RETRACTED ARTICLE: Pt NPs@GO as a highly efficient and reusable catalyst for one-pot synthesis of acridinedione derivatives

Article abstract of DOI:10.1039/c5ra06441d

Graphene oxide decorated with platinum nanoparticles (Pt NPs@GO) has been used for the first time as a highly stable, exceptionally reusable, isolable, bottleable, long-lived and highly efficient catalyst for the synthesis of acridinedione derivatives from dimedone, aromatic aldehydes and various amines with great catalytic performance. All the acridinedione compounds were synthesized in DMF in a single process through two successive reactions (aldol condensation and Michael addition) in the presence of highly efficient Pt NPs@GO. The synthesized catalyst was characterized by transmission electron microscopy (TEM), high resolution electron microscopy (HRTEM), X-ray diffraction (XRD), atomic force microscopy (AFM) and X-ray photoelectron spectroscopy (XPS). All products obtained using Pt NPs@GO were characterized by FT-IR, ¹H-NMR, ¹³C-NMR and HRMS techniques.

Full text of DOI:10.1039/c5ra06441d

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Pt NPs@GO as Highly Efficient and Reusable Catalyst for One-Pot
Synthesis of Acridinedione Derivatives
Received 00th January 20xx,
Accepted 00th January 20xx
a
†
b
†
Handan Pamuk , Burak Aday , Fatih Şena* and Muharrem Kayaa*
Platinum nanoparticles decorated with graphene oxide (Pt NPs@GO) have been used for the first time as highly stable,
exceptional reusable, isolable, bottleable, long-lived and highly efficient catalyst for the synthesis of acridinedione
derivatives from dimedone, aromatic aldehydes and various amines with great catalytic performance. All acridinedione
compounds were synthesized in DMF a single process through two successive reactions (Aldol condensation and Michael
addition) in the presence of highly efficient Pt NPs@GO. The synthesized catalyst was characterized by transmission
electron microscopy (TEM), the high resolution electron micrograph (HRTEM), X-ray diffraction (XRD), Atomic force
microscopy (AFM) and X-ray photoelectron spectroscopy (XPS). All products obtained by Pt NPs@GO were characterized
by FT-IR, 1H-NMR, 13C-NMR and HRMS techniques.
DOI: 10.1039/x0xx00000x
www.rsc.org/
catalysts, for example Amberlyst-15 [16, 17], CTAB [18], DBSA
[19, 13], FSG-Hf(Npf2)4 [20], H2SO4 [15], Melamine-
Introduction
formaldehyde resin supported H+ [21], Proline [22], SiO2-Pr-
SO3H [23]. However, these homogeneous catalysts pose
difficulties in reusability, recovery, separation and the sythesis
procedure. For this reason, the heterogeneous alternatives
have already captivated much attention. Due to the
heterogeneous catalyst may be recovered and reusable,
recently several heterogeneous catalytic systems were
reported using, for example, CdO [24], Fe2O3@SiO2-PW [25],
Fe3O4 [26], Fe3O4@SiO2 [27], NiFe2O4@SiO2-FHS [28], ZnFe2O4
[29] as catalysts. However the problem in most of those
catalytic systems is unsatisfactory yield, long reaction times,
laborious work-up procedures, the requirement of special
apparatus and harsh reaction conditions. To avoid these
limitations and to improve the reaction conditions available for
the synthesis of acridinedione, the discovery of new
methodologies using new heterogeneous and reusable
catalysts is still in demand. Herein we wish to report an
efficient and novel method for the synthesis of acridinedione
derivatives via one-pot MCRs of aromatic aldehyde, cyclic
diketones, and various aromatic amines in high yields and
short reaction times by using Pt NPs@GO as a highly efficient,
robust, reusable and easily recoverable catalyst for synthesis
of acridinedione derivatives.
Acridinedione molecules were discovered in 19th century and
new derivatives of acridinedione were still continued to be
explored today. Acridinedione derivatives of 1,4-
dihydropyridine are compounds having interesting biological
features which are similar to the structure of Nicotinamide
Adenine Dinucleotide (NADH), an important co-enzyme found
in cells [1]. Moreover, acridinedione derivatives are
medicinally important compounds [2] and are used in laser
dyes due to their high fluorescence efficiency [3, 4].
