Synthesis of novel tetra (4-tritylphenoxy) substituted metallophthalocyanines and investigation of their aggregation, photovoltaic, solar cell properties

Article abstract of DOI:10.1080/24701556.2019.1572624

4-(4-tritylphenoxy) phthalonitrile was synthesized and characterized. Copper, zinc and cobalt phthalocyanines were obtained by reaction of 4-(4-tritylphenoxy)phthalonitrile with CuCl₂, ZnCl₂, CoCl₂ metal salts. New compoun

Full text of DOI:10.1080/24701556.2019.1572624

Inorganic and Nano-Metal Chemistry
ISSN: 2470-1556 (Print) 2470-1564 (Online) Journal homepage: https://www.tandfonline.com/loi/lsrt21
Synthesis of novel tetra (4-tritylphenoxy)
substituted metallophthalocyanines and
investigation of their aggregation, photovoltaic,
solar cell properties
Derya Güngördü Solğun, Sabit Horoz & Mehmet Salih Ağırtaş
To cite this article: Derya Güngördü Solğun, Sabit Horoz & Mehmet Salih Ağırtaş (2019):
Synthesis of novel tetra (4-tritylphenoxy) substituted metallophthalocyanines and investigation of
their aggregation, photovoltaic, solar cell properties, Inorganic and Nano-Metal Chemistry, DOI:
10.1080/24701556.2019.1572624
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INORGANIC AND NANO-METAL CHEMISTRY
https://doi.org/10.1080/24701556.2019.1572624
Synthesis of novel tetra (4-tritylphenoxy) substituted metallophthalocyanines
and investigation of their aggregation, photovoltaic, solar cell properties
a
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a
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Derya Gungordu Solgun , Sabit Horoz , and Mehmet Salih Agırtas¸
a
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Department of Chemistry Faculty of Science, Van Yuzuncu Yıl University, Van, Turkey; Faculty of Engineering and Architecture Department
of Electrical and Electronic Engineering, Siirt University, Siirt, Turkey
ABSTRACT
ARTICLE HISTORY
Received 25 October 2018
Accepted 2 January 2019
4-(4-tritylphenoxy) phthalonitrile was synthesized and characterized. Copper, zinc and cobalt
phthalocyanines were obtained by reaction of 4-(4-tritylphenoxy)phthalonitrile with CuCl2, ZnCl2,
CoCl2 metal salts. New compounds were characterized by using electronic absorption, nuclear
magnetic resonance spectroscopy, infrared. The aggregation investigation for phthalocyanine com-
plexes carried out in different concentrations tetrahydrofuran. Copper, cobalt and zinc phthalocya-
nines were used as sensitizers in dye-sensitized solar cell structures (DSSC) by growing on TiO2
coated on FTO (Fluorine doped Tin Oxide) conductive glass substrates. Current density (J) versus
voltage (V) measurements were applied to investigate the photovoltaic properties of the synthe-
sized complexes. The calculated power conversion efficiencies (g%) of the complexes using the
obtained current density (J) versus voltage (V) curves show that these devices can be used as
promising sensitizers in solar cell applications.
