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BODIPY Compounds as Non-Innocent π -Spacers for DSSC Dyes

BODIPY Compounds as Non-Innocent π -Spacers for DSSC Dyes. Devin D. Machin , Catherine Bonnier, Bryan D. Koivisto *. Science at the Interface August 14, 2012 Department of Chemistry and Biology Ryerson University. The Opportunities For Solar Technology.

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BODIPY Compounds as Non-Innocent π -Spacers for DSSC Dyes

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  1. BODIPY Compounds as Non-Innocentπ-Spacers for DSSC Dyes Devin D. Machin, Catherine Bonnier, Bryan D. Koivisto* Science at the Interface August 14, 2012 Department of Chemistry and Biology Ryerson University

  2. The Opportunities For Solar Technology • Crystalline silicon photovoltaics (PV’s) dominate the solar technology market • They are a mature technology, efficient and robust • However, they are expensive and have limited design potential. Solar energy has promising potential

  3. The Dye Sensitized Solar Cell (DSSC) • The DSSC is a promising next generation PV technology • 1. A photon is absorbed • 2. The excited e- is injected into TiO2 • 3. The e- enters the circuit • 4. The dye molecule is reduced by the electrolyte

  4. The Dye Molecule • The dye molecule is the powerhouse of the DSSC • Sun, L. et al., J. Org. Chem., 2007, 9550. • Organic dyes typically follow a Donor-π-spacer-Acceptor motif • The use of BODIPY and a non-innocent π-spacer for DSSC dyes is explored

  5. Boron-Dipyrromethene(BODIPY) • A robust moiety, that is redox stable and therefore can be used to increase the absorption envelope and long-term stability of DSSC dyes. Conjugation is interrupted by the orientation of the Indicated phenyl group • Mau, M. et al., Dyes Pigments., 2012, 231. Indicated group is a poor electron donor Erten-Ela, S. et al., Org. Lett., 2008, 3300.

  6. Target molecules • A family of BODIPY dyes with modified conjugation lengths for red-shifted absorption

  7. Synthesis of Target 2a & 2b • Fluorescence of BODIPY is quenched through the addition of donor and anchor groups • 2b in DCM

  8. Synthesis of Target 5a & 5b • 5bin DCM

  9. Cyclic Voltammetryand DFT HOMO LUMO Calibrated vsFerrocene (not shown) B3LYP/6-31G

  10. UV-vis Spectra Comparison • Dyes 2b and 5b show red shifted absorptions tailing off to 630 nm • Hagfelt, A. et al., Chem Rev., 2010, 6595.

  11. Summary and Future work • 6 of 8 target molecules were successfully synthesized. • These dye molecules have promising physical properties (UV-vis, CV) • Dyes will be used in prototype devices to determine conversion efficiency • Future synthesis utilizing other organic frameworks as non-innocent π-spacers

  12. 12 Acknowledgements People Current Group Dr. Bryan Koivisto (PI) Dr. Catherine Bonnier (PDF) Devin Machin (BSc) Omar Abdi (BSc) Muhammad Yousaf (MSc) Left to Right: Devin, Catherine, Bryan, Muhammad, & Omar Funding

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