Graphene oxide anchored with sulfonic acid-functionalized glycerin: production, characterization and catalytic performance for the synthesis of N,N′-alkylidene bisamides

Article abstract of DOI:10.1007/s11164-020-04197-6

Abstract: A novel nanosheet-structured material, namely graphene oxide anchored with sulfonic acid-functionalized glycerin (GO@Gl-SO₃H), was prepared and characterized by FTIR, EDS, FESEM, TEM and XRD analyses. Afterward, its catalytic performa

Full text of DOI:10.1007/s11164-020-04197-6

Research on Chemical Intermediates
https://doi.org/10.1007/s11164-020-04197-6
Graphene oxide anchored with sulfonic acid‑functionalized
glycerin: production, characterization and catalytic
performance for the synthesis of N,N′‑alkylidene bisamides
Seham Naeim‑Fallahiyeh, et al. [full author details at the end of the article]
Received: 25 March 2020 / Accepted: 16 June 2020
© Springer Nature B.V. 2020
Abstract
A novel nanosheet-structured material, namely graphene oxide anchored with sul-
fonic acid-functionalized glycerin (GO@Gl-SO3H), was prepared and characterized
by FTIR, EDS, FESEM, TEM and XRD analyses. Afterward, its catalytic perfor-
mance was examined for the synthesis of N,N′-alkylidene bisamides through the
reaction of benzamide (2 eq.) and arylaldehydes (1 eq.) under solvent-free condi-
tions. GO@Gl-SO3H was a highly efective catalyst for the reaction and aforded the
products in high yields and short reaction times.
Graphic abstract
Solvent-free, 110°C
O
Ar
H
O
Ar
O
N
H
N
H
+
The reaction times:10-25 min
Yields:88-96%
H2N
O
O
NH2
The nanosheet-structured catalyst:graphene oxide anchored with sulfonic acid-functionalized glycerin
Keywords Graphene oxide anchored with sulfonic acid-functionalized glycerin
(GO@Gl-SO3h) · Nanosheet-structured material · N,N′-alkylidene bisamide ·
Solvent-free
Electronic supplementary material The online version of this article (https://doi.org/10.1007/s1116
4-020-04197-6) contains supplementary material, which is available to authorized users.
Vol.:(0123456789)
1 3

S. Naeim-Fallahiyeh et al.
Introduction
Graphene oxide (GO) is formed from fat sheets wherein carbon atoms with sp2
and sp3 hybridization are packed into a honeycomb lattice. In these sheets, car-
boxylic acid and hydroxyl groups have located at the edges, and epoxide and
hydroxyl groups have located on the basal surface. Because of existing carboxylic
acid and hydroxyl groups on the GO sheets, it can be easily functionalized by
organic and inorganic moieties to produce a wide range of GO derivatives. Due to
its unique properties such as proper thermal and chemical stability, high adsorp-
tion capability, high thermal conductivity, high carrier mobility, high structural
strength, high hydrophilic nature, appropriate mechanical property, good catalytic
activity, easy separation and aptitude to functionalize for diferent uses, many
research groups have been focused on production and application of functional-
ized graphene oxides in diferent scientifc, pharmaceutical and industrial felds
[1–23]. Some applications of functionalized GO and graphene derivatives include
SERS sensing and imaging [1], removal of heavy metal ions from water [2],
nanofltration [3], high-performance faradaic energy storage [4], wireless humid-
ity sensing [5] and biofunctionalization of protein in anticancer therapy [6], and
utilization as supercapacitor [7–9], anticorrosive agent [10], antifouling [11],
sorbents for enrichment of estrogens [12], drug carrier [13, 14] and catalysts in
organic transformation [15–23].
Solvent-free condition has several advantages relative to solution condition in
chemical reactions, including (1) consuming fewer energy, (2) afording aimed
product in shorter reaction time, and in higher yield and selectivity (often), (3)
possessing safer reaction medium, (4) easier workup and purifcation of product,
(5) preventing or decreasing by-products/waste formation and (6) being more
economic [24–27].
Amide and bisamide functional groups are present in the structure of numer-
ous biological, medical and industrial compounds [28–39]. Bisamides have been
utilized in the production of peptidomimetic materials [28]. Furthermore, they
have been applied as fundamental fragments to introduce gem-diaminoalkyl moi-
eties in retro-inverse pseudo-peptide compounds [29], and as ligands in the Ull-
mann reaction to produce potentially bioactive materials [30]. Bisamides have
been also used as antimicrobial [31], anti-infammatory [31], antitumor [32]
and drug release [33] agents. Bisamides coordinated with metal ions have been
utilized for removal of organic dyes [34], MRI blood-pool contrasting [35] and
bimodal imaging (optical/magnetic resonance) [36]; they have been also used as
inhibitor against α-glucosidase [37] and as reagents in organic synthesis [38, 39].
N,N′-Alkylidene bisamides, as a class of bisamide derivatives, could be prepared
by the reaction of primary amides (2 eq.) with aldehydes (1 eq.) in the presence
of a catalyst [40–48].
Considering the above-mentioned themes, it is highly desirable to introduce
a novel efective GO-based catalyst for the solvent-free preparation of N,N′-
alkylidene bisamides; in this work, we have done this. Herein, we have synthe-
sized graphene oxide anchored with sulfonic acid-functionalized glycerin (GO@
1 3