KEYWORDS
Characterization; photovol-
taic; phthalocyanine;
synthesis; aggrega-
tion; solubility
Introduction
changing the sensitizers having an important relative value
such as absorbing light in DSSCs.[16]
Today, there is an effort to load new functions into chemical
compounds at the expense of research. Some of the chemi-
cals which have been extensively studied for their new
properties are compounds of phthalocyanine. While phthalo-
cyanine compounds are used as paint in the early days,[1]
today they have application potential in different areas such
as solar cell,[2] chemical sensor,[3] semiconductors,[4] electro-
chromic displaying systems,[5] non-linear optics,[6] laser
dyes,[7] optical storage devices,[8] photodynamic therapeutic
agents (PDT)[9] and liquid crystal.[10] The use of these com-
pounds for dye sensitized solar cell (DSSC) applications is of
interest to researchers. This can contribute to renewable
energy production. Sensitizers that convert incoming energy
to electricity by absorpting the light from the solar energy
used as a source have an effective role in the structure of a
DSSC.[11,12] Ruthenium complexes have been used as prom-
ising sensitizers in DSSCs because of their photoelectron
chemical properties and high stability in the oxidized
state.[13] As an alternative to silicon-based solar cells, DSSCs
have a great interest in photovoltaic applications, with
advantages such as low-cost production and wide applica-
tion areas. Despite these advantages, because the efficiency
of DSSCs is lower than that of silicon-based solar cells, they
have been used on a limited basis in the commercial
field.[14,15] This is why the DSSCs, which have high product-
ivity in parallel with low-cost, need to be fabricated. In this
In the literature, the synthesis of different phthalocya-
nines such as polymeric, oligomeric, ball type, dimeric,
crown ethers has been studied due to their chemical struc-
ture.[17–21] As a natural consequence of this diversity, new
phthalocyanine compounds are synthesized and contribute
to the improvement of the properties of the technological
products they use.[22] It appears that the solubility problems
of the synthesized phthalocyanine compounds are not com-
pletely solved.[23] Existing studies are based on the use of
DSSC of phthalocyanines with electron-withdrawing
groups.[24] Here, it shows that there is a potential for use in
different phthalocyanines. Currently, phthalocyanine com-
pounds with high solubility are needed. Here, the effect of
improving the solubility of the selected substituent group is
present.[25] We have described the synthesis, characteriza-
tion, aggregation, DSSC of phthalocyanines bearing 4-trityl-
phenoxy substituents on the peripheral positions. In this
study designed combination for the synthesis may prevent
the formation of aggregation in organic solvents such as
CHCl3, CH2Cl2, THF, DMF, DMSO, and add interesting
properties to phthalocyanines such as highly solubility.
Moreover, phthalocyanines were used as a sensitizer in
DSSC by growing on TiO2 coated on FTO conductive glass
substrate. Current density (J) versus voltage (V) measure-
ments were applied to investigate the photovoltaic properties
of the synthesized metal phthalocyanines. The calculated
case, it is possible to obtain DSSCs with high efficiency by power conversion efficiency (g%) of the complexes using the
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CONTACT Mehmet Salih Agırtas¸
salihagirtas@hotmail.com
Department of Chemistry Faculty of Science, Van Yuzuncu Yıl University, Van, 65080, Turkey.
Color versions of one or more of the figures in the article can be found online at www.tandfonline.com/lsrt.
ß 2019 Taylor & Francis Group, LLC

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D. GUNGORDU SOLGUN ET AL.
2
obtained current density (J) versus voltage (V) curve shows product was multiply washed successively with water,
that this product can be used as a promising sensitizer in methanol and ethanol. This compound is soluble CH2Cl2,
solar cell application.
CHCl3, THF, toluene, DMF, DMSO. Yield: 0.020 g (32.78%).
UV-Vis) (THF) kmax, nm (log E): 674 (5.21), 608(4.61), 346
(4.93). IR spectrum (cmꢂ1): 3053(C–H aromatic),
1598(C ¼ C), 1490, 1447, 1442, 1230(Ar–O–Ar), 1085, 1050,
1033, 893, 825, 746, 700, 669.
Experimental
General
Copper (II) chloride (CuCl2), zinc (II) chloride (ZnCl2),
Cobalt (II) chloride (CoCl2), Potassium carbonate (K2CO3),
4-tritylphenol, dimethyl sulfoxide (DMSO), N, N-dimethylfor-
mamide (DMF), tetrahydrofuran (THF), chloroform (CHCl3),
1,2-dichloromethane (CH2Cl2), 1,2-dichloroethane (C2H4Cl2)
were purchased from Merck, Sigma and used without further
purification. All reactions were carried out under a dry nitro-
gen atmosphere. Melting points were measured on an electro-
thermal apparatus. Electronic spectra were recorded on a
Hitachi U-2900 Spectrophotometer (Van YYU, Central
Laboratory, Turkey). Routine FT-IR spectra were recorded on
a Thermo Scientific FT-IR (ATR sampling accessory) spectro-
photometer (Van YYU, Central Laboratory, Turkey). 1H
NMR spectra were recorded on an Agilent 400 MHz spec-
trometer (Van YYU, Central Laboratory, Turkey) with tetra-
methylsilane as internal standard. Current density (J) versus
voltage (V) measurement was performed by using PCE-S20
with a monochromatic light source consisting of a 150-W Xe
lamp and a monochromator.
