Quantum efficiency of 3, 5 dimethyl pyridine 2-

IJRET: International Journal of Research in Engineering and Technology eISSN: 2319-1163 | pISSN: 2321-7308
_______________________________________________________________________________________
Volume: 03 Issue: 01 | Jan-2014, Available @ http://www.ijret.org 250
QUANTUM EFFICIENCY OF 3, 5-DIMETHYL PYRIDINE 2-
CARBONITIRLE FOR DYE SENSITIZED SOLAR CELL AND
VIBRATIONAL SPECTRAL ANALYSIS OF THE DYE MOLECULE
Uthayakumar.B1
, G.Meenakshi2
, S.Ramadasse3
1
Research Scholar, 2,3
Associate Professor, Department of Physics, Kanchi Mamunivar Centre for Post Graduate
Studies, Lawspet, Puducherry, India
Abstract
Dye-sensitized solar cells (DSSC) attain consideration because of their sky-scraping light to electricity conversion efficiencies,
simple and low cost manufacturing. Fruitful efficiency of a DSSC is that it should convert photon into current even at wavelength
of UV. Present work aimed at quantum efficiency ( Light Harvesting Efficiency) of 3,5-dimethyl pyridine 2-carbonitirle. Density
functional theory (DFT) has been used to determine the ground state geometries of dye 3,5-dimethyl pyridine 2-carbonitirle. The
time dependant density functional theory (TDDFT) has been used to calculate the excitation energies. All the calculations were
performed in both gas and solvent phase. The improved light harvesting efficiency (LHE) and free energy change of electron
injection of newly designed sensitizers revealed that these materials would be an excellent sensitizers. It may also be due to
dendrites of methyl group and cyno group which is present in the study material. The experimental spectrum of FTIR and FT-
Raman supports the absorption levels.
Key Words: 3,5-dimethyl pyridine 2-carbonitirle,Dye-sensitized solar cells, Light harvesting efficiency, Density
functional Theory, FTIR, FT-Raman spectroscopy
-------------------------------------------------------------------***-----------------------------------------------------------------------
1. INTRODUCTION
Dye-sensitized solar cells (DSSC) attain consideration
because of their sky-scraping light to electricity conversion
efficiencies, simple and low cost manufacturing.1-3
The
sensitizer is a critical element in DSSC, which improves the
power conversion efficiency and increases the stability of the
devices. The Ruthenium base photosensitizers give a solar
energy to electricity conversion efficiency of 10% in
average.2
Metal free organic DSSCs have benefits over metal
holding sensitizers, e.g., easy and cheap preparation methods,
environment friendly and elevated molar extinction
coefficient.4
Different metal free dyes have been examined
which have comparable efficiencies to metal holding
sensitizers.5-7
Designing of dye sensitizer plays an important
role in the optimization of DSSC,8
and it depends on the
quantitative information of dye sensitizer. In most of the
organic sensitizers presence of donor, bridge and acceptor
(DBA) moieties is very important to get better performance
of the photo induced intramolecular charge transfer.
Figure 1(a). Schematic illustration of the dye-sensitized TiO2
interface
Figure.1(b): Schematic pictures of (A) the basic parts, and
(B) the photoinduced processes of a dye-sensitized solar cell

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During electronic transition, charge transfer depends on the
conjugation across the donor and anchoring groups.
Efficiency of organic sensitizers decreases due to dye
aggregation and charge recombination.9
To model and design
efficient metal-free sensitizers for DSSC, suitable DBA
systems are needed whose properties can be altered by
applying the drivable structural modifications. In this
research work, we report an organic dye 3,5-dimethyl
pyridine 2-carbonitrile, shows the light harvesting efficiency
which is overall of 12% . We also investigated its Molecular
structure, vibrational spectroscopic FT-IR,FT-Raman
analysis.
2. EXPERIMENTAL
Freshly prepared 3,5-dimethyl pyridine 2-carbonitrile has
been purchased from Sigma Aldrich and used without further
purification. Fourier transform infrared spectra of the title
compound is measured at the room temperature in the region
4000-400 cm-1
using a BRUCKER IFS-66 V FTIR
spectrometer at a resolution of ± 1cm-1
equipped with a MCT
detector, a KBr beam splitter and globar source. The FT-
Raman spectrum of 3,5-dimethyl pyridine 2-carbonitrile is
recorded on a BRUKER IFS -66 V model interferometer
equipped with FRA-106 FT-Raman accessory in the 3500–
100 cm−1
Stokes region using the 1064 nm line of a Nd: YAG
laser for excitation operating at 200 mW power. The reported
wave numbers are believed to be accurate within ±1 cm−1
.