Furthermore, since acridinedione derivatives have a wide
range of biological activities, for example antimicrobial [5, 6],
antibacterial [7], fungicides [8], antitumor [9], anticancer [10-
12] and also used for glaucoma treatment as carbonic
anhydrase inhibitor [13-15] there are lots of reported methods
for synthesis of acridinedione including multi component
condensation (MCR) of aromatic aldehyde, cyclic diketones,
and various aromatic amines in the presence of different
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Journal Name
ꢃ
ꢃ
ꢃ
ꢁ
ꢂ ꢄꢅ ꢄꢆ
Sin θ = ꢀ
(for a cubic structure)
ꢃꢇ
The current Pt NPs@GO has been used for the first time for
these types of synthesis reactions.
The average crystallite particle size of Pt NPs@GO were found to be
about 3.49 ± 0.53, using the following equation [36-38];
Results and discussion
Pt NPs@GO has been prepared by sonochemical reduction method
ꢍꢎ
ꢈ ꢉꢊꢋ ꢌ
as given experimental section and their preliminary characterization
was performed by TEM, HRTEM, XRD, AFM and XPS methods.
The high resolution electron micrograph (HRTEM) and particle size
histograms of the prepared catalyst are demonstrated in Fig. 1. This
also shows the information regarding the particle size and
morphology of the Pt NPs@GO. A uniform distribution of the
catalyst particles with a relatively narrow range on graphene oxide
support was detected and most of the particles are found to be
with and approximately spherical shape and average diameter of
around 3.25 nm and no agglomerations were observed in the
prepared catalyst. Moreover, the chosen area of HRTEM image of
Pt NPs@GO displays the highly crystalline feature with a spacing of
0.229 nm which is very close to nominal Pt (111) spacing of 0.228
nm [30-35].
ꢏꢐꢑꢒꢓ
Where k= a coefficient (0.9); λ= the wavelength of X-ray used
(1.54056 Ǻ); β= the full width half-maximum of respective
diffraction peak (rad); θ= the angle at the position of peak
maximum (rad). Moreover, the Chemical Surface Areas (CSA) of the
Pt NPs@GO were found to be 88.17 m2/g by the use of the
following equation, assuming homogenously distributed and
spherical particles [39],
6 ꢔ 10ꢕ
CSA ꢌ
ꢖ ꢔ ꢈ
where d is the mean Pt crystalline size in Å (from the XRD results)
and ρ is the density of Pt metal (21.4 g/cm2) [40, 41].
Atomic force microscopy (AFM) was also used to observe the height
diameter distributions shown in Fig. S2a, b. The AFM height
diameter of the Pt NPs@GO is found to be 3.27 nm which is in good
agreement with the dimensions get by XRD and TEM.
X-ray photoelectron spectroscopy (XPS) was used for the
determination of the surface compositions and chemical oxidation
states of Pt in the prepared nanocatalyst. The Pt 4f region of the
Fig. 1. High resolution transition electron micrograph and particle spectrum was analysed, and the fitting of the XPS peak was
size histogram of a Pt NPs@GO
performed using the Gaussian-Lorentzian method. In the XPS
spectrum, accurate binding energies (±0.3 eV) were determined by
referencing to the C 1s peak at 284.6 eV. The Pt 4f photoelectron
spectrum, consisting of two pairs of doublets, is illustrated in Fig. S3
for the prepared catalyst. The most intense doublet at about 71.2
and 74.0 eV is a signature of metallic platinum (23-30) and the
other doublet at about 74.0 and 77.0 eV is most likely caused by a
very small fraction of oxidized Pt4+ species possibly due to PtOx
species formed during catalyst exposure to the atmosphere. The
ratios of Pt (0) to Pt (IV) for the prepared catalyst were calculated
from the relative peak area of the Pt 4f spectrum. The relative
intensities of the Pt (0) and Pt (IV) species were estimated by
calculating the integral of each peak after smoothing and
X-ray diffraction (XRD) measurements indicate that Pt NPs@GO
exhibit distinct diffraction patterns, as illustrated in Fig. S1. The
diffraction peaks at 2θ = 39.74, 46.32, 67.63, 81.58 and 85.79 are
due to Pt (111), (200), (220), (311), and (320), respectively, planes
of the face-centered cubic (fcc) crystal lattice of platinum (JCPDS-
ICDD, Card No. 04-802). The peak at 10.8° is raised from the
graphite (002) plane of GO. The Pt (220) diffraction peaks of the
prepared catalyst are used to calculate the lattice parameters (αPt)
and average crystallite sizes of the metal particles. The lattice
constant was found to be 3.921 Ǻ, which is in good agreement with
3.923 Ǻ for pure Pt, by using the following equation [33].