[Tetrakis -(4-tritylphenoxy) phthalocyaninato] Zinc
(II) (5)
A mixture of 4-((4-tritylphenoxy)phthalonitrile 3 (0.059 g,
0.128 mmol) and ZnCl2 (0.014 g, 0.103 mmol) was powdered
in a quartz crucible and heated in a sealed glass tube for
7 min 270 ꢀC. After cooling to room temperature, the prod-
uct was multiply washed successively with water, methanol
and ethanol. This compound is soluble CH2Cl2, CHCl3,
THF, toluene, DMF, DMSO. Yield: 0.023 g (37.70%). UV-
Vis) (THF) kmax, nm (log E): 674 (5.17), 608 (4.51), 350
1
(4.82). H NMR (400 MHz, DMSO-d6): (d: ppm) 8.09, 8.08,
7.82, 7.32, 7.29, 7.21, 7.17, 7.14, 7.11, 3.32, 2.50. IR spectrum
(cmꢂ1): 3053(C–H aromatic) 1593(C ¼ C), 1483, 1442,
1230(Ar–O–Ar), 1215, 1172, 1083, 1035, 1014, 829, 746,
700, 628.
[Tetrakis -(4-tritylphenoxy) phthalocyaninato] Cobalt
(II) (6)
A mixture of 4-((4-tritylphenoxy)phthalonitrile 3 (0.059 g,
0.128 mmol) and CoCl2 (0.014 g, 0.108 mmol) was powdered
in a quartz crucible and heated in a sealed glass tube for
7 min 270 ꢀC. After cooling to room temperature, the prod-
uct was multiply washed successively with water, methanol
and ethanol. This compound is soluble CH2Cl2, CHCl3,
THF, toluene, DMF, DMSO. Yield: 0.024 g (39.34%). UV-
Vis) (THF) kmax, nm (log E): 662 (5.24), 600 (4.72), 328
(5.14). IR spectrum (cmꢂ1): 3055(C–H aromatic),
1598(C ¼ C), 1490, 1467, 1232(Ar–O–Ar), 1166, 1093, 1056,
956, 893, 746, 700.
4 -(4-tritylphenoxy) phthalonitrile (3)
A mixture of 4-nitrophthalonitrile (1) (0.2573 g, 1.486 mmol)
and 4-tritylphenol (2) (0.500 g, 1.486 mmol) in 20 mL dime-
thylformamide (DMF) was stirred at room temperature
under nitrogen atmosphere. After stirring for 15 min, K2CO3
(2 g, 14.5 mmol) was added into the mixture over a period
of 2 h. After stirring the reaction mixture for a further 24 h,
the reaction mixture was poured into water (200 mL) and
stirred. The precipitate was filtered off, washed with water
to neutralize it, then dried under vacuum oven. Yield;
0.640 g (93.12%). The compound is soluble in DMSO, DMF,
THF, CH2Cl2, CHCl3, acetone, acetonitrile. Mp: 224-227 ꢀC.