Graphene oxide anchored with sulfonic acid-functionalized…
Gl-SO3H) as a novel nanosheet-structured material and characterized it by FTIR,
EDS (energy-dispersive X-ray spectroscopy), FESEM (feld emission scanning
electron microscopy), TEM (transmission electron microscopy) and XRD (X-ray
difraction) analyses. Then, we have applied GO@Gl-SO3H as an efcacious cat-
alyst for the synthesis of N,N′-alkylidene bisamides by the reaction of benzamide
(2 eq.) and arylaldehydes (1 eq.) under solvent-free conditions.
Experimental
Chemicals and instruments
The utilized starting materials and solvents were bought from Merck or Fluka Chemi-
cal Companies. Thin-layer chromatography (TLC) using silica gel SIL G/UV 254
plates was used for the observation of the reactions progress. Measurement of melt-
ing points was done by a Buchi B-545 apparatus in open capillary tubes. FTIR spectra
were recorded using a Shimadzu IR-60 apparatus. A Bruker Avance DPX FT-NMR
spectrometer was used for running 1H and 13C NMR spectra. EDS was performed by
SAMx-EDS (France system) instrument. A FESEM device, model MIRA3TESCAN-
XMU, and a TEM apparatus, model Zeiss EM900, 80 keV were applied for the char-
acterization of morphologies, thickness and surface of the GO sheets. XRD analysis
was done by Cu Kα radiation (λ=1.5408, model: X’Pert PRO MPD, PANalytical, the
Netherlands).
Production of graphene oxide anchored with sulfonic acid‑functionalized glycerin
(GO@Gl‑SO3H)
Graphene oxide (GO) was prepared by oxidization of graphite via a modifed Hum-
mers’ method [49, 50]. GO (1.00 g) was added to a mixture of THF (20 ml) and dime-
thyl acetamide (DMA) (10 ml) and sonicated for 30 min at room temperature to give a
homogeneous emulsion. N,N’-Dicyclohexylcarbodiimide (DCC) (5 mmol, 1.03 g) and
triethylamine (6 mmol, 0.84 ml) were added to the emulsion and stirred for 3 h at room
temperature, and then glycerin (0.5 ml) was added, and stirring at room temperature
was continued for 48 h, and then it was centrifuged. The obtained precipitate was sepa-
rated by decanting, washed repeatedly with hot DMSO, deionized water and ethanol
and dried under vacuum at 80 °C to provide GO@Gl (Scheme 1). The produced GO@
Gl (1.00 g) was added to dried chloroform (20 ml) and sonicated at room tempera-
ture for 30 min; then, chlorosulfonic acid (8 mmol, 0.53 ml) was added gradually to
it and stirred for 24 h at room temperature. After centrifuging and washing the result-
ing precipitate by dry chloroform (3×10 ml), and drying, GO@Gl-SO3H was obtained
(Scheme 1).
1 3