Figure.2: Chemical Structure of 3,5-dimethyl pyridine 2-
carbonitrile
3. COMPUTATIONAL DETAILS
Density functional theory (DFT) and time dependant density
functional theory (TD-DFT) calculations were performed to
determine geometries, electronic structures and electronic
absorption spectra selected dye. All the calculations, both in
gas and solvent phase, were performed using Gaussian09
package.12
All calculations were performed by employing
CAM-B3LYP functional and 6-311+G* basis set. The free
energy change for electron injection onto a titanium dioxide
(TiO2) surface and dye’s excited state oxidation potential
were calculated using mathematical equations.
The light harvesting efficiency (LHE) was determined by
formula14
:
LHE = 1−10–f
Where f is the oscillator strength of dye
4. RESULTS AND DISCUSSION
4.1. The geometric structure:
The optimized geometry of the 3,5-dimethylpyridine 2-
carbonitrile is shown in Figure.3, and the bond lengths, bond
angles and dihedral angles are listed in Table.1(a),(b),(c).
Since the crystal structure of the exact title compound is not
available till now, the optimized structure can be only be
compared with other similar systems for which the crystal
structures have been solved. From the theoretical values we
can find that most of the optimized bond lengths, bond angles
and dihedral angles. The optimized bond lengths of C-C
single and double bond inside and outside the pyridine ring
differs. These values are reported in Table 1(a),(b),(c). The
bonds length between Carbon atoms C1-C2=1.4087Å, C3-C4
=1.3961 Å and C2-C3=1.3935 Å, C4-C5 =1.3998 Å these C-
C bonds are skeletal C-C bonds of the pyridine ring which
are having merely same value of bond length this is due to
interaction made by localized electron inside the ring. Bond
angle betweenC1-N6-C5 is 117.768 which support the
presence of Nitrogen in pyridine ring. Dihedral angle implies
the sample under study have a ring structure.
Figure.3: Optimized geometrical structure of dye 3,5-
dimethylpyridine 2-carbonitrile.
Table 1(a): Bond lengths (Å) of the dye 3,5-
dimethylpyridine 2-carbonitrile
Bond length B3LYP/6-311++G(d,p)(Å)
C1-C2 1.4087
C1-N6 1.3384
C1-C9 1.4405
C2-C3 1.3935
C2-C8 1.5055
C3-C4 1.3961
C3-H11 1.0861
C4-C5 1.3998
C4-C7 1.5056
C5-N6 1.3299
C5-H12 1.0868
C7-H13 1.0914

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C7-H14 1.094
C7-H15 1.094
C8-H16 1.0936
C8-H17 1.0936
C8-H18 1.091
C9-N10 1.1549
Table 1(b): Bond angle (°) of the dye 3,5-dimethylpyridine
2-carbonitrile
Bond angle B3LYP/6-311++G(d,p) (°)
C2-C1-N6 124.1532
C2-C1-C9 119.4946
N6-C1-C9 116.3521
C1-C2-C3 116.1263
C1-C2-C8 121.822
C3-C2-C8 122.0517
C2-C3-C4 121.1168
C2-C3-H11 119.1001
C4-C3-H11 119.783
C3-C4-C5 116.8421
C3-C4-C7 121.7516
C5-C4-C7 121.4063
C4-C5-N6 123.9938
C4-C5-H12 120.1051
N6-C5-H12 115.9011
C1-N6-C5 117.7678
C4-C7-H13 111.2781
C4-C7-H14 111.0938
C4-C7-H15 111.0924
H13-C7-H14 107.9317
H13-C7-H15 107.9312
H14-C7-H15 107.3447
C2-C8-H16 111.2016
C2-C8-H17 111.2009
C2-C8-H18 110.8354
H16-C8-H17 106.8458
H16-C8-H18 108.3013
H17-C8-H18 108.3014
Table 1(c): Dihedral angle (°) of the dye 3,5-
dimethylpyridine 2-carbonitrile