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subtracting the Shirley-shaped background and Pt (0)/Pt (IV) ratio is effective method has been designed in the presence of Pt NPs@GO.
found to be 6.81 for the Pt NPs@GO.
The synthesis of acridinedione compounds were realized in DMF
from dimedone 1, different aromatic aldehydes 2a-g and various
It is worth mentioning that Pt NPs@GO is often used as a catalyst in amines 3a, b in a single process through three successive reactions
batteries, the hydrogen storage, sensors, super-capacitors [42-46] (Aldol condensation, Michael addition and cyclization) by using Pt
but its use as a catalyst for synthesizing acridinedione derivatives NPs@GO as catalyst. Especially these acridinedione derivatives have
from different aromatic aldehydes and various amines has not been been synthesized by using 1, 2f, 3a compounds in the presence of
reported before.
Pt NPs@GO as a model reaction (Scheme 1).
For the synthesis of acridinedione derivatives new, facile and
Scheme 1. Synthesis of acridinedione derivatives in the presence of Pt NPs@GO.
In this line of work, we compared the results using Pt NPs@GO in We also optimized our model reactions by different solvents,
the synthesis of acridinedione derivatives with those obtained using amount of catalyst and reaction conditions on the basis of different
other catalysts such as DBSA, hydrochloric acid, glacial acetic acid temperatures.
[47], sulfuric acid, ionic liquid [48]. As shown in Table 1, Pt Firstly, the effect of different solvents such as chloroform, solvent-
NPs@GO is the most efficient catalyst which gives the highest yields free, water, acetonitrile, methanol, tetrahydrofuran, dioxane,
of products in the shortest time.
ethanol and dimethylformamide has been evaluated on the
reaction rate under the same reaction conditions (Table 2). Since
the reaction proceeded with the highest yield and shorter reaction
time in the presence of DMF compared to other used solvents, we
have chosen DMF as an optimum solvent for the model reaction.
Table 1. Comparison of Pt NPs@GO with other catalysts
100
90
80
75
70
60
80
6
80
4
82
4
82
93
5
3
1
Time (h)
Yield (%)
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Table 2.
Journal Name
After standardizing the solvent and catalyst concentration, we
A
comparison of the efficiency of various solvents turned our attention toward examining the temperature effect on
employed in the synthesis of the acridinedione derivatives
the model reaction. It was observed that at room temperatures no
desired product was formed even after 48 h of stirring. The yield of
desired product gradually increased with temperature from room
temperature to 75 oC as shown in Table 4.
100
85
70
55
40
93
78
80
75
71
65
60
56
43
0.5
12
Table 4. The Optimization of temperature for preparation of
acridinedione derivatives using Pt NPs@GO as catalyst in DMF
8
6
5
5
4
3
1
150
125
100
75
50
Time (h)
Yield (%)
Time (h)
25
0
We carried out seven sets of model reaction by varying the amount
of catalyst to determine the exact catalyst concentration for the
best possible yield. The first set where no catalyst was used led to
no formation of product but the amount of catalyst increased
gradually from 3 to 8 mg a steady increase was observed in the
product yield (Table 3). Furthermore increase in catalyst
concentration give rise to decrease in the product yield possibly due
to the protonation of amine groups in the aromatic ring by using
carboxylic acid groups of the graphene oxide.
Yield (%)
Temperature (ºC)
1
2
3
4
5
6
1
2
3
3
1
4
1
5
6
1
Time (h)
48
1
Yield (%)
0
85 93 93 93 93
Temperature (ºC)
25 50 75 100 125 150
As a summary, the highest efficiency and fastest reaction time on
the model reaction was observed at 75 oC by using 8 mg of Pt
NPs@GO in DMF. The results of all reactions performed under
these conditions are shown in Table 5.