C33H22ON2:462.54 g/mol. 1H NMR (400 MHz, DMSO-d6):
(d: ppm) 8.11, 8.08, 7.85, 7.43, 7.41, 7.25, 7.21, 7.19, 7.17,
7.16, 7.13, 7.08, 3.34, 2.49. 13C NMR (400 MHz, DMSO-d6):
(d: ppm) 161.16, 152.19, 146.67, 144.17, 136.79, 132.99,
130.89, 128.25, 126.57, 123.40, 122.65, 119.68, 117.17,
115.87(CꢁN), 108.76, 64.54, 40.16. FT-IR spectrum (cmꢂ1):
3051(C–H aromatic), 2231(CꢁN), 1593(C ¼ C), 1566, 1487,
1442, 1288, 1253 (Ar–O–Ar), 1213, 1174, 1082, 1014,
956,885, 825, 750, 700, 632.
The current density (J) – voltage (V)
For J–V measurement, fluorine-doped tin oxide (FTO, 13X
sqꢂ2) conductive glass substrates were used as the photo-
electrodes. The TiO2 paste was coated on the FTO substrates
using the doctor blade method, then sintered at 450 ꢀC for
45 minutes. A certain amount of copper phthalocyanine sus-
pension was dropped on TiO2 coated on FTO conductive
glass substrate. The substrate was dried with N2 gas and
secured against Cu2S counter electrodes containing polysul-
fide electrolytes.
[Tetrakis -(4-tritylphenoxy) phthalocyaninato] Copper
(II) (4)
Results and discussion
A mixture of 4-((4-tritylphenoxy)phthalonitrile 3 (0.059 g,
0.128 mmol) and CuCl2 (0.014 g, 0.105 mmol) was powdered
Synthesis and characterization
in a quartz crucible and heated in a sealed glass tube for The synthetic route and the structures of the 4-(4-tritylphe-
7 min 270 ꢀC. After cooling to room temperature, the noxy)phthalonitrile (3) and metallophthalocyanines (4–6)

INORGANIC AND NANO-METAL CHEMISTRY
3
N
O2
CN
CN
+
OH
1
2
O
CN
CN
3
MCl2
O
N
N
N
M
N
O
N
N
O
N
N
4
5
6
O
M: Cu Zn Co
Scheme 1. The route for the synthesis of compound 3–6.
are shown in Scheme 1. The 4-(4-tritylphenoxy)phthaloni- vibration was observed at 1253 cmꢂ1 After the formation of
trile (3) was accomplished by a base-catalyzed nucleophilic metallophthalocyanines, the “CꢁN” stretching frequency
aromatic nitro displacement reaction between 4-tritylphenol peak disappeared in the IR spectra. The vibration peaks for
1 and 4-nitrophthalonitrile 2 in the presence of dry K2CO3 phthalocyanine 4 observed at 3053 cmꢂ1, “C ¼ C” vibration
in dry DMF under a nitrogen atmosphere for 24 h at room at 1598 cmꢂ1, and “Ar–O–Ar” vibration 1230 cmꢂ1. The
temperature. The phthalocyanine (4) was synthesized by the vibration peaks for phthalocyanine 5 observed at 3053 cmꢂ1
,
reaction of 4-(4-tritylphenoxy)phthalonitrile (3) with CuCl2. “C 5 C” vibration at 1593 cmꢂ1, and “Ar–O–Ar” vibration
Similar to the synthesis of compound 4, the zinc and cobalt 1230 cmꢂ1. For this compound, a shift is observed in the
salts were changed and phthalocyanine compounds 5–6 “C ¼ C” IR peaks while the other peaks show the same
were obtained. The complexes were washed with different value. The vibration peaks for phthalocyanine 6 observed at
solvents and their purity was checked by TLC. The charac- 3055 cmꢂ1, “C ¼ C” vibration at 1598 cmꢂ1, and “Ar–O–Ar”
terization of the new compounds was achieved by the com- vibration 1232 cmꢂ1
.
1
The structure of compound 3 is confirmed by H NMR
for the 4-(4-tritylphenoxy)phthalonitrile through aromatic
bination of several spectroscopic methods, including FT-IR,
1H NMR, and UV–vis spectra.
