Synthesis, solar cell application, and biological study of vinyl substituted isophorone derivatives

Article abstract of DOI:10.1007/s11164-019-03924-y

In this study, isophorone derivatives, which are single step aldol products, were designed and synthesized. Our overview of the synthesis of solar cell application and biological applications of series vinyl substituted isophorone compounds is reported. A

Full text of DOI:10.1007/s11164-019-03924-y

Research on Chemical Intermediates
https://doi.org/10.1007/s11164-019-03924-y
Synthesis, solar cell application, and biological study
of vinyl substituted isophorone derivatives
Zehra Kozak1 · Selin Pıravadılı Mucur2 · Betül Canımkurbey3,6 · Önder İdil5 ·
Serpil Eryılmaz4 · Melek Gul1,6
Received: 11 February 2019 / Accepted: 25 June 2019
© Springer Nature B.V. 2019
Abstract
In this study, isophorone derivatives, which are single step aldol products, were
designed and synthesized. Our overview of the synthesis of solar cell application
and biological applications of series vinyl substituted isophorone compounds is
reported. All synthesized compounds were characterized both through experimen-
tal techniques and calculations with density functional theory. Additionally, we
investigated the photophysical properties of small organic compounds for organic
bulk heterojunction photovoltaic cells. The solar cell efciency results were com-
pared and compound 4 was found to be more efcient than the other compounds.
It was found that the optical quantum yield values were very close. Isophorone
derivatives showed better antioxidant activities, which were DPPH, metal chelat-
ing, reducing activity, and antimicrobial activities against Salmonella typhimurium,
Klebsiella pneumonia, Candida albicans, Staphylococcus aureus, Bacillus subtilis,
and Escherichia coli. Compound 7 (which is substituted quinoline) and compound
5 (which is substituted cyno) had the highest antioxidant efect. The 4-brom phenyl,
4-cyno phenyl were used against gram negative bacteria and the 4-ter-butyl phenyl
group was indicated for gram positive bacteria and yeast.
Keywords Aldol · Isophorone · Organic photovoltaics
Introduction
Organic electronics plays important roles in economic and environmental sys-
tems. Organic bulk heterojunction photovoltaic (PV) cells have awoken interest as
an alternative to crystalline silicon solar cells due to their low cost, fexibility, and
Electronic supplementary material The online version of this article (https://doi.org/10.1007/s1116
4-019-03924-y) contains supplementary material, which is available to authorized users.
*
Melek Gul
melek.gul@amasya.edu.tr
Extended author information available on the last page of the article
Vol.:(0123456789)
1 3

