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DANIEL MORALES SALAZAR
04/10/2013
CHEM 4803/6171
Synthesis of Low Spin Iron Complex
as Potential Redox Mediator for Dye
Sensitized Solar Cells
Representation of a Dye Sensitized Solar Cell
-LUMO potential of the dye
must be more negative than
the potential of the TiO2
Conduction Band edge (-0.5
V).
-HOMO potential of the dye
must be more positive than
Redox potential of electrolyte
for efficient dye regeneration.
Important electron processes in a DSSC
Regeneration and Recombination kinetics
(2) 100 fs to 100 ps
(3) μs range
(5) μs to ms range
(6) ms to s
(7) ns
I−/I3
− Redox Couple

Open-circuit Voltage (Voc)
- Increasing the redox potential of the electrolyte
increases Voc and reduces overpotential losses.
Important Requirements for New
Electrolytes
 Positive redox potential to maximize/optimize Voc (1.2 V), yet allowing
enough driving force to regenerate photo-oxidized dye (0.18 V-0.4 V vs.
NHE).
 Slow recombination kinetics (5) and (6).
 Negligible light absorption in the visible region.
Alternative Redox Mediators
Co(II/III)(bpy)3, 0.535 V Co(II/III)(bpy-pz)2, 0.86 V Fc/Fc+, 0.62 V
• Fast recombination
kinetics, poor dye
regeneration
• Not optimal with Pt-
coated counter electrode
• Very fast
recombination kinetics
Proposed Research
 Hypothesis: Synthesis of low spin Fe(II/III) iron
complexes, with a fast self-exchange electron rate,
and a large redox potential, as alternative redox
mediators in DSSCs with a high Voc.
1. ([Fe(bphen)3]2+/3+)
2. ([Fe(phen)3]2+/3+)
R=Me, Ph, OR2
1. 2.
Motivations
 Potential reversibility between the Fe2+/3+ species and
possibility to tune the redox potential through ligand
modifications.
 Larger self-exchange electron rate than cobalt analogs due to
smaller reorganizational energy going from presumably low
spin d6 to low spin d5 electron configuration. Dye regeneration.
 Bulky electron donating groups can function as insulating
spacers, slowing down dark current.
k11= 1.0 x 106 M-1s-1 k11= 1.0 x 10-9 M-1s-1
Motivations
Generally, the observed trends in the redox potentials are dependent on
geometrical distortions caused by the introduced ligands.
Potential Drawbacks
 The redox potential of the parent complex
([Fe(phen)3]2+/3+) (1.22 V vs SHE) must be lowered
by 0.2 V to allow dye regeneration.
 Light absorption in the visible spectrum (400-700
nm) might reduce the photocurrent.
 Ligand substitutions at the 5,6 positions are barely
described in the literature.
 Faster self-exchange electron rates are also related
to faster recombination kinetics.
Synthesis of benzo[f][1,10]phenanthroline ligand
The syntheses of ligands as well as the ferrous complexes are
described in the literature. Low yields are reported for the ligands,
ranging from 15 to 30% due to multiple steps
Skraup
synthesis
Characterization of the complexes
 1H-NMR, 13C-NMR, ESR (Fe3+), IR spectroscopy,
and high resolution mass spectroscopy can be used
to characterize the ligands and complexes.
 Magnetic susceptibility measurements through the
Evans method can be used to corroborate the low
spin nature of the [Fe(bphen)3]2+/3+ complexes.
 UV/Vis/NIR absorption spectra are obtained.
 Cyclic voltammetry experiments are
performed to fulfill the reversibility criteria
Characterization of the complexes
 Single-crystal X-ray diffraction
 NMR line-broadening technique is used to measure
the electron transfer self-exchange rate. Faster self-
exchange translates into faster regeneration kinetics.
Preparation of electrolytes
 Typical example of an electrolyte preparation: “The
electrolyte consists of 0.22 M [Fe(bphen)3]2+ , 0.05 M
[Fe(bphen)3]3+ , 0.1 M LiClO4, and 0.2 M 4-tert-
butylpyridine in acetonitrile.”