1
In the IR spectrum of 3, the characteristic “CꢁN” vibra- ring protons in its respective regions. In the H NMR spec-
tion was observed at 2231 cmꢂ1, the aromatic and aliphatic trum of compound 3 in DMSO-d6, aromatic protons appear
“C–H” peaks was observed at 3051 cmꢂ1, “C ¼ C” vibration at 8.11, 8.08, 7.85, 7.43, 7.41, 7.25, 7.21, 7.19, 7.17, 7.16,
peaks were observed at 1593 and 1566 cmꢂ1, “Ar–O–Ar” 7.13, 7.08 (Ar–H), 3.34, 2.49. In the 13C NMR spectrum of

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D. GUNGORDU SOLGUN ET AL.
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Figure 1. 1H NMR spectrum of compound 3.
compound 3 in DMSO-d6, aromatic protons appear at band is not affected. The aggregation behavior for com-
pounds 5-6 shows that these compounds act as monomers
in the THF solution. Concentration-dependent changes of
these two compounds are shown in Figures 4 and 5.
Therefore, these complexes can be used potentially for many
applications.
In our current study, compound 4, compound 5 and com-
pound 6 were used as the sensitizer in DSSC structures. The
current density (J) – voltage (V) measurements were applied
to investigate the photovoltaic properties of complexes. The
power conversion efficiencies of the complexes were calcu-
lated using the recorded J–V curves. Power conversion effi-
ciencies (g) are calculated using the following Equation (1).
161.09, 152.25, 146.25,144.03, 136.79, 133.06, 131.02, 128.45,
126.57, 123.50,122.79, 119.82, 117.46, 116.30, 108.51,64.51,
40.16. Figures 1 and 2 show the proton and carbon NMR
spectra of compound 3. 1H NMR measurements of com-
pounds 4 and 6 were excluded due to their paramagnetic
property. The H NMR protons of the zinc phthalocyanine
compound 5 are observed in the range of 8.09–7.11. DMSO-
d6 solvent peaks were observed at 3.32–2.5.
Some information obtained from the aggregation studies
of phthalocyanine compounds reveals the properties of the
structure. It gives information about the structure form and
the interaction with the solvent in the environment. These
features are also necessary for applications. Especially in the
investigation of phthalocyanine complexes, this parameter is
mostly given in the literature. The phthalocyanine com-
pounds can be monitored in UV spectral data for the sever-
ity of the characteristic Q band.[26,27] Electronic absorptions
spectroscopy has been extensively used to determine the for-
mation of Pc aggregation. In this study, the aggregation
behaviors of 4 were also investigated at different concentra-
tions in THF (Figure 3). Synthesized copper phthalocyanine
compound 4 exhibited a quite good solubility in THF.
Phthalocyanine compound 4 did not show aggregation
behavior at studied concentration ranges in THF. The con-
1
Pm JSCVOCFF
g ¼
¼
(1)
Pin
Pin
Where Pm: maximum output power density, Pin: power
density of incoming light, JSC: short circuit current
density,VOC: open circuit voltage, FF: fill factor. The FF can
be obtained from the relation is given in Equation (2).
JmpVmp
Pm
FF ¼
¼
(2)
JSCVOC JSCVOC
Where Jmp: the current corresponding to the maximum
power point andVmp: the voltage corresponding to the max-
imum power point. The recorded J–V curves for compound
centration-dependent aggregation study shows that the Q 4, compound 5 and compound 6 are revealed in Figure 6.

INORGANIC AND NANO-METAL CHEMISTRY
5
Figure 2. 13C NMR spectrum of compound 3.
Figure 4. Aggregation study of compound 5 in THF.
Figure 3. Aggregation studies of compound 4 in THF.