Z. Kozak et al.
light weights. To date, various organic compounds have been synthesized for suit-
able PV materials, such as carbazole [1–3], fullerene [4–6] and graphene deriva-
tives [7–9]. Recently, owing to their diverse structure, fexibility, solubility, stabil-
ity and diferent good fuorescence properties, PV cells have been developed and
have shown potential for use as inorganic light emitting diodes (OLED), organic
feld efect transistors (OFET), and bioelectronics devices. Their highest occupied
molecular orbital-lowest unoccupied molecular orbital (HOMO–LUMO) energy and
also band gap properties make organic-based PV materials good candidates for use.
When we changed the substituents, diferent HOMO–LUMO levels were observed,
so we obtained suitable material for OPV device.
In this study, we investigated the photophysical properties of organic small com-
pounds for organic solar cells. We synthesized single step aldol products, including
a conjugated enone system. Aldol reaction generated with isophorone and (het)aro-
matic aldehyde compounds. We obtained a vinyl-substituted whole conjugate sys-
tem. The choice of diferent electronic properties is crucial for substitute aromatic
aldehyde because the targeting compounds should change the electronic proper-
ties and should therefore be attached to electron donating-withdrawing groups, and
hydrogen bonding capability groups linkers. In particular, quinoline derivatives have
photophysical potential as blue photoemitting fuorescence [10]. The oxidation and
reduction potential determined using cyclic voltammetry, solvatochromic efect via
ultraviole-visibly spectrophotometry, quantum yield calculation by fuorescence
spectrophotometry, dipole moment, frontier molecular orbitals energy level, nonlin-
ear optical properties (NLO) and optimization of compounds via density functional
theory (DFT), can be members of photophysical properties, which is interesting in
organic electronics. In this study, a series of vinyl-substituted isophorone derivatives
were designed and synthesized. All synthesized compounds were characterized both
1
by experimental techniques by H-NMR, 13C NMR, MS, X-ray, and DFT calcula-
tions. Their optoelectronic activities were scrutinized using cyclic voltammetry, fu-
orescence quantum yield, and solvatochromic efect with the establishment of their
structure–activity relationships. The continuation of our work is planned to examine
the antimicrobial and antioxidant activities of synthesized compounds.
Experimental
Materials
All reagents and solvents were purchased from Merck and used following further
purifcation of solvents. Melting points were recorded on a Thermo Scientifc Barn-
stead/Electrothermal Apparatus without correction.
Synthesis
Isophrone (2.1 mmol) was added into the solution of appropriate aldehyde (1 mmol)
in ethanol. The methanolic 10 M NaOH solution was added drop-wise at room
1 3

Synthesis, solar cell application, and biological study of…
temperature. After 12 h, the reaction mixture was evaporated and the resulting resi-
due was then purifed by column chromatography [11].
Computational
The theoretical analyses of compounds 1–8 were carried out using DFT/B3LYP/6-
31G(d,p) with the Gaussian 09W software and Gauss View 5.0.9 graphical inter-
face programs [12, 13]. The theoretical approaches were used for the calculations
of some electronic properties related to structure, such as frontier molecular orbitals
energy values, dipole moment, and NLO characterization. These are related to the
photo-physical properties of compounds [14–16]. Furthermore, chemical proper-
ties of the compounds were analyzed through electronegativity, chemical potential,
chemical softness-hardness and total dipole moment.
Determination of photophysical properties
Absorption: The molar absorptivity and maximum absorption wavelength, as well
as the absorption spectra, were obtained from the diferent media. Solutions were
prepared using diferent dielectric constants solvents: toluene (2.38), tetrahydrofuran
(THF) (7.58), methyl alcohol (MeOH) (32.7) and N,N-dimethylformamide (DMF)
(36.7) [17]. For compounds 1–8 the concentration of the solutions ranged from
1.0×10−1 M to 1×10−7 M in toluene, THF, MeOH, and DMF.
Fluorescence
The study was performed to determine the emission spectra, wavelength, and opti-
cal relative quantum yield in DMF and toluene solvents. Relative quantum yield was
calculated using Eq. 1. Tryptophan was selected as a standard compound because its
absorption wavelength is suitable for the comparing compounds 1–8 in 1×10−4
M
toluene solvent [18–20].
(
) (
) (
)
2
ꢀf = ꢀr If ∕Ir . Ar∕Af . nf ∕n ,
(1)
where I is Integrated fuorescence intensity, A absorbance at excitation wavelength,
n refractive index of solvent, r standard, and f is the sample.
Electrochemical properties
Cyclic voltammograms were recorded on the Gammry-References 3000 series with
reference, counter and working electrodes as Ag/AgCl, Pt, and glassy-carbon elec-
trode, respectively. All compounds and standards were examined with 10−4 M solu-
tion in 1,2-dichlorobenzene/acetonitrile/0.1 M Bu4NPF6 solution as the supporting
electrolyte [21, 22].
1 3