Table 3. The Optimization of Pt NPs@GO concentration for
preparation of acridinedione derivatives in DMF
100
80
60
40
20
0
Amount of catalyst
Time (h)
Yield (%)
1
2
3
4
5
6
7
1
0
2
3
3
4
8
5
6
7
Amount of catalyst
Time (h)
5
7
10 14 20
0.5 0.5 0.5
24 12
1
Yield (%)
0
40 69 93 91 86 72
Table 5. Synthesis of acridinedione derivatives 4a-j in the presence of 8 mg Pt NPs@GOa
Mp. (oC)
Entry
R
R’
Time(min)
Yieldb (%)
Found
Reported
4a
4b
4c
4d
4e
4f
-H
4-NO2
3-NO2
4-Br
4-Cl
4-Cl
4-Cl
4-Cl
4-Cl
4-Cl
4-Cl
4-Br
4-Br
4-Br
50
75
90
60
60
60
75
60
75
120
94
93
94
95
93
93
96
95
96
94
300-302
315-317
285-287
304-305
280-282
262-265
255-257
303-305
295-296
318-320
309-311 [49]
>300 [50]
285-286 [51]
>300 [50]
>300 [52]
268-269 [51]
269-270 [53]
269-272 [54]
—
4-F
4-CH3
4-OCH3
-H
3-NO2
4-Br
4g
4h
4i
4j
—
a Reactions were carried out with dimedone, aromatic benzaldehyde and various amine, in 2 : 1 : 1 molar ratio.
b Yields refer to isolated pure products.
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All the products were characterized by melting point, FT-IR, NMR, The prepared platinum nanoparticles where mixed in a 1:10 ratio
and HRMS analyses (Fig. S4-13).
with GO which is used as a support.
The efficiency of the catalyst was also checked by investigation of
its reusability. After completion of the reaction, Pt NPs@GO was General procedure for preparation of acridinedione derivatives (4a-
separated, washed with acetone, dried and reused in another set of j) using Pt NPs@GO as the catalyst
reaction. It was observed that the catalyst can be reused for six A mixture of 2 mmol dimedone 1, 1 mmol 4-methyl benzaldehyde
times with very high yields (Table 6). It should be pointed out that 2f, 1 mmol 4-cloroaniline 3a and Pt NPs@GO (8 mg) in 3 ml DMF
no extra care should be taken in order to store or handle the was heated to 75oC continuously for 60 min. The reaction progress
catalyst due to no air or moisture sensitivity. To the best of our was monitored by TLC. The solid product was filtered, washed with
knowledge Pt NPs@GO shows the best reusability performance in 500 ml water, and recrystallized from ethanol (93-96%).
literature [24-29].
10-(4-bromophenyl)-3,3,6,6-tetramethyl-9-(3-nitrophenyl)-3,4,6,7,
9,10-hexahydroacridine-1,8(2H,5H)-dione (4i)
Table 6. Reusability performance of Pt NPs@GO in the model
As yellow crystals, (0.571 g, 96 %), mp. (295-296 oC) (ethanol). 1H-
NMR (300 MHz, DMSO-d6) δ (ppm): 0.70 (s, 6H, 2x-CH3), 0.90 (s, 6H,
2x-CH3), 1.82 (d, 2H, J= 17.47 Hz, -CH2), 2.02 (d, 2H, J= 16.10 Hz, -
CH2), 2.19-2.26 (m, 4H, -CH2), 5.10 (s, 1H, -CH), 7.35-7.40 (m, 2H, Ar-
H), 7.56-7.61 (m, 1H, Ar-H), 7.76-7.86 (m, 3H, Ar-H), 8.00-8.02 (m,
1H, Ar-H), 8.11-8.16 (m, 1H, Ar-H), 7.82 (d, 2H, J= 8.68 Hz, Ar-H);
13C-NMR (75 MHz, DMSO–d6) δ (ppm): 26.56, 29.65, 32.26, 32.45,
41.35, 49.95, 113.07, 119.25, 123.09, 130.33, 131.26, 132.56,
133.53, 138.10, 145.95, 150.74, 195.54; IR (cm–1): 3052 w (Ar-H),
2959 s (-CH), 1635 s (C=O), 1574 s (C=C); HRMS (QTOF-ESI): m/z
calcd. For C29H29BrN2O2: 548.1311: found: 549.1382 ([M+H]+).
reaction.