S. Naeim-Fallahiyeh et al.
HO
OH
O
OH
HO
O
OH
OH
O
DCC, NEt3
THF/DMA
HO
HO
OH
O
HO
+
OH
HO
O
O
OH
(GO)
OH
HO
HO
O
O
OH
OH
OH
O
O
CHCl3
HO
O
O
ClSO3H
HO
+
HO
O
OH
HO
O
HO
O
O
O
HO
OH
HO
(GO@Gl)
OH
O
HO3S
HO
O
O
OH
SO3H
OH
O
O
O
O
HO
HO3S
O
HO
HO
O
OH
O
O
O
O
HO3S
O
O
O
SO3H
SO3H
O
HO
(GO@Gl-SO3H)
Scheme 1 Preparation of GO@Gl-SO3H
General procedure for the synthesis of N,N′‑alkylidene bisamides
A mixture of benzamide (2 mmol, 0.242 g), aldehyde (1 mmol) and GO@Gl-SO3H
(0.04 g) was powerfully stirred by a small rod at 110 °C. After consuming the reac-
tants (as observed by TLC), the mixture was cooled to room temperature, EtOAc (15
ml) was added and then it was stirred accompanied with refuxing for 2 min. The
1 3

Graphene oxide anchored with sulfonic acid-functionalized…
resulting mixture was centrifuged and decanted to isolate the unsolvable catalyst.
The obtained EtOAc after the decanting was evaporated, and the precipitate (crude
product) was purifed by recrystallization from EtOH/H2O (95/5).
Note: Selected spectral data and original spectrums of the prepared bisamides are
presented in supplementary material.
Results and discussion
Characterization of the catalyst
The novel nanosheet-structured catalyst, namely graphene oxide anchored with sul-
fonic acid-functionalized glycerin (GO@Gl-SO3H), was characterized by FTIR,
EDS, FESEM, TEM and XRD analyses.
The FTIR spectrums of GO@Gl and GO@Gl-SO3H (Scheme 1) are illustrated
in Fig. 1, and the obtained data from the spectrum of GO@Gl-SO3H are reported
in Table 1. As Table 1 shows, the peaks related to all expected functional groups
Fig. 1 FTIR spectrums of GO@Gl and GO@Gl-SO3H
1 3

S. Naeim-Fallahiyeh et al.
Table 1 FTIR data of GO@Gl-SO3H
Peak (cm−1
)
Functional group or bond
587
SO2 (bending)
1055
1162
~1233
1576
1627
C–O (stretching vibration)
SO2 (symmetric stretching)
SO2 (asymmetric stretching)
C=C (stretching vibration)
C=O of GO (stretching vibration)
~1718
2852
2928
C=O of ester group (stretching vibration)
sp3 C–H of glycerol chain (symmetric stretching vibration)
sp3 C–H of glycerol chain (asymmetric stretching vibration)
sp2 C–H (stretching vibration)
~3040
3000–3730
OH group of the SO3H, and OH groups of GO (stretching)
and bonds in the structure of GO@Gl-SO3H were seen in its spectrum; inter-
pretation of the FTIR data is in agreement with those reported for the similar
functional groups and bonds [19, 23, 42]. In another study, to confrm successful
anchoring of SO3H with the GO-based material, the FTIR data of GO@Gl-SO3H
were compared with those of GO and GO@Gl (the FTIR spectrum of GO have
been reported in the literature [51–53]). The peaks related to the same bonds and
functional groups in GO, GO@Gl and GO@Gl-SO3H were observed in the three
spectrums (i.e., C–O, C=C, C=O, sp3 C–H of glycerol chain, sp2 C–H and OH
groups of GO). However, the peaks corresponding to SO3H were seen only in
the spectrum of GO@Gl-SO3H (i.e., 587, 1162, 1233 and 3000–3730 cm−1); this
Fig. 2 The EDS spectrum of GO@Gl-SO3H
1 3

Graphene oxide anchored with sulfonic acid-functionalized…
Fig. 3 FESEM micrographs of the GO-based material
subject confrmed successful functionalization of GO@Gl with SO3H group, and
formation of GO@Gl-SO3H.
In the structure of graphene oxide anchored with sulfonic acid-functionalized
glycerin, there are carbon, oxygen and sulfur; this theme was obviously observed in
the EDS spectrum (Fig. 2).
The FESEM micrographs of GO@Gl-SO3H are indicated in Fig. 3; the micro-
graphs displayed homogeneous nanosheets with crumpled structure in one edge.
The TEM micrographs of the nanosheets surface are shown in Fig. 4; according to
the micrographs, the nanosheets surface was smooth with a slight fracture.
The XRD diagrams of GO, GO@Gl and GO@Gl-SO3H are shown in Fig. 5.
In the GO diagram, a sharp peak was observed at 2θ ≈ 9.6°, which is related to
the crystalline nature of the pristine graphene oxide; this characteristic peak was
seen at 2θ ≈ 9.3° for GO@Gl and GO@Gl-SO3H. By anchoring graphene oxide
with glycerol and sulfonic acid-functionalized glycerol, the peak intensity (at 2θ
Fig. 4 TEM micrographs of GO@Gl-SO3H
1 3