Z. Kozak et al.
Fabrication of organic solar cell
Patterned ITO-coated glass substrates were cleaned ultrasonically in acetone, deion-
ized water and ethanol, in turn. Glass substrates were dried with N2 (99.999%
purity). Ozone plasma treatment (50 W, plasma etch) was applied to all the sub-
strates for 5 min for surface cleaning of the patterned ITO substrates. PEDOT:PSS
was fltered through a 0.45 µm membrane PVDF flter. The PEDOT: PSS (PH500)
layer used as hole transport layer (HTL) (~60 nm), was spin-coated onto the ITO
substrates at 2000 rpm for 60 s and then annealed at 120 °C for 20 min in the ambi-
ent atmosphere. N-type semiconductor acceptor material phenyl-C61-butyric acid
methyl ester (PC61BM, Sigma Aldrich with 99.995%) and donor material poly(3-
hexylthiophene) (P3HT, 96.6%, Ossila Ltd.) (Sigma Aldrich with 99.995%, were
frst dissolved in 1,2-dichloroenzene with 10 mg/ml concentration separately and
stirred for 2 h at 50 °C. The two pristine solutions were then blended to make a
solution and were left to mix overnight at 50 °C. The CX guest materials were also
prepared in 1,2-dichloroenzene with 10 mg/ml concentration. They were then pre-
pared with the concentration ratio of D:A:G (1:1:1) mixed for 1 day. The mixture of
this D:A:G was used as an active layer of the solar cell, and it was fltered through
a 0.45 µm PTFE membrane flter and spin-coated on HTL at 1200 rpm for 40 s.
The flms were annealed at 110 °C for 10 min to obtain the proper morphology.
Finally, Ca (15 nm) and Al (~100 nm) were evaporated for the cathode electrode
of the devices. The deposition rate of Ca and Al were maintained at 0.1 nm/s and
2.0 nm/s, respectively. During metal thin flm depositions, the chamber pressure was
kept under 3×10−6 mbar. Electrical characterizations of the devices were done in
the glove-box system (O2 <0.1 ppm, H2O<0.1 ppm). The current density–voltage
(J–V) characteristics of the devices were recorded under standard solar irradiation
(AM 1.5, 100 mW/cm2) using a Xenon lamp as a light source and dark J–V charac-
teristics computer-controlled voltage–current Keithley 2600 source meter at 25 °C.
Biological activity assay
Antioxidant assay
DPPH radical‑scavenging assay
The antioxidant activity of compounds 1–8 were analyzed for scavenging properties
to the 1,1-diphenyl-2-picryl-hydrazil (DPPH·). After 30 min of incubation at room
temperature, samples and control were read spectrophotometrically at 515 nm using
a microplate reader. The Blois method [23–25] assay mixture contained 3.0 ml of
samples at 100 µg/ml ethanol, and 1.0 ml of 0.1 mM DPPH ethanolic solution.
(
)
DPPH Radical Scavenging (%) = AC − AS ∕AC × 100,
where AC is the absorbance of control and AS the absorbance of the samples and
standards.
1 3