Table 1 indicates the obtained JSC, VOC and g(%) values
for compound 4, compound 5 and compound 6, respect-
ively. The observed high g% values for each complex can be
assigned with the high a number of electrons which are
injected into a conduction band of TiO2 from the excited
dye of compound 4, compound 5 and compound 6. Because
it is known well that an increase in number of injected elec-
complexes have a wide absorption spectral responses which
lead to producing more photogenerated excitons in free
charge carriers. Hence, this situation results in an increase
in JSC value. Thus, it can be said that JSC and VOC values
play an important role to improve the efficiency of com-
pound 4, compound 5 and compound 6 based DSSC struc-
ture. Furthermore, our result suggests that that these
trons into TiO2 causes an improvement in the electron complexes can be used as a promising sensitizer in dye-sen-
injection efficiency and an increase in VOC. Moreover, the sitized solar cell technology.

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References
[1] Hakeim, O. A.; Diab, H. A.; Adams, J. Preparation and
Characterization of UV Curable-Encapsulated Phthalocyanine
Blue Pigment. Prog. Org. Coat 2015, 84, 70–78. DOI: 10.1016/
j.porgcoat.2015.02.007.
€
[2] Topuz, B. B.; Gu€ndu€z, G.; Mavis, B.; C¸olak, U. Synthesis and
Characterization
of
Copper
Phthalocyanine
and
Tetracarboxamide Copper Phthalocyanine Deposited Mica-tita-
nia Pigments. Dyes Pigm. 2013, 96, 31–37. DOI: 10.1016/
j.dyepig.2012.06.010.
€
ꢀ
ꢀ
[3] Agırta¸s, M. S.; Altındal, A.; Salih, B.; Saydam, S.; Bekaroglu, O.
Synthesis, Characterization, and Electrochemical and Electrical
Properties
of
Novel
Mono
and
Ball-type
Metallophthalocyanines with Four 9,9-bis(4-hydroxyphenyl)-
fluorene. Dalton Trans. 2011, 40, 3315–3324. DOI: 10.1039/
c0dt01575j.
[4] Ai, X.; Lin, J.; Chang, Y.; Zhou, L.; Zhang, X.; Qin, G. Phase
Modification of Copper Phthalocyanine Semiconductor by
Converting Powder to Thin Film. Appl. Surf. Sci. 2018, 428,
788–792. DOI: 10.1016/j.apsusc.2017.09.146.
Figure 5. Aggregation study of compound 6 in THF.
[5] Solis, C.; Baigorria, E.; Milanesio, M. E.; Morales, G.; Durantini,
E. N.; Otero, L.; Gervaldo, M. Electrochemical Polymerization
of EDOT Modified Phthalocyanines and Their Applications as
Electrochromic Materials with Green Coloration, and Strong
Absorption in the near-IR. Electrochim. Acta 2016, 213,
594–605. DOI: 10.1016/j.electacta.2016.07.086.
[6] Aꢀgırta¸s, M. S.; Karata¸s, C.; Gu€mu€¸s, S. Synthesis, Aggregation
Behavior,
Metallophthalocyanines
and
Electronic
with
Properties
2-Isopropyl-5-methylphenoxy
of
Some
Substituents. Z. Anorg. Allg. Chem. 2015, 641, 1334–1339. DOI:
10.1002/zaac.201500121.
[7] Leznoff, C. C.; Lever, A. B. P. Phthalocyanine Properties and
Application, vol. 4; VCH Publisher: New York, 1996.
[8] Li, F.; Zheng, Q.; Yang, G.; Dai, N.; Lu, P. Optical Limiting
Properties of Two Phthalocyanines Using 1064-nm Laser in
Solution. Mater. Lett. 2008, 62, 3059–3062. DOI: 10.1016/
j.matlet.2008.01.135.
ꢀ
[9] Kantekin, H.; Yalazan, H.; Kahriman, N.; Ertem, B.; Serdaroglu,
V.; Pi¸skin, M.; Durmu¸s, M. New Peripherally and Non-periph-
erally Tetra-substituted Metal-free, Magnesium (II) and Zinc
(II) Phthalocyanine Derivatives Fused Chalcone Units: Design,
Synthesis, Spectroscopic Characterization, Photochemistry and
Photophysics. J. Photochem. Photobiol. A 2018, 361, 1–11. DOI:
10.1016/j.jphotochem.2018.04.034.