S. Naeim-Fallahiyeh et al.
Fig. 5 The XRD diagrams of GO (a), GO@Gl (b) and GO@Gl-SO3H (c)
≈ 9.3°) was decreased, and some peaks (with low intensity) appeared at 2θ ≈
16.0°–40.0° (for GO@Gl: 2θ ≈ 16.9°, 18.8°, 21.5°, 23.4°, 24.8°, 27.9°, 30.1°,
32.9°, 34.6°, 39.5°, and for GO@Gl-SO3H: 2θ ≈ 16.9°, 18.8°, 21.5°, 23.4°, 24.8°,
26.9°, 27.9°, 30.2°, 32.8°, 39.5°). Comparing the data of GO diagram with the
two other spectrums revealed that by anchoring the mentioned groups with GO,
some amount of its crystalline form is converted into amorphous state. Further-
more, most of the data obtained from the XRD patterns of GO@Gl and GO@
Gl-SO3H were similar; this topic can be attributed to unchanging the GO@Gl
scafold after functionalization by SO3H, i.e., almost all the SO3H groups have
bonded with the hydroxyl groups of glycerin. The literature data verifed these
explanations [20].
NO2
O2N
CHO
O
O
GO@Gl-SO3H
+
Solvent-free,Different conditions
N
H
N
H
H2N
O
O
NH2
Scheme 2 The model reaction
1 3

Graphene oxide anchored with sulfonic acid-functionalized…
Examining catalytic performance of GO@Gl‑SO3H for the synthesis
of N,N′‑alkylidene bisamides
To attain most appropriate reaction conditions for the production of N,N′-alkylidene
bisamides, at frst, the condensation of benzamide (2 mmol) with 4-nitrobenzalde-
hyde (1 mmol) was chosen as a model reaction (Scheme 2), and infuence of the
catalyst amount and temperature on it was studied under solvent-free conditions. For
this purpose, the reaction was checked in the presence of diferent catalytic amounts
of GO@Gl-SO3H (0.02–0.05 g) at a range of 90–115 °C. According to the obtained
reaction times and yields, the most appropriate amount of the catalyst and the reac-
tion temperature were 0.04 g and 110 °C, respectively (time 10 min; yield 96%).
After obtaining the most appropriate conditions for the reaction, efcacy and
generality of GO@Gl-SO3H were assessed by reaction of benzamide with diverse
arylaldehydes, consisting of benzaldehyde and aromatic aldehydes bearing halogen,
electron-attracting and electron-donating substituents; the resulting reaction times
and yields are illustrated in Table 2. As it can be seen in Table 2, aldehydes pos-
sessing bromo, chloro, nitro, methyl and methoxy substituents on ortho-, meta- and
para-positions aforded the corresponding N,N′-alkylidene bisamides in short times
and high yields. Thus, graphene oxide anchored with sulfonic acid-functionalized
glycerin was a highly efcacious and general catalyst for the reaction.
Table 2 Solvent-free synthesis of N,N′-alkylidene bisamides using GO@Gl-SO3H
O
Ar
H
O
Ar
O
GO@Gl-SO3H
Solvent-free,110°C
N
H
N
H
+
H2N
O
O
NH2
Product
Ar
Time (min)
Yielda (%)
M.p., °C found (reported)
1a
1b
1c
1d
1e
1f
C6H5
15
15
15
15
10
15
10
10
15
25
91
93
90
89
96
92
95
96
90
88
215–217 (216–218) [42]
231–233 (226–228) [47]
252–254 (254–256) [48]
194–196 (192–193) [43]
251–253 (252–254) [47]
254–256 (257–259) [40]
232–234 (230–232) [43]
261–263 (263–264) [41]
242–244 (241–244) [44]
225–227 (223–225) [42]
3-BrC6H4
4-BrC6H4
2,4-Cl2C6H3
4-ClC6H4
2-O2NC6H4
3-O2NC6H4
4-O2NC6H4
4-CH3C6H4
4-CH3OC6H4
1g
1h
1i
1j
aIsolated yield
1 3