Synthesis, solar cell application, and biological study of…
Metal chelatting
The metal chelating activity was evaluated in accordance with the method of Dinis [26,
27]. Samples found in 100 µg/ml in 0.4 ml were added to 0.05 ml FeCl2 (2 mM in
distilled water), and 0.2 ml ferrozine (5 mM in distilled water). After being shaken for
10 min at room temperature, the fnal volume was adjusted 4 ml via ethanol. Absorb-
ance was measured as 562 nm spectrophotometrically with a plate reader.
(
)
Metal Chelating (%) = AC − AS ∕AC × 100,
where AC is the absorbance of control and AS the absorbance of the samples and
standards.
Reducing power
To assess the reducing capacity of samples, Yen and Chen’s [28, 29] methods were
adapted to microvolumes using a microplate reader. The 70 µl sample solution and 35
µl of potassium ferricyanide were added before incubation was carried out for 20 min at
50 °C. 35 µl distilled water, TCA (33 µl, 10%), and 27 µl 0.1% FeCl3 were added to the
sample mixture. After 10 min incubation, absorbance was read at 700 nm.
Antimicrobial assay
Antimicrobial activity studies were performed according to the Minimum Inhibitory
Concentration (MIC) method [30, 31]. In this study, Salmonella typhimurium CCM
5445 (St.), Klebsiella pneumoniae ATCC 700603 (Kp.), Candida albicans ATCC
10231 (Ca.), Staphylococcus aureus ATCC 6538P (Sa.), Bacillus subtilis IMG 22 (Bs.),
and Escherichia coli ATCC 25922 (Ec.) were used. All microorganisms were grown at
37 °C for one night and then suspended in 50 ml of nutrient broth. The resulting sus-
pensions were adjusted to 0.5 McFarland turbidity standards [32]. The compounds 1–8
were dissolved in DMSO and added onto the microorganisms transferred to the tubes at
appropriate concentrations. All the test cultures were grown at 37 °C in incubator. The
last tube where no growth was seen was determined as the MIC value.
Results and discussion
Chemistry
We obtained attachment of an aromatic group containing molecules of interest
through a conjugated system (Scheme 1). We synthesized eight aldol products for
evaluation of their photo-physical properties. All vinylic groups geometry were (E),
which were decided with NMR spectra and X-ray results [11].
UV–Vis absorbance spectra with maximum absorbance–wavelength were
between 316 and 354 nm in toluene (Table 1). Moreover, we note that the maximum
absorbance–wavelength of compounds 7 and 8 red-shifted compared to 1, 2 and 3:
1 3

Z. Kozak et al.
Scheme 1 Synthesis route for compounds 1–8
354(8)<344(7)<322(2)<318(1)<316(3) respectively. Thiol and quinoline groups
caused the extended efective conjugation [33–35]. In the literature, when hypo-
crellin A derivatives were analysed for synthesis and characterization, the UV–Vis
spectra showed maximum absorption wavelength without substituted hypocrellin of
approximately 499 nm, but the S-alkyl derivatives was 508 nm, similar to our com-
pound 8 (Fig. 1) [36].
On the other hand, we changed the solvent system compounds, showing that
the solvatochromic efect depended on the solvent polarity, dielectric constant and
ability for hydrogen bonding to occur. Although the THF solvent indicated a hyp-
sochromic shift, MeOH and DMF had a batochromic shift. Compounds 7 and 8
had hydrogen bonding ability so included OH groups, and SCH3 unit thus showed
more bathochromic shift than others. Molar absorptivities of the compounds in
four diferent solvents, toluene, THF, MeOH, and DMF, were calculated using the
Lambert–Beer law at controlled room temperature. Fluorosolvatochromic efect
was analysed in quinoline derivatives, the results were that the moderated color
Table 1 The compounds 1–8 molar absorption coefcients at the maximum wavelengths, ε (dm3 molcm)
(λ/nm), and quantum yields
Com-
Toluen
THF
MeOH
DMF
Φf
pounds/
solvent
1
2
3
4
5
6
7
8
7503.0 (318 nm)
6406.0 (322 nm)
6577.6 (316 nm)
5762.4 (327 nm)
6027.8 (323 nm)
6240.2 (327 nm)
7511.6 (344 nm)
6668.3(354 nm)
7354.1 (315 nm)
6278.9 (324 nm)
5346.5 (315 nm)
3786.1 (326 nm)
5724.0 (321 nm)
5932.8 (328 nm)
6364.9 (342 nm)
3763.5 (352 nm)
5704.8 (324 nm)
5552.4 (329 nm)
6718.8 (319 nm)
5354.7(334 nm)
5029.9(323 nm)
4062.4(332 nm)
7255.1(341 nm)
6205.7(358 nm)
4092.6 (321 nm)
3494.2 (327 nm)
6543.8(318 nm)
5562.6(329 nm)
5689.6(325 nm)
4988.9(328 nm)
6547.5(351 nm)
6870.7(348 nm)
0.243
0.239
0.234
0.241
0.215
0.217
0.265
0.250
1 3