Figure 6. The recorded J–V curve for compounds 4–6.
Table 1. The obtained JSC, VOC and g(%) values for compound 4, compound
5 and compound 6, respectively.
Samples (Complexes)
JSC (mA/cm2)
VOC (V)
g(%)
[10] El-Nahass, M. M.; Afify, H. A.; Gadallah, A. S.; Hassanien,
A. M.; Atta Khedr, M. Effect of Thermal Annealing on
Structural and Optical Properties of Titanyl Phthalocyanine
Thin Films. Mater. Sci. Semicond. Process 2014, 27, 254–260.
DOI: 10.1016/j.mssp.2014.06.028.
Compound 4
Compound 5
Compound 6
5.99
4.96
5.48
0.56
0.58
0.49
1.77
1.51
1.43
[11] Schulze, T. F.; Schmidt, T. W. Photochemical up Conversion:
Present Status and Prospects for Its Application to Solar Energy
Conversion. Energy Environ. Sci. 2015, 8, 103–105. DOI:
10.1039/C4EE02481H.
[12] Cecconi, B.; Manfredi, N.; Montini, T.; Fornasiero, P.; Abbotto,
A. Dye-sensitized Solar Hydrogen Production: The Emerging
Role of Metal-free Organic Sensitizers. Eur. J. Org. Chem. 2016,
2016, 5194–5215. DOI: 10.1002/ejoc.201600653.
Conclusions
As a result, (4-tritylphenoxy) substituted copper, zinc and
cobalt phthalocyanines and its starting material were
obtained with high yield by an economical method. These
novel compounds were characterized by spectroscopic data
such as IR, UV-Vis and NMR. Aggregation and J-V meas-
urements of the phthalocyanine compounds were performed. [13] Qin, Y.; Peng, Q. Ruthenium Sensitizers and Their Applications
in Dye-sensitized Solar Cells. Int. J. Photoenergy 2012, 2012,
1–21. DOI: 10.1155/2012/291579.
[14] Selvaraj, P.; Baig, H.; Mallick, T. K.; Siviter, J.; Montecucco, A.;
The measurement results show that the copper, zinc and
cobalt phthalocyanines compound can be used in dye-sensi-
tized solar cell technology.
Li, W.; Paul, M.; Sweet, T.; Gao, M.; Knox, A. R.; Sundaram, S.
Enhancing the Efficiency of Transparent Dye-sensitized Solar
Cells Using Concentrated Light. Sol. Energy Mater. Sol. Cells
2018, 175, 29–34. DOI: 10.1016/j.solmat.2017.10.006.
Funding
[15] Ganesan, P.; Yella, A.; Holcombe, T. W.; Gan, P.; Rajalingam,
ꢀ
Author (Agırta¸s) thanks to Van Yuzuncu Yıl University Office of
R.; Al-Muhtaseb, S. A.; Gratzel, M.; Nazeeruddi, M. K. Unravel
the Impact of Anchoring Groups on the Photovoltaic
Performances of Diketopyrrolopyrrole Sensitizers for Dye-
Scientific Research Projects for the financial support to his research
laboratory (FAB-2018-7513).

INORGANIC AND NANO-METAL CHEMISTRY
7
€
_
ꢀ
ꢀ
Sensitized Solar Cells. ACS Sust. Chem. Eng. 2015, 3, [22] Agırta¸s, M. S.; Solgun, D. G.; Ozdemir, S.; Izgi, M. S. Synthesis
2389–2396. DOI: 10.1021/acssuschemeng.5b00332.
[16] Lin, J.; Chen, J.; Chen, X. High-efficiency Dye-sensitized Solar
Cells based on Robust and Both-end-open TiO2 Nanotube
Membranes. Nanoscale Res. Lett. 2011, 6, 475–480. DOI:
10.1186/1556-276X-6-475.
of Tetra 3,4-dimethoxyphenethoxy Peripheral Substituted
Metallophthalocyanines and Investigation of Some Properties.
