Ajayaghosh,et al.  Organogels as scaffolds for excitation energy transfer and light harvesting. , 2008, Chemical Society reviews.

[13]  Ruslan Guliyev,et al.  Selective manipulation of ICT and PET Processes in styryl-Bodipy derivatives: applications in molecular logic and fluorescence sensing of metal ions. , 2010, Journal of the American Chemical Society.

[14]  W. Dehaen,et al.  Palladium‐Catalyzed Coupling Reactions for the Functionalization of BODIPY Dyes with Fluorescence Spanning the Visible Spectrum , 2006 .

[15]  D. Citterio,et al.  Bright, color-tunable fluorescent dyes in the visible-near-infrared region. , 2008, Journal of the American Chemical Society.

[16]  Sung-Jin Kim,et al.  New BODIPY derivatives as OFF-ON fluorescent chemosensor and fluorescent chemodosimeter for Cu2+: cooperative selectivity enhancement toward Cu2+. , 2006, The Journal of organic chemistry.

[17]  R. Ziessel,et al.  Efficient synthesis of panchromatic dyes for energy concentration. , 2010, Angewandte Chemie.

[18]  Seigo Ito,et al.  Large pi-aromatic molecules as potential sensitizers for highly efficient dye-sensitized solar cells. , 2009, Accounts of chemical research.

[19]  J. Roncali,et al.  Multi-donor molecular bulk heterojunction solar cells: improving conversion efficiency by synergistic dye combinations , 2009 .

[20]  S. Haque,et al.  Towards optimisation of electron transfer processes in dye sensitised solar cells , 2004 .

[21]  Hidetoshi Miura,et al.  High-conversion-efficiency organic dye-sensitized solar cells with a novel indoline dye. , 2008, Chemical communications.

[22]  J. Roncali,et al.  BODIPY derivatives as donor materials for bulk heterojunction solar cells. , 2009, Chemical communications.

[23]  Onur Buyukcakir,et al.  Cyanide sensing via metal ion removal from a fluorogenic BODIPY complex , 2009 .

[24]  Eiji Suzuki,et al.  Alkyl-functionalized organic dyes for efficient molecular photovoltaics. , 2006, Journal of the American Chemical Society.

[25]  J. Roncali,et al.  A tailored hybrid BODIPY-oligothiophene donor for molecular bulk heterojunction solar cells with improved performances. , 2010, Chemical communications.

[26]  Kevin Burgess,et al.  BODIPY dyes and their derivatives: syntheses and spectroscopic properties. , 2007, Chemical reviews.

[27]  E. Akkaya,et al.  Synthesis of symmetrical multichromophoric Bodipy dyes and their facile transformation into energy transfer cassettes. , 2010, Chemistry.

[28]  J. Hupp,et al.  Dye sensitized solar cells: TiO2 sensitization with a bodipy-porphyrin antenna system. , 2010, Langmuir : the ACS journal of surfaces and colloids.

[29]  A. Ajayaghosh,et al.  Squaraine dyes: a mine of molecular materials , 2008 .

[30]  A. Harriman,et al.  The chemistry of Bodipy: A new El Dorado for fluorescence tools , 2007 .

[31]  K. Burgess,et al.  Syntheses and spectral properties of functionalized, water-soluble BODIPY derivatives. , 2008, The Journal of organic chemistry.

[32]  Molecular Designs and Syntheses of Organic Dyes for Dye-Sensitized Solar Cells , 2009 .

[33]  E. Akkaya,et al.  Thinking outside the silicon box: molecular and logic as an additional layer of selectivity in singlet oxygen generation for photodynamic therapy. , 2009, Journal of the American Chemical Society.

[34]  M. Grätzel,et al.  A low-cost, high-efficiency solar cell based on dye-sensitized colloidal TiO2 films , 1991, Nature.

[35]  E. Akkaya,et al.  Tetrastyryl-Bodipy dyes: convenient synthesis and characterization of elusive near IR fluorophores. , 2009, Organic letters.

[36]  E. Akkaya,et al.  Distyryl-boradiazaindacenes: facile synthesis of novel near IR emitting fluorophores , 2006 .

[37]  M. Fischer,et al.  Metal-free organic dyes for dye-sensitized solar cells: from structure: property relationships to design rules. , 2009, Angewandte Chemie.

[38]  Jani Kallioinen,et al.  Photoinduced ultrafast dye-to-semiconductor electron injection from nonthermalized and thermalized donor states. , 2002, Journal of the American Chemical Society.

[39]  Johannes C. Brendel,et al.  Solid-state dye-sensitized solar cells using red and near-IR absorbing Bodipy sensitizers. , 2010, Organic letters.

[40]  Juyoung Yoon,et al.  New BODIPY–triazine based tripod fluorescent systems , 2008 .

[41]  Mohammad Khaja Nazeeruddin,et al.  Conversion of light to electricity by cis-X2bis(2,2'-bipyridyl-4,4'-dicarboxylate)ruthenium(II) charge-transfer sensitizers (X = Cl-, Br-, I-, CN-, and SCN-) on nanocrystalline titanium dioxide electrodes , 1993 .

[42]  K. Rurack,et al.  Molecular Switching in the Near Infrared (NIR) with a Functionalized Boron-Dipyrromethene Dye. , 2001, Angewandte Chemie.

[43]  M. Grätzel.  Photoelectrochemical cells : Materials for clean energy , 2001 .

[44]  K. Ohkubo,et al.  Charge separation in a nonfluorescent donor-acceptor dyad derived from boron dipyrromethene dye, leading to photocurrent generation. , 2005, The journal of physical chemistry. B.

[45]  E. Akkaya,et al.  Solid-state emissive BODIPY dyes with bulky substituents as spacers. , 2009, Organic letters.

[46]  Y. Urano,et al.  Highly efficient and photostable photosensitizer based on BODIPY chromophore. , 2005, Journal of the American Chemical Society.

[47]  Shiguo Sun,et al.  Carboxyl BODIPY dyes from bicarboxylic anhydrides: one-pot preparation, spectral properties, photostability, and biolabeling. , 2009, The Journal of organic chemistry.

[48]  Anthony Harriman,et al.  The chemistry of fluorescent bodipy dyes: versatility unsurpassed. , 2008, Angewandte Chemie.