Dihedral angle B3LYP/6-311++G(d,p) (°)
N6-C1-C2-C3 0.001
N6-C1-C2-C8 180.0002
C9-C1-C2-C3 -179.9972
C9-C1-C2-C8 0.002
C2-C1-N6-C5 -0.0013
C9-C1-N6-C5 179.997
C1-C2-C3-C4 0.0001
C1-C2-C3-H11 -179.9997
C8-C2-C3-C4 -179.9992
C8-C2-C3-H11 0.001
C1-C2-C8-H16 59.4652
C1-C2-C8-H17 -59.4652
C1-C2-C8-H18 179.9961
C3-C2-C8-H16 -120.5356
C3-C2-C8-H17 120.526
C3-C2-C8-H18 -0.0047
C2-C3-C4-C5 -0.0007
C2-C3-C4-C7 -180.0027
H11-C3-C4-C5 -180.0009
H11-C3-C4-C7 -0.0029
C3-C4-C5-N6 0.0004
C3-C4-C5-H12 180.0012
C7-C4-C5-N6 180.0012
C7-C4-C5-H12 0.0032
C3-C4-C7-H13 -180.0068
C3-C4-C7-H14 59.7042
C3-C4-C7-H15 -59.7194
C5-C4-C7-H13 -0.009
C5-C4-C7-H14 -120.2979
C5-C4-C7-H15 120.2785
C4-C5-N6-H11 0.0006
H12-C5-N6-C1 -180.003
4.2. Vibrational spectral Analysis
Figure 5 and 6 shows the observed IR and Raman spectra of
3,5-dimethylpyridine 2-carbonitrile respectively. The 3,5-
dimethylpyridine 2-carbonitrile molecule give rise to three
C-H stretching, two C-H torsion vibrations, two C-H out of
plane bending vibrations ,one C-H in-plane bending
vibration, four wagging C-C-N vibrations, one C-C-N
bending vibration, two C=C stretching vibrations, three C-N
stretching vibrations, one C-C-C torsion vibration, one C-C-
C in plane vibration, one ring stretching and one ring
deformation were assigned using experimental spectrum.
The strongest IR absorption for 3,5-dimethylpyridine 2-
carbonitrile corresponds to the vibrational mode 28 near
about 1455 cm-1
, which is corresponding to stretching mode
of C=C bonds. The next stronger IR absorption is attributed
to vibrational mode 16 near about 895 cm-1
, corresponding to
the Torsion mode of C-H bonds. In the Raman spectrum,
however, the strongest activity mode is the vibrational mode
29 near about 2213 cm-1
, which is corresponding to
stretching mode of C-N triple bond. This peak is also
observed in FTIR spectrum at 2224 cm-1
.

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4.3. C–H vibrations
The C–H stretching vibrations in the benzene derivatives
arises from non-degenerate mode (3072 cm−1
) and two
degenerate modes (3047 cm−1
), (3099 cm−1
). In this region,
the bands are not appreciably affected by the nature of
substituents. Hence in the present investigation, the FT-IR
bands at 3057, 3022 cm−1
and FT-Raman bands at 3059,
3009 cm−1
have been assigned to C–H stretching vibrations.
In general most of them are weak in either the FT-Raman or
FT-IR, with the exception of 3059 cm−1
which appears as
very strong band in the FT-Raman spectra is assigned C–H
in-phase stretching mode. The upper limit of frequency
comparatively decreases may be due to the presence of
methyl group. The C–H in-plane bending vibrations appear in
the region 1000–1520 cm−1
and C–H out of- plane bending
vibrations in the range of 700–1000 cm−1
. The bands
corresponding to the C–H in-plane bending modes of
pyridine are observed at 1177 and 1081 cm−1
in the FT-IR
spectra. The corresponding calculated modes are dominated
by C-H in plane bending, and coupled mostly with CC
stretching. The medium strong bands observed at 947, 898
and 866, 812 cm−1
in the FT-IR spectrum modes of pyridine.
