NonInnocent 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 ID: 271959
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Slide1
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 UniversitySlide2
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.
2
Solar energy has
promising potentialSlide3
The Dye Sensitized Solar
Cell (DSSC)3
The DSSC is a promising next generation PV technology
1.
A photon is absorbed
2.
The excited e
-
is injected into TiO
2
3.
The e
-
enters the circuit
4.
The dye molecule is reduced by the electrolyteSlide4
The Dye Molecule4
The dye molecule is the powerhouse of the DSSC
The use of BODIPY and a
non-innocent
π
-spacer for DSSC dyes is explored
Organic dyes typically follow a
Donor-
π
-spacer
-Acceptor
motif
Sun, L.
et al
.,
J. Org. Chem.,
2007
, 9550. Slide5
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.
5
Erten-Ela
, S.
et al
.,
Org.
L
ett
.,
2008
, 3300.
Mau, M.
et al
.,
D
yes Pigments.,
2012
, 231.
Conjugation is
i
nterrupted by the orientation of theIndicated phenyl groupIndicated group is a poor
electron donorSlide6
Target moleculesA family of BODIPY dyes with modified conjugation lengths for red-shifted absorption
6Slide7
Synthesis of Target 2a & 2b
7
2
b
in DCM
Fluorescence of BODIPY is quenched through the addition of donor and anchor groups Slide8
Synthesis of Target
5a & 5b
8
5b
i
n DCMSlide9
Cyclic Voltammetry
and DFT
9
HOMO
LUMO
B3LYP/6-31G
Calibrated
vs
Ferrocene
(not shown)Slide10
UV-
vis Spectra Comparison10
Hagfelt
, A.
et al
.,
Chem
Rev.,
2010
, 6595.
Dyes
2b
and
5b
show red shifted absorptions tailing off to 630 nmSlide11
Summary and Future work 6 of 8 target molecules were successfully synthesized.These dye molecules have promising physical properties (UV-
vis, CV)11
Dyes will be used in prototype devices to determine conversion efficiency
Future synthesis utilizing other organic frameworks as
non-innocent
π
-spacersSlide12
AcknowledgementsCurrent GroupDr. Bryan Koivisto (PI)
Dr. Catherine Bonnier (PDF)Devin Machin (BSc)Omar Abdi (BSc)Muhammad Yousaf (MSc)
Left to Right:
Devin, Catherine, Bryan,
Muhammad, & Omar
People
Funding
12