Synthesis, solar cell application, and biological study of…
0.7
0.6
0.5
0.4
0.3
0.2
0.1
0
250
200
150
100
50
0.7
0.6
0.5
0.4
0.3
0.2
0.1
0
250
200
150
100
50
Emission
Emission
8
5
Excitation
Absorption
Excitation
Absorption
0
0
320
340
360
380
400
300
350
Wavelength (nm)
400
Wavelength (nm)
Fig. 1 Emission, excitation, and UV–Vis absorption spectra of the compounds 5 and 8
shifted, especially in n-heptane and the DMSO solvent system [37]. We compared
this result to our compounds: as a result of toluene and DMF solvents absorption
wavelengths were diferent depending on the solvatochromic efect.
Molar absorptivity, which is a characteristic quantity of atomic or molecular
systems, changes with the wavelength of the radiation [38–40]. The highest molar
absorptivity value was 7511 (dm3 mol cm) (λ/nm) in toluene for compound 7, and
the lowest was 3494 (dm3 mol cm) (λ/nm) in DMF for compound 2.
Electrochemical analyzes were made to calculate the HOMO–LUMO levels
and gap energies (Egap) from oxidation and reduction potentials [41] (Fig. 2). Not
only the cyclic voltammetry calculations but also optical and theoretical results
are summarized in Table 2. The band gap energy was decreased in compounds 7
and 8, and there was thus extra-conjugation.
Figure 3 displays the optimized molecular structure of compounds 1–8 via
B3LYP/6-31G(d,p) levels. To understand the photophysical properties, the FMOs
energy levels and gap, dipole moment, chemical properties and NLO properties
were analyzed via DFT.
Fig. 2 Cylic voltammograms of compounds 5 and 8
1 3

Z. Kozak et al.
Table 2 Comparison of the optical band gap of the compounds 1–8 obtained from CV (Egap), optical
absorption (Eopt) measurements, and theoretical calculations (Et) at eV unit
EOX
ERED
HOMO
LUMO
HOMOT
LUMOT
Egap
Eopt
Et
1
2
3
4
5
6
7
8
−0.892
−0.846
−1.004
−0.932
−0.998
−0.763
−0.825
−0.985
2.183
2.057
2.852
2.525
2.487
1.571
2.174
2.708
−5.312
−5.039
−5.981
−5.548
−5.955
−4.547
−4.914
−5.869
−2.137
−2.014
−2.792
−2.472
−2.872
−1.538
−2.128
−2.651
−6.032
−6.040
−6.097
−5.560
−6.378
−5.800
−5.782
−5.541
−2.262
−2.300
−2.172
−1.923
−2.650
−1.990
−2.430
−2.048
3.175
3.025
3.189
3.076
3.083
3.009
2.786
3.218
3.251
3.225
3.244
3.230
3.095
3.338
2.982
3.225
3.769
3.740
3.925
3.637
3.728
3.810
3.351
3.492
Fig. 3 The optimized molecular structure of title compounds (DFT/B3LYP/6-31G(d,p))
The organic photovoltaic system included two important energy parameters,
which were used to decide which devices were applicable. The frst energy gap
was the donor materials between HOMO and LUMO; the second gap was between
acceptor materials’ LUMO energy level and donor materials’ HOMO energy levels.
We found that the energy level of HOMO was between −6.37 eV and −5.54 eV and
LUMO between −2.65 eV and −1.92 eV, as seen in Table 2. The lowest LUMO
1 3