95
90
93
93
92
91
90
85
88
1
2
3
4
5
6
Yield (%)
Experimental
The preparation of Pt NPs@GO
9,10-bis(4-bromophenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-hexahyd
roacridine-1,8(2H,5H)-dione (4j)
Pt NPs was synthesized by sonochemical reduction method.
Summarizing this method, ethanol and super hydride were used to
reduce the mixture of 0.25 mmol of PtCl4 dissolved in small amount
of dehydrated tetrahydrofuran and 0.25 mmol of octylamine ligand
by the help of ultrasonicator. The observation of a brown-black
colour in the solution indicates the formation of amine-stabilized Pt
NPs. Lastly, in the room temperature, the solid Pt NPs was dried
under vacuum. Graphene oxide (GO) was synthesized from graphite
powder using modified Hummer’s method [Supplementary section].
As yellow crystals, (0.549 g, 94 %), mp. (318-320 oC) (ethanol). 1H-
NMR (300 MHz, DMSO-d6) δ (ppm): 0.70 (s, 6H, 2x-CH3), 0.90 (s, 6H,
2x-CH3), 1.78 (d, 2H, J= 17.13 Hz, -CH2), 2.01 (d, 2H, J= 16.01 Hz, -
CH2), 2.16-2.22 (m, 4H, -CH2), 5.00 (s, 1H, -CH), 7.24-7.44 (m, 6H, Ar-
H),; 13C-NMR (75 MHz, DMSO–d6) δ (ppm): 26.47, 29.61, 32.53,
32.92, 41.34, 49.84, 112.71, 121.50, 122.56, 123.23, 130.21, 133.60,
134.75, 137.95, 147.88, 148.59, 151.32, 195.62; IR (cm–1): 3051 w
(Ar-H), 2954 s (-CH), 1634 s (C=O), 1575 s (C=C); HRMS (QTOF-ESI):
m/z calcd. For C29H29Br2NO2: 581.0565: found: 582.0484 ([M+H]+).
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Conclusions
[10].S.A. Gamage, J.A. Spicer, G.J. Atwell, G.J. Finlay, B.C.
Baguley, W.A. Denny, J. Med. Chem. 1999, 42, 2383-2393.
Easy, effective and practical synthetic method has been
developed for the synthesis of acridinedione cycloaddition
reactions of the various amine, aromatic aldehyde compounds
and dimedone in the presence of highly stable, exceptional
reusable, isolable, bottleable, long-lived and highly efficient Pt
NPs@GO as the catalyst. Pt NPs@GO is the most efficient
catalyst which gives the highest yields of products in the
shortest time. Further, Pt NPs@GO shows the best reusability
performance possible due to no air or moisture sensitivity of
the catalyst. This reusability performance offers advantages
like simple work-up and high yields.
[11].M.G.R. Pitta, E.S. Souza, F.W.A. Barros, M.O.M. Filho, O.
Pessoa, M.Z. Hernandes, M.D.C.A.D. Lima, S.L. Galdino, I.D.R.
Pitta, Med. Chem. Res., 2013, 22, 2421–2429.
[12].K. Venkatesan, S.S. Pujari, K.V. Srinivasan, Synth. Commun.,
2008, 39, 228-241.
[13].M. Kaya, E. Basar, E. Çakir, E. Tunca, M. Bulbul, J. Enzyme
Inhib. Med. Chem., 2012, 27, 509-514.
[14].R. Ulus, İ. Yeşildağ, M. Tanc, M. Bülbül, M. Kaya, C.T.
Supuran, Bioorg. Med. Chem., 2013, 21, 5799-5805.
[15].İ. Yeşildağ, R. Ulus, E. Basar, M. Aslan, M. Kaya, M. Bülbül,
Monatsh. Chem., 2014, 145, 1027-1034.