Decreases
photocurrent,
increases
photovoltage
Increases
photocurrent
, decreases
photovoltage
Experiments with electrolytes
 The redox potential of the electrolytes is calculated using
the Nernst equation and the formal potentials obtained
from cyclic voltammetry.
 YD2-o-C8 porphyrin dye (1.29 V vs. NHE)
 J/V and IPCE spectra.
- Octyloxy groups reduce charge
recombination
- 2.12 x 105 M-1 cm-1 (400 to 500 nm)
References
 1. Ooyama, Y; Harima Y. ChemPhysChem. 2012, 13, 4032.
 2. A. Listorti, B. O’Regan and J. R. Durrant, Chem. Mater., 2011, 23, 3381-3399.
 3. Boschloo, G.; Hagfeldt, A. Acc. Chem. Res. 2009, 42, 1819−1826.
 4. Hardin, B; McGehee, M. Nat. Phot. 2012, 6, 162-169.
 5. Yum, J.; Gratzel, M; Baranoff, E. Nat. Comm. 2011, 3, 1-8.
 6. Mayer, J; Yoder, J. J. Am. Chem Soc. 2003, 125. 2629-2640.
 7. Slattery, S. Inorg. Chim. Act. 2004, 357, 202-206.
 8. Hamman, T; Xie, Y. J. Phys Chem. Lett. 2013, 4, 328-332.
 9. Koft, E; Case, F. J. Org. Chem., 1962, 27 , 865–868.
 10. Jameson, D; Anand, R. J. Chem. Educ., 2000, 77 , 88.
 11. Hara, K. and Arakawa, H. Handbook of Photovoltaic Science and Engineering, 2005, 15, John Wiley & Sons, Ltd,
Chichester, UK.
 12. Yella, A.; Lee, H.-W.; Tsao, H. N.; Yi, C.; Chandiran, A. K.; Nazeeruddin, M. K.; Diau, E. W.-G.; Yeh, C.-Y.;
Zakeeruddin, S. M.; Grätzel, M. Science 2011, 334,629−634.

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Synthesis of low spin iron complex as potential redox mediator for DSCs

  • 1. DANIEL MORALES SALAZAR 04/10/2013 CHEM 4803/6171 Synthesis of Low Spin Iron Complex as Potential Redox Mediator for Dye Sensitized Solar Cells
  • 2. Representation of a Dye Sensitized Solar Cell -LUMO potential of the dye must be more negative than the potential of the TiO2 Conduction Band edge (-0.5 V). -HOMO potential of the dye must be more positive than Redox potential of electrolyte for efficient dye regeneration.
  • 3. Important electron processes in a DSSC Regeneration and Recombination kinetics (2) 100 fs to 100 ps (3) μs range (5) μs to ms range (6) ms to s (7) ns
  • 5. Open-circuit Voltage (Voc) - Increasing the redox potential of the electrolyte increases Voc and reduces overpotential losses.
  • 6. Important Requirements for New Electrolytes  Positive redox potential to maximize/optimize Voc (1.2 V), yet allowing enough driving force to regenerate photo-oxidized dye (0.18 V-0.4 V vs. NHE).  Slow recombination kinetics (5) and (6).  Negligible light absorption in the visible region. Alternative Redox Mediators Co(II/III)(bpy)3, 0.535 V Co(II/III)(bpy-pz)2, 0.86 V Fc/Fc+, 0.62 V • Fast recombination kinetics, poor dye regeneration • Not optimal with Pt- coated counter electrode • Very fast recombination kinetics
  • 7. Proposed Research  Hypothesis: Synthesis of low spin Fe(II/III) iron complexes, with a fast self-exchange electron rate, and a large redox potential, as alternative redox mediators in DSSCs with a high Voc. 1. ([Fe(bphen)3]2+/3+) 2. ([Fe(phen)3]2+/3+) R=Me, Ph, OR2 1. 2.