Synthesis, solar cell application, and biological study of…
energy level was −2.65 in compound 5; −2.43 for compound 7, and −2.04 for com-
pound 8. When we compared these with the band gap, the lowest gap was 3.35 eV
for compound 7, and the highest was 3.92 eV for compound 3. Electron transfer
route was from PEDOT:PSS to P3HT:PCBM, but hole transfer was counter-way.
The PEDOT:PSS polymer system LUMO energy level was −2.4 eV. Only 5 and
7 of synthesized compounds were suitable for electron transfer. We thus noted that
compound 4 should be used in this solar cell device. Global descriptors for elec-
tronegativity, chemical potential, chemical softness-hardness and non-linear optical
properties were calculated. Compound 5 showed the highest electronegativity value.
The values of the frst order hyperpolarizability were compared with urea, and com-
pounds 6, 7, 8 exhibited the very highest NLO character (Table 3). First order hyper-
polarizability of chalcone derivatives, which was included in the enone system, was
calculated by Gopalakrishnan groups: 131 × 10−33 esu [41]. Otherwise, styrene was
used as an NLO monomer for optoelectronic polymers [42].
Biological assay
Antioxidant activities
We tested the antioxidant activities of the compounds, with the aim of discovering
the structure of the relationship between the activities. The compounds exhibited
the highest DPPH activities and the results are compared with synthetic antioxidant
standards of BHT and BHA in Fig. 4. The activity of compound 7 was the highest.
Metal chelating activity was related to transition metals via oxidative stress
reaction. As seen in Fig. 5, the metal chelating activities of compounds 1–8 were
compared to EDTA. The activity depended on the concentration of the com-
pounds. The metal chelating activity values of Fe2+–ferrozine complex were
as follows: 7 > 5 > 8 > 3 > 4 > 2 > 1, and compound 7 had a value of 43.76% in
250 µg/ml concentration.
The reducing activity method was used to identify the reduction of Fe3+ to
Fe2+. Figure 6 shows the reducing activity compared to Trolox and BHA. The
Table 3 The values of electronegativity, chemical potential, chemical softness-hardness, total dipole
moment, mean polarizability, and frst order hyperpolarizability for compounds
Compounds χ (eV)
μ (eV)
S (eV−1
)
η (eV)
μ (D)
〈ꢀ〉(×10−24 esu) ꢀtot
(×10−33 esu)
1
2
3
4
5
6
7
8
0.15242 −0.15242 14.43835 0.06926 3.59378 29.78537
0.15324 −0.15324 14.55151 0.06872 3.51229 31.55476
0.15196 −0.15196 13.86578 0.07212 5.77473 30.65374
0.13751 −0.13751 14.96334 0.06683 6.51162 30.14855
0.16591 −0.16591 14.59747 0.06850 3.49840 29.78537
0.14314 −0.14314 14.28378 0.07001 5.06304 37.14634
0.15091 −0.15091 16.23640 0.06159 2.57860 38.92706
0.13947 −0.13947 15.58118 0.06418 4.05658 37.01766
2878.91
28526.26
13307.12
20159.42
2878.91
33099.67
40436.74
74672.24
1 3

Z. Kozak et al.
DPPH Radical Scavenging Activity
50 μg/ml
100 μg/ml
150 μg/ml
200 μg/ml
250 μg/ml
100
80
60
40
20
0
1
2
3
4
5
6
7
8
BHT BHA
Compounds
Fig. 4 DPPH activities of compounds 1–8 and BHA, BHT as standards
Metal Chelating Activity
50 μg/ml
100.000
80.000
60.000
40.000
20.000
0.000
100 μg/ml
150 μg/ml
200 μg/ml
250 μg/ml
1
2
3
4
5
6
7
8
EDTA
Compounds
Fig. 5 Iron chelating activity of compounds compared to EDTA as standard
Reducing Activity
0.700
0.600
0.500
0.400
0.300
0.200
0.100
0.000
50 μg/ml
100 μg/ml
150 μg/ml
200 μg/ml
250 μg/ml
Compounds
Fig. 6 Reducing capacity of compounds, Trolox, and BHA
highest was 0.375 in compound 7 and the activity related to concentrations was
also important.
Antimicrobial
The antimicrobial work was performed using the MIC method and 3 g negative, 2
g positive and only one yeast were used as microorganisms. We conducted the MIC
study due to determination of aryl and cyclohexanon substitute enone system behav-
iour against some bacteria and yeast. The bis-aromatic ring consisting of enone
compounds was reactive against K. Pneumonia, B. Subtilis, and E. Coli [43, 44].
1 3