Figure.4: Observed FT-IR Spectra of 3,5-dimethylpyridine 2-carbonitrile
Figure.5: Observed FT-Raman Spectra of 3,5-dimethylpyridine 2-carbonitrile
433.48
473.97
517.43
572.71
613.58
723.53747.76
838.81
895.55
964.02
1045.10
1131.42
1213.90
1265.13
1375.95
1454.74
1562.92
1595.54
1650.52
1833.87
1886.31
2224.46
2526.36
2928.07
2990.50
3646.23
3708.57
3850.81
1
2
3
4
5
6
7
8
9
10
11
%T
5001000150020002500300035004000
Wavenumbers (cm-1)
0
20000
40000
60000
80000
100000
120000
140000
160000
180000
200000
0 1000 2000 3000 4000 5000
Wavelength (nm)
I
N
T
E
N
S
I
T
Y

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4.4. C–C vibrations
The C–C stretching frequencies are generally predicted in
the region 650–1650 cm−1
. In pyridine, the C–C stretching
frequencies arise from the two doubly degenerated
vibrations (1596 cm−1
) and (1485 cm−1
) and two non-
degenerate modes at (1300 cm−1
) and (998 cm−1
) which
corresponds to skeletal vibrations. The doubly degenerated
(1485 cm−1
) mode is basically a ring deformation, since it
involves both stretching and bending of the C–C bonds. The
frequency of the vibrational pair in substituted pyridine is
rather insensitive of substitution. The strong bands observed
at 1318, 1305 cm−1
in FT-IR spectrum are assigned to 40%
contribution of the CC-stretching mode. The CC in-plane
bending modes result from non-degenerate value (1010
cm−1
).
4.5. Methyl group vibrations
The asymmetric and symmetric stretching modes of methyl
group attached to the pyridine ring are usually downshifted
due to electronic effects and are expected in the range
2850–3000 cm−1
for asymmetric and symmetric stretching
vibrations. From spectrum the asymmetric stretching CH3
mode in which two C–H bonds of the methyl group are
extending while the third one is contracting. The second
arises from symmetrical stretching CH3 in which all three of
the C–H bonds extend and contract in phase. The two CH3
frequencies are calculated to be 2933 and 2931 cm−1
, which
are well comparable with the experimental values observed
at 2913(m) cm−1
, 2862(m) cm−1
in FT-IR and 2915 (m)
cm−1
, 2862 (m) cm−1
in FT-Raman spectra. The frequency of
calculated values of CH3 frequencies and 2979 cm−1
observed only in FT-IR spectra at 2933 (m) cm−1. The two
CH3 out of plane modes are calculated at 2830 and 2824
cm−1
both are not observed from experiment. In many
molecules the symmetric deformation labeled CH3
symmetric bending and CH3 in plane bending appears with
an intensity varying from medium to strong and expected in
the range 1380±25 cm−1
. The two CH3 stretching bending
frequencies are observed at 1379 and 1361 cm−1
. Out of
these two modes one is observed in the FT-IR and FT-
Raman spectra at 1377 and 1379 cm−1. The out-of-plane
rocking in the region 970±70 cm−1
is more difficult to find
among the C–H out-of-plane deformations.
4.6. Quantum Efficiency
Light harvesting efficiency of 3,5-dimethylpyridine 2-
carbonitrile is calculated from the oscillator value obtained
from TDDFT and tabulated in Table.3 , the highest light
harvesting efficiency value 0.8611 is obtained at 165.84nm
in solution and 0.7882 is obtained at 163.61nm in gas
phase. Each photon ejects one electron from a molecule of
the dye, hence 3,5-dimethyl pyridine 2-carbonitrile achieve
up to 86% of efficiency in solution and 78% in vacuum at
UV region. Average light harvesting efficiency is calculated
and the result is 12.7976% in solution and 12.2604% in gas
phase.