Acknowledgements
[16].B. Das, P. Thirupathi, I. Mahender, V.S. Reddy, Y.K. Rao, J.
Mol. Catal. A: Chem., 2006, 247, 233-239.
This research was financed by Dumlupınar University Research
Fund (Grant No. 2014-62 and 2014-05) as well as by the
Dumlupınar University ILTEM research laboratory. The partial
supports by Science Academy are gratefully acknowledged.
[17].M. Kaya, Y. Yıldırır, G.Y. Çelik, Med. Chem. Res., 2011, 20
,
293–299.
[18].J.J. Xia, K.H. Zhang, Molecules, 2012, 17, 5339-5345.
[19].T.S. Jin, J.S. Zhang, T.T. Guo, A.Q. Wang, T.S. Li, Synlett,
2004, 12, 1425–1427.
Notes and references
‡ These authors contributed equally to this work.
[20].M. Hong, G. Xiao, J. Fluorine Chem., 2012, 144, 7-9.
[1].S. Singh, S. Chhina, V.K. Sharma, S.S. Sachev, J. Chem Soc.
[21].R. Rezaei, R. Khalifeh, M. Rajabzadeh, L. Dorosty, M.M.
Chem. Commun., 1982,
8, 453-454.
Doroodmand, Heterocycl. Commun., 2013, 19, 57–63.
[2].S. Tu, C. Miao, Y. Gao, F. Fang, Q. Zhuang, Y. Feng, D. Shia,
[22].K. Venkatesan, S.S. Pujari, K.V. Srinivasan, Synth. Commun.,
2009, 39, 228-241.
Synlett, 2004, 2, 255 -258.
[3].S.J. Tu, Z. Lu, D. Shi, C. Yao, Y. Gao, C. Guo, Synth.
Commun., 2002, 32, 2181-2185.
[23].G.M. Ziarani, A. Badiei, M. Hassanzadeh, S. Mousavi, Arab.
J. of Chem., 2014, 7, 335-339.
[4].M. Kaya, Y. Yıldırır, L. Türker, J. Heterocyclic Chem., 2009,
46, 294–297.
[24].V. B. Ashok, U. K. Bhagwat, G.G. Anil, Res. Chem Intermed,
2015, 41, 1447-1458.
[5].L. Ngadi, A.M. Galy, J.P. Galy, J. Barbe, A. Cremieux, D.
[25].R. Ezzat, E. Sara, K. Maryam, Chinese Journal of Catalysis,
2013, 34, 1513–1518.
Sharples, Eur. J. Med. Chem., 1990, 25, 67-70.
[6].M.J Wainwright, Antimicrob. Chemother., 2001, 47, 1-13.
[26].A. G. Mohammad, S. G. Javad, M. Halimeh, C. R. Chimie,
2012, 15, 969–974.
[7].K. Palani, D. Thirumalai, P. Ambalavanan, M.N.
Ponnuswamy, V.T. Ramakrishnan, J. Chem. Crystallogr.,
2005, 35, 751-760.
[27].D. Binoyargha, N. Sibaji, K.P. Amarta, Tetrahedron Letters,
2014, 55, 5236–5240.
[8].A. Srivastava, Nizamuddin, Indian J. Heterocycl. Chem.,
2004, 13, 261-264
[28].K. Amir, R. Mohammad, E. Hossein, M. Farid, B. Mehdi,
Chinese Journal of Catalysis, 2014, 35, 376–382
[9].Y. Mikata, M. Yokoyama, K. Mogami, M. Kato, I. Okura, M.
Chikira, S. Yano, Inorg. Chim. Acta., 1998, 279, 51-57.
6 | J. Name., 2012, 00, 1-3
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Journal Name
ARTICLE
[29].D. Pamarida, D. Arghya, B. Asim, M. Chhanda, Green [50].Z.Q. Tang, Y. Chen, C.C. Liu, K.Y. Cai, S.J. Tu, J. Heterocyclic
Chem., 2014, 16, 1426-1435.
Chem., 2010, 47, 363-367.
[30].F. Sen, G. Gökağaç, J. Phys. Chem., 2007, 111, 5715-5720.