Synthesis, solar cell application, and biological study of…
As shown in the Table 4, it was determined that compounds 1 and 5 had consid-
erable efects, especially on gram negatives. When the MIC values for compound 1
were examined, they were 250, 375, 500 μg/ml for gram negative S. typhimurium,
K. pneumonia and E. coli respectively. When compound 5 was investigated, the
MIC values for the same gram-negative bacteria were 500, 500 and 1500 μg/ml,
respectively. In addition, it appeared that compounds 7 and 8 were only efective on
S. typhimurium from among the gram negative bacteria with MIC value of 375 μg/
ml. However, compound 6 was found to have signifcant efects on gram-positive S.
aureus and B. subtilis and yeast C. albicans. The MIC values for gram-positive S.
aureus and B. subtilis were 250, while for C. albicans which was yeast, this value
was found to be 375 μg/ml.
Organic solar cell application results
Figure 7a shows the structure of the solar cell fabricated, together with the band
structure of its components. The charge-separation occurred in heterojunction com-
posite of poly(3-hexylthiophene) (P3HT), [6]-phenyl-C71 butyric acid methyl ester
(PC70BM) and compound layer. Poly(3,4ethylenedioxylenethiophene)-polystylene
sulfonic acid (PEDOT:PSS)was a highly conductive hole transport layer (Table 5).
The energy-level diagram (Fig. 7b) indicates the HOMO energies and LUMO
energies of the individual component materials. The current versus voltage (I–V)
characteristics of bulk heterojunction solar cells with P3HT:PCBM:X under illumi-
nation from solar simulator with irradiation intensity of 300 W/cm2 are shown in
Figs. 8 and 9.
Figure 8 shows the non-ohmic electrical response of I–V characteristics curves
P3HT:PCBM:X (a) X: 4-Br, (b) X:4-Cl, (c) X:4-OCH3, (d) X:4-SCH3 bulk hetero-
junction in dark and in light (300 W Xenon lamp) at room temperature. It was found
that the dark current density of the devices was much smaller than that of the light
current density, which indicated that the charge recombination was increased by
illumination. It was presented our control device with plain P3HT:PCBM data in
Fig. 9a. It can be seen solar cell parameters 4-SCH3 and control device with plain
Table 4 Antimicrobial activity
Compounds Gram-negative
St. Kp.
Gram-positive
Sa. Bs.
Yeast
of compounds 1–8 (MIC in μg/
ml)
Ec.
500
Ca.
1
250
2000 >5000
4000
2000
500
2000 >5000
375
375
375
1500
2000 >5000
1000 >5000
3000 >5000
3000 >5000
3000
2
3
500
2000
4
1000 >5000 >5000
500 1500 >5000
2000 >5000
4000 >5000
5
6
2000
2000
250
250
375
2000
7
2000
1000
2000
2000
8
4000 >5000 >5000 >5000
DMSO
>5000 >5000 >5000 >5000 >5000 >5000
1 3