  • 8. Motivations  Potential reversibility between the Fe2+/3+ species and possibility to tune the redox potential through ligand modifications.  Larger self-exchange electron rate than cobalt analogs due to smaller reorganizational energy going from presumably low spin d6 to low spin d5 electron configuration. Dye regeneration.  Bulky electron donating groups can function as insulating spacers, slowing down dark current. k11= 1.0 x 106 M-1s-1 k11= 1.0 x 10-9 M-1s-1
  • 9. Motivations Generally, the observed trends in the redox potentials are dependent on geometrical distortions caused by the introduced ligands.
  • 10. Potential Drawbacks  The redox potential of the parent complex ([Fe(phen)3]2+/3+) (1.22 V vs SHE) must be lowered by 0.2 V to allow dye regeneration.  Light absorption in the visible spectrum (400-700 nm) might reduce the photocurrent.  Ligand substitutions at the 5,6 positions are barely described in the literature.  Faster self-exchange electron rates are also related to faster recombination kinetics.
  • 11. Synthesis of benzo[f][1,10]phenanthroline ligand The syntheses of ligands as well as the ferrous complexes are described in the literature. Low yields are reported for the ligands, ranging from 15 to 30% due to multiple steps Skraup synthesis
  • 12. Characterization of the complexes  1H-NMR, 13C-NMR, ESR (Fe3+), IR spectroscopy, and high resolution mass spectroscopy can be used to characterize the ligands and complexes.  Magnetic susceptibility measurements through the Evans method can be used to corroborate the low spin nature of the [Fe(bphen)3]2+/3+ complexes.  UV/Vis/NIR absorption spectra are obtained.  Cyclic voltammetry experiments are performed to fulfill the reversibility criteria
  • 13. Characterization of the complexes  Single-crystal X-ray diffraction  NMR line-broadening technique is used to measure the electron transfer self-exchange rate. Faster self- exchange translates into faster regeneration kinetics.
  • 14. Preparation of electrolytes  Typical example of an electrolyte preparation: “The electrolyte consists of 0.22 M [Fe(bphen)3]2+ , 0.05 M [Fe(bphen)3]3+ , 0.1 M LiClO4, and 0.2 M 4-tert- butylpyridine in acetonitrile.” Decreases photocurrent, increases photovoltage Increases photocurrent , decreases photovoltage
  • 15. Experiments with electrolytes  The redox potential of the electrolytes is calculated using the Nernst equation and the formal potentials obtained from cyclic voltammetry.  YD2-o-C8 porphyrin dye (1.29 V vs. NHE)  J/V and IPCE spectra. - Octyloxy groups reduce charge recombination - 2.12 x 105 M-1 cm-1 (400 to 500 nm)
  • 16. References  1. Ooyama, Y; Harima Y. ChemPhysChem. 2012, 13, 4032.  2. A. Listorti, B. O’Regan and J. R. Durrant, Chem. Mater., 2011, 23, 3381-3399.  3. Boschloo, G.; Hagfeldt, A. Acc. Chem. Res. 2009, 42, 1819−1826.  4. Hardin, B; McGehee, M. Nat. Phot. 2012, 6, 162-169.  5. Yum, J.; Gratzel, M; Baranoff, E. Nat. Comm. 2011, 3, 1-8.  6. Mayer, J; Yoder, J. J. Am. Chem Soc. 2003, 125. 2629-2640.  7. Slattery, S. Inorg. Chim. Act. 2004, 357, 202-206.  8. Hamman, T; Xie, Y. J. Phys Chem. Lett. 2013, 4, 328-332.  9. Koft, E; Case, F. J. Org. Chem., 1962, 27 , 865–868.  10. Jameson, D; Anand, R. J. Chem. Educ., 2000, 77 , 88.  11. Hara, K. and Arakawa, H. Handbook of Photovoltaic Science and Engineering, 2005, 15, John Wiley & Sons, Ltd, Chichester, UK.  12. Yella, A.; Lee, H.-W.; Tsao, H. N.; Yi, C.; Chandiran, A. K.; Nazeeruddin, M. K.; Diau, E. W.-G.; Yeh, C.-Y.; Zakeeruddin, S. M.; Grätzel, M. Science 2011, 334,629−634.