Table 2: Light Harvesting Efficiency of the Dye
Light Harvesting Efficiency
of the dye in SOLUTION
Light Harvesting Efficiency
of the dye in GAS PHASE
Wavelength(nm) ηηηη% Wavelength(nm) ηηηη%
218.58 0.4461 215.28 0.3390
207.74 0.0579 211.14 0.0133
205.25 0.01213 207.65 0.0779
174.11 0.00757 175.47 0.00597
170.05 0.01599 173.19 0.00046
168.86 0.7418 169.43 0.00391
166.11 0.00688 165.27 0.6251
165.84 0.8611 163.61 0.7882
158.72 0.00023 160.20 0.0084
157.13 0.00459 159.51 0.00023
154.92 0.1318 156.72 0.1696
153.94 0.0000 155.86 0.0000
150.94 0.0993 153.14 0.01213
150.92 0.1104 151.84 0.3583
145.53 0.00757 147.21 0.01916
141.88 0.00207 144.45 0.00069
141.21 0.00962 141.98 0.01122
140.09 0.00574 141.36 0.0000
138.96 0.0124 139.40 0.00253
137.61 0.02634 137.16 0.01599

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Table 3: Computed excitation energies, electronic transition
configurations and oscillator strengths(f) for the optical
transitions with f>.01 of the absorption bands in visible and
near-UV region for the dye 3,5-dimethyl pyridine2-
carbonitrile (in Gas phase)
State
Configuration
composition
(corresponding
transition orbital)
Excitation
energy
(eV/nm)
Oscillator
Strength
(f)
1
0.15377 (34 -> 41)
-0.26138 (34 -> 45)
-0.26132 (35 -> 39)
0.58476 (35 -> 42)
5.7593/215
.28
.1798
2
-0.20848 (33 -> 39)
-0.19004 (33 -> 41)
0.52608 (33 -> 42)
0.10413 (33 -> 45)
0.16362 (33 -> 51)
-0.11259 (33 -> 92)
5.8722/211
.14
.0058
3
-0.18561 (34 -> 39)
0.37295 (34 -> 42)
-0.31910 (35 -> 41)
0.45852 (35 -> 45)
0.13445 (35 -> 51)
5.9707/207
.65
.0352
4
0.53817 (35 -> 36)
0.24513 (35 -> 38)
-0.26883 (35 -> 44)
-0.10565 (35 -> 47)
-0.10548 (35 -> 55)
7.0658/175
.47
.0026
5
-0.11226 (31 -> 59)
0.14730 (31 -> 64)
0.31770 (32 -> 42)
-0.17681 (32 -> 45)
-0.13911 (32 -> 65)
-0.16490 (32 -> 69)
0.14285 (33 -> 45)
7.1588/173
.19
.0002
6
-0.27487 (33 -> 41)
-0.23405 (33 -> 42)
0.50529 (33 -> 45)
0.11998 (33 -> 51)
7.3177/169
.43
.0017
7
-0.13317 (33 -> 39)
0.33403 (33 -> 41)
-0.19705 (33 -> 42)
0.46913 (33 -> 45)
0.10834 (33 -> 48)
-0.11956 (33 -> 54)
7.4642/166
.11
.0030
8
0.26666 (34 -> 41)
-0.25917 (34 -> 42)
0.44797 (34 -> 45)
0.12710 (34 -> 48)
-0.11695 (35 -> 41)
-0.10233 (35 -> 42)
7.4763/165
.84
.8572
9
-0.12656 (30 -> 41)
0.21151 (31 -> 56)
0.15802 (31 -> 58)
-0.10103 (31 -> 64)
-0.16199 (32 -> 39)
0.29416 (32 -> 41)
0.12989 (32 -> 45)
-0.14783 (32 -> 63)
0.12348 (32 -> 66)
-0.13215 (32 -> 69)
-0.10701 (32 -> 79)
-0.18415 (35 -> 56)
-0.10845 (35 -> 58)
7.8115/158
.72
.0001
10
0.30079 (34 -> 36)
-0.12860 (34 -> 44)
0.53274 (35 -> 37)
0.11252 (35 -> 49)
7.8905/157
.13
.0020
11
0.11613 (31 -> 39)
-0.18478 (31 -> 41)
0.14033 (32 -> 56)
0.10430 (32 -> 58)
0.42258 (35 -> 39)
0.20340 (35 -> 41)
0.15516 (35 -> 42)
0.19827 (35 -> 48)
-0.10974 (35 -> 51)
8.0032/154
.92
.0614
12
0.27588 (34 -> 36)
-0.11537 (34 -> 44)
-0.10059 (34 -> 47)
-0.17494 (35 -> 36)
-0.26501 (35 -> 37)
0.45345 (35 -> 38)
-0.11851 (35 -> 46)
0.11990 (35 -> 58)
8.0540/153
.94
.0000
13
-0.16475 (31 -> 41)
0.13264 (32 -> 56)
0.27169 (34 -> 36)
0.10159 (34 -> 40)
-0.13414 (34 -> 44)
0.12067 (35 -> 36)
-0.13680 (35 -> 37)
-0.21751 (35 -> 38)