S. Naeim-Fallahiyeh et al.
O
H
O
O
Ar
O
Ar
H2N
Step1
Ph
O
GO@Gl-SO3H
GO@Gl-SO3H
H
Ar
Ar
Ph
O
N
H
OH
Ph
N
H
O
H
O
H
H
O
O
S
O
O
S
O
O
S
O
O
O
H
O
Ar
O
O
H2N
Ph
GO@Gl-SO3H
_
H2O
Step3
Ph
N
Ar
Ph
N
N
Ph
Ph
N
Ar
H
H
Step2
(The product)
Scheme 3 The proposed mechanism
Table 3 Comparing the reaction conditions and the results of GO@Gl-SO3H with those of some
reported catalysts for the preparation of products 1a, 1e and 1j
Catalyst
Conditions
Time (min) for
Yield (%)
References
products 1a/1e/1j for products
1a/1e/1j
GO@Gl-SO3H
Montmorillonite K10
Boric acid
Solvent-free, 110 °C 15/10/25
Solvent-free, 100 °C 80/–a/180
Toluene, 120 °C
91/96/88
85/–a/72
92/65/–a
85/60/–a
This work
[40]
[41]
960/2880/–a
20/30/–a
Boric acid
CH2Cl2, microwave
[41]
irradiation (650 W)
Nano-[DSPECDA][HSO4]b
ZnO/KIT-6@NiFe2O4
Solvent-free, 90 °C
Solvent-free, 60 °C
Toluene, refux
30/–a /30
10/10/10
30/25/50
91/–a /83
90/94/85
85/83/80
[42]
[43]
[44]
3D-network polymer
-supported ionic liquid
KH2PO4 supported on silica Solvent-free, 80 °C
Catalyst-free
14[NaP5W29MoO110
NiFe2O4@SiO2-PPA
15/15/15
87/90/81
85/80/85
86/82/–a
86/86/–a
[45]
[46]
[47]
[48]
Solvent-free, 100 °C 5/10/30
H
]
CH3OH, refux
CH3OH, refux
90/70/–a
80/60/–a
aIn the work, this product has not been prepared
bNano-2-[N’,N’-dimethyl-N’-(silica-n-propyl)ethanaminium chloride]-N,N-dimethylaminium bisulfate
Based on the literature [42, 45], a plausible mechanism was proposed for the syn-
thesis of N,N′-alkylidene bisamides (Scheme 3). GO@Gl-SO3H has catalyzed the
reaction by its acidic group (SO3H); the catalyst tasks are clearly illustrated in the
mechanism, which include (1) activation of the carbonyl groups in steps 1 and 3, to
accept nucleophilic attack of benzamide nitrogen, and (2) activation of the hydroxyl
group in step 2 for removal of a H2O molecule.
In another study, the reaction conditions and the results of GO@Gl-SO3H for the
preparation of compounds 1a, 1e and 1j were compared with those of some reported
catalysts (Table 3). As Table 3 indicates, GO@Gl-SO3H aforded the products in
1 3

Graphene oxide anchored with sulfonic acid-functionalized…
higher yields in comparison with the other catalysts. The reaction times of GO@
Gl-SO3H are also shorter than most of the other catalysts. Moreover, the reaction
medium of our protocol (solvent-free conditions) is better than the reaction medium
of the protocols in which toxic organic solvents have been used.
Conclusions
In conclusion, a novel nanosheet-structured catalyst (GO@Gl-SO3H) was intro-
duced for organic synthesis. In this work, it could catalyze a valuable organic trans-
formation, i.e., the synthesis of N,N′-alkylidene bisamides. Several advantages are
associated with this catalytic process, such as efcacy, generality, short reaction
times, high yields, easy separation of the catalyst from the reaction medium, simple
purifcation of the products (by recrystallization) and performing the reactions under
solvent-free conditions.
Acknowledgements The support of this work by Research Council of Payame Noor University is grate-
fully acknowledged. Moreover, we appreciate Abdolkarim Zare (Payame Noor University) for helping us
to do this research.
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Graphene oxide anchored with sulfonic acid-functionalized…
Afliations
Seham Naeim‑Fallahiyeh1 · Esmael Rostami1 · Habibeh Golchaman1 ·
Soheila Kaman‑Torki1
*
Esmael Rostami
esmaelrostami@gmail.com; e.rostami@pnu.ac.ir
1
Department of Chemistry, Payame Noor University, PO Box 19395-3697, Tehran, Iran
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