Z. Kozak et al.
V
-
+
(a)
(b)
Ca/Al
P3HT:PCBM:CX
PEDOT:PSS
Glass/ITO
0.0
-1.0
-2.0
1.5
4.5
2.0
2.1
2.1
2.2
5.2
2.4
2.79
2.65
2.87
2.9
-3.0
-4.0
4.7
-5.0
-6.0
-7.0
-8.0
4.91
5.0
5.3
5.5
5.86
C8
5.98
5.96
C5
Ca/ Al
ITO PEDOT:PSS
C6 C7
C1
C2
C4
C3
Fig. 7 a Solar cell device architecture, b Energy diagrams of materials utilized in solar cell device
Table 5 Solar cell parameters of
Device
Isc
Voc
FF
%n
4-OCH3 and control device with
plain P3HT:PCBM
Compound 4
1.5 * 10−5 mA/cm2
0.54 0.17 1.47 * 10−8
Control device 0.68 * 10−3 mA/cm2 0.6
0.49 2 * 10−6
P3HT:PCBM from inset in Fig. 9a, b, the efciency of the control device is rela-
tive high. The current values increased exponentially with an increase in the forward
bias voltage. The turn-on voltage was around 0.7 V for the forward bias and there
was a reverse bias breakdown voltage of 1.2 V as seen from the I–V curve in the
dark (Fig. 9a).
The devices with compound 4 showed Jsc =5.17 mA/cm2, Voc =0.73 V, FF=0.42.
A ternary organic solar cell is a promising device for improving the power conver-
sion efciency (PCE) of single-junction organic solar cells by broadening the light
absorption spectrum with the incorporation of two electron donors and one accep-
tor or one donor and two acceptors. However, in most cases, the contribution of the
third component to the absorption of light was reduced due to the fact that the third
component was not morphologically compatible [45]. For this reason, although the
ternary solar cell shows around~2% efciency, efciency of our devices are low
(Fig. 10).
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Synthesis, solar cell application, and biological study of…
Fig. 8 I–V characteristics curves P3HT:PCBM:CX a X: 4-Br, b X:4-Cl, c X:4-OCH3, d X:4-SCH3 bulk
heterojunction in dark and in light (300 W Xenon lamp)
Fig. 9 a I–V characteristics curves of control device with plain P3HT:PCBM (The inset displayed the
efect of control device with plain P3HT:PCBM on photovoltaic parameters of polymer solar cells). b
I–V characteristics zoomed curves of compound 4 (The inset displayed the efect of blend P3HT: Com-
pound 4 molecule on photovoltaic parameters of polymer solar cells)
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Z. Kozak et al.
Fig. 10 Control device with
plain P3HT:PCBM
Conclusion
We have reported the synthesis and characterization of isophrone vinyl deriva-
tives. Upon application of these compounds, both the biological activity and solar
cell efciency were scrutinized. Theoretical calculations were used and the exper-
imental results were correlated. Frontier molecular orbitals, band gap energy val-
ues and some chemical properties revealed the biological activity and photovoltaic
properties. Another signifcant result was that enone-substituents infuence not only
physical parameters but also biological activity. Quinoline substituent, which had
the lowest gap value but higher HOMO energy value, revealed a stunning level of
antioxidant activity and antimicrobial activity, whereas solar cell efciency was not
higher than expected. It was shown that compound 4 had the lowest electronegativ-
ity and otherwise the highest chemical softness. So, compound 4 was characterized
as hole transfer material. The lowest efciency was seen in compounds 2 and 3.
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Afliations
Zehra Kozak1 · Selin Pıravadılı Mucur2 · Betül Canımkurbey3,6 · Önder İdil5 ·
Serpil Eryılmaz4 · Melek Gul1,6
1
Department of Chemistry, Faculty of Arts and Sciences, Amasya University, 05100 Amasya,
Turkey
2
Photonic Technologies Laboratory, TÜBİTAK MAM Material Institute, 41470 Gebze, Kocaeli,
Turkey
3
S. Şerefeddin Health Services Vocational School, Amasya University, 05100 Amasya, Turkey
4
Department of Physics, Faculty of Arts and Sciences, Amasya University, 05100 Amasya,
Turkey
5
Department of Science Education, Faculty of Education, Amasya University, 05100 Amasya,
Turkey
6
Central Research Laboratory, Amasya University, 05100 Amasya, Turkey
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