Chem. Select. 2018, 3, 3523–3528. DOI: 10.1002/slct.201703122.
[23] Cabir, B.; Aꢀgırta¸s, M. S.; Duygulu, E.; Yuksel, F. Synthesis of
Some Metallophthalocyanines Bearing 9-phenyl-9H-fluoren-9-
yl) oxy Functional Groups and Investigation of Their
Photophysical Properties. J. Mol. Struct. 2017, 1142, 194–199.
DOI: 10.1016/j.molstruc.2017.04.060.
[17] Zhao, P.; Wang, Z.; Chen, J.; Zhou, Y.; Zhang, F. Nonlinear
Optical and Optical Limiting Properties of Polymeric Carboxyl
Phthalocyanine Coordinated with Rare Earth Atom. Opt. Mater.
2017, 66, 98–105. DOI: 10.1016/j.optmat.2017.01.029.
[18] Vijayanathan, V.; Venkatachalam, S.; Krishnamurthy, V. N.
Oligomeric Metallo Phthalocyanine-incorporated Conducting
Polymers. Synth. Met. 2000, 114, 273–278. DOI: 10.1016/S0379-
6779(00)00247-2.
ꢁ
ꢁ
[24] Gomis, L. M.; Parejo, C.; Alvarez, J. C.; Lazaro, F. F.; Santos,
ꢁ
A. S. Dye Sensitized Solar Cells (DSSCs) based on Bulky Tert-
octylphenoxycarboxyphenyl
Substituted
Phthalocyanine
Without the Presence of co-Adsorbents. Inorg. Chim. Acta
2017, 468, 327–333. DOI: 10.1016/j.ica.2017.07.043.
€
[19] Yazıcı, A.; Sarıc¸ic¸ek, B.; Altındal, A.; Salih, B.; Bekaroꢀglu, O.
Synthesis and Characterization, Electrical and Gas Sensing
Properties of N,N’-bis(salicylidene)-1,2-phenylendiamine
Substituted Novel Mono and Ball-type Metallo Phthalocyanines.
Inorg. Chim. Acta 2015, 428, 83–92. DOI: 10.1016/
j.ica.2015.01.027.
[25] Aꢀgırta¸s, M. S. Highly Soluble Phthalocyanines with Hexadeca
Tert-butyl Substituents. Dyes Pigm. 2008, 79, 247–251. DOI:
10.1016/j.dyepig.2008.03.004.
[26] Cong, F.; Wei, Z.; Huang, Z.; Yu, F.; Liu, H.; Cui, J.; Yu, H.;
Chu, X.; Du, X.; Xing, K.; Lai, J. Characteristic Absorption
[20] Peng, Y. R.; Cao, Y. H.; Chen, P. F.; Huang, X. X. Synthesis of
di-m-oxo-tetra-(a-pentyloxy) tin(IV) Phthalocyanine. Chin.
Chem. Lett. 2008, 19, 273–276. DOI: 10.1016/j.cclet.2007.12.020.
[21] Liu, Q.; Wang, J.; Liu, D.; Li, R.; Peng, T. Photosensitization of
Zinc Phthalocyanine Bearing 15-crown-5 Ether Moieties on
Carbon Nitride for H2 Production: Effect of co-existing Alkali
Metal Ions. J. Power Sources 2018, 396, 57–63. DOI: 10.1016/
j.jpowsour.2018.05.098.
Band
Split
of
Symmetrically
Tetra-octyloxy
Metal
Phthalocyanines. Dyes Pigm. 2015, 120, 1–7. DOI: 10.1016/
j.dyepig.2015.03.034.
[27] Kubiak, R.; Dyrda, G.; Ejsmont, K. Deduction of the Oxidation
Degree of the Group A15 Elements at the Phthalocyanines on
the Basis of the Q Band. Dyes Pigm. 2017, 145, 371–375. DOI:
10.1016/j.dyepig.2017.06.022.