[51].O.I. El-Sabbagh, M.A. Shabaan, H.H. Kadry, E.S. Al-Din,
Arch. der Pharm., 2010, 9, 519-527.
[31]. P.T.A. Sumodjo, E.J. Silva, T. Rabochai, Electroanal. Chem.,
1989, 271, 305-317.
[52].L.L. Zhao, D. Teng, Acta Crystallogr. Sect., 2008, 64, 1772-
1773.
[32].S. Ertan, F. Sen, S. Sen, G. Gökağaç, J. Nanopart. Res., 2012,
14, 922-926.
[53].Y. Chen, W.J. Hao, Z.Q. Tang, B. Jiang, C.M. Li, Acta
Crystallogr. Sect., 2007, 63, 3934-3940.
[33].H. Klug, L. Alexander, Wiley, New York, 1954.
[54].M. Kidwai, D. Bhatnagar, Tetrahedron Letters, 2010, 50
,
[34].T.C. Deivaraj, W.X. Chen, J.Y. Lee, J. Mater. Chem., 2003,
13, 2555-2560.
2700-2703.
[35].J. Zhao, P. Wang, W. Chen, R. Liu, X. Li, Q. Nie, J. Power
Sources, 2005, 160, 563–569.
[36].Y.T. Kim, T. Mitani, J. Catal., 2006, 238, 394-401.
[37].S. Ertan, F. Sen, G. Gökağaç, S. Sen, J Nanopart Res, 2013,
15, 1979-1985.
[38].F. Sen, G. Gökağaç, J Phys Chem C, 2007, 11, 1467-1473.
[39].S. Sen, F. Sen, G. Gökağaç, Phys Chem Chem Phys, 2011,
13, 6784-6792.
[40].F. Sen, S. Sen, G. Gökağaç, Phys Chem Chem Phys, 2011, 13
,
1676-1684.
[41].F. Sen, G. Gökağaç, J Appl Electrochem, 2014, 44, 199-207.
[42].Y. Li, W. Gao, L. Ci, C. Wang, P.M. Ajayan, Carbon, 2010, 48
,
1124–1130
[43].E. Yoo, T. Okata, T. Akita, K. Kohyama, J. Nakamura, I.
Honma, Nano Lett., 2009, , 2255-2259.
9
[44].C. Xu, X. Wang, J. Zhu, J. Phys. Chem. C., 2008, 112, 19.841-
19.845.
[45].R. Kou, Y. Shao, D. Wang, M.H. Engelhard, J.H. Kwak, J.
Wang, V.V. Viswanathan, C. Wang, Y. Lin, Y. Wang, I.A. Aksay,
J. Liu, Electrochem. Commun., 2009, 11, 954-957.
[46].S. Hrapovic, Y. Liu, K.B. Erkek, Anal. Chem., 2004, 76, 1083-
1088.
[47].I. E.S. Osama, A.S. Mohamed, H.K. Hanan, S.A.D. Ehab,
Arch. Pharm. Chem. Life Sci., 2010, 9, 519–527.
[48].D. Shi, S. Ni, G. Dou, Youji Huaxue, 2009, 29, 5, 788-793.
[49].R. Rezaei, R. Khalifeh, M. Rajabzadeh, L. Dorosty, M.M.
Doroodmand, Heterocycl. Commun., 2013, 19, 57–63.
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DOI: 10.1039/C5RA06441D
Pt NPs@GO as Highly Efficient and Reusable Catalyst for One-Pot Synthesis of
Acridinedione Derivatives
Handan Pamuka†, Burak Adayb†, Fatih Sena*, Muharrem Kayaa*
a Biochemistry Department, Faculty of Arts and Science, Dumlupınar University, Evliya Çelebi
Campus 43100 Kütahya, Turkey.
b Chemistry Department, Faculty of Arts and Science, Dumlupınar University, Evliya Çelebi
Campus 43100 Kütahya, Turkey.
Corresponding author: fatih.sen@dpu.edu.tr
Tel: +90 274 265 20 31 -3702 Fax: +90 274 265 20 56
Pt NPs@GO has been used for the first time for synthesizing acridinedione from dimedone, aromatic
aldehydes and various amines as a catalyst.