-0.19224 (35 -> 39)
-0.18192 (35 -> 41)
0.14083 (35 -> 43)
8.2140/150
.94
.0454
14
0.16955 (31 -> 41)
-0.13702 (32 -> 56)
-0.10160 (32 -> 58)
0.26196 (34 -> 36)
-0.12746 (34 -> 44)
0.11674 (35 -> 36)
-0.13559 (35 -> 37)
-0.21034 (35 -> 38)
8.2154/150
.92
.0508
15
-0.30245 (35 -> 36)
-0.15788 (35 -> 37)
-0.15912 (35 -> 38)
-0.42962 (35 -> 44)
-0.25239 (35 -> 47)
0.10751 (35 -> 50)
-0.12375 (35 -> 53)
8.5194/145
.53
.0033

_______________________________________________________________________________________
-0.11797 (35 -> 55)
16
-0.18404 (34 -> 37)
-0.19197 (35 -> 38)
0.48689 (35 -> 40)
-0.33905 (35 -> 43)
0.10811 (35 -> 44)
-0.10276 (35 -> 65)
8.7386/141
.88
.0009
17
-0.17304 (34 -> 38)
0.10398 (35 -> 37)
0.15111 (35 -> 38)
0.40633 (35 -> 40)
0.41638 (35 -> 43)
8.7799/141
.21
.0042
18
-0.30212 (34 -> 39)
-0.20100 (34 -> 41)
-0.11772 (34 -> 42)
-0.20479 (35 -> 41)
0.37188 (35 -> 42)
0.31961 (35 -> 45)
8.8504/140
.09
.0025
19
-0.32104 (34 -> 37)
0.43895 (34 -> 38)
-0.13453 (34 -> 40)
-0.11421 (34 -> 44)
-0.17331 (34 -> 46)
-0.10973 (34 -> 53)
0.18038 (35 -> 43)
8.9225/138
.96
.0054
20
0.39563 (33 -> 36)
-0.19618 (33 -> 37)
0.34153 (33 -> 38)
0.15808 (33 -> 40)
-0.11647 (33 -> 43)
-0.15267 (33 -> 46)
-0.13717 (33 -> 47)
0.10273 (33 -> 55)
-0.10699 (33 -> 57)
9.0098/137
.61
.0116
Figure .4: Light Harvesting Efficiency of the dye in
SOLUTION
Figure .5: Light Harvesting Efficiency of the dye in GAS
PHASE
5. CONCLUSION
The electronic absorption spectral features in FTIR, FT-
Raman, visible and near-UV region qualitatively agrees with
TD-DFT calculations. The absorptions are all ascribed to
π→π* transition. Three excited states with the lowest
excited energies of 3,5-dimethylpyridine 2-carbonitrile is the
result of photo induced electron transfer that contributes
sensitization of photo-to current conversion. The interfacial
electron transfer between semiconductor TiO2 electrode and
dye sensitizer3,5-dimethylpyridine 2-carbonitrile is due to
electron injection from excited dye as donor to the
semiconductor conduction band. Based on the analysis of
geometries, quantum efficiency, and spectral properties of
3,5-dimethylpyridine 2-carbonitrile, the nitro group and
methyl group enlarges the distance between electron donor
group and semiconductor surface, and decreases the time
scale of the electron injection rate, which results in higher
conversion efficiency at maximum absorption. This
indicates that the choice of the appropriate conjugate bridge
in dye sensitizer is very important to improve the
performance of DSSC.
REFERENCES
[1]. Regan, B. O.; Gratzel, M. Nature 1991, 353, 737-740.
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Selloni, A.;Viscardi, G.; Liska, P.; Ito, S.; Takeru, B.;
Grätzel, M. J. Am. Chem. Soc. 2005, 127, 16835-16847.
0
0.2
0.4
0.6
0.8
140 160 180 200 220
Wavelength (nm)
η
%
0
0.2
0.4
0.6
0.8
140 160 180 200 220
Wavelength (nm)
η
%
Wavelength (nm)
η
%

_______________________________________________________________________________________
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Adv Mater 2009, 21, 4087-4108.
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