Adsorption of rhodamine B by organic porous materials rich in nitrogen, oxygen, and sulfur heteroatoms

Article abstract of DOI:10.1039/d0nj05750a

Rhodamine B is a non-degradable carcinogenic dye, so it is of great significance to remove rhodamine B from wastewater. We designed and prepared a novel porous organic polymer adsorbent (DAPS-TP-POP), which contains abundant N, O, and S heteroatoms. DAPS-TP-POP was characterized through FT-IR, PXRD, TGA, TEM, BET etc. The results show that DAPS-TP-POP has high stability and abundant heteroatoms. DAPS-TP-POP has good adsorption capacity for rhodamine B. Besides, it also shows excellent recyclability.

Full text of DOI:10.1039/d0nj05750a

NJC
View Article Online
View Journal | View Issue
PAPER
Adsorption of rhodamine B by organic porous
materials rich in nitrogen, oxygen, and sulfur
heteroatoms†
Cite this: New J. Chem., 2021,
45, 3448
Xiao-Cheng Du, Ji-Hua Zhu, Zheng-Jun Quan * and Xi-Cun Wang
*
Rhodamine B is a non-degradable carcinogenic dye, so it is of great significance to remove rhodamine
B from wastewater. We designed and prepared a novel porous organic polymer adsorbent (DAPS-TP-
POP), which contains abundant N, O, and S heteroatoms. DAPS-TP-POP was characterized through
FT-IR, PXRD, TGA, TEM, BET etc. The results show that DAPS-TP-POP has high stability and abundant
heteroatoms. DAPS-TP-POP has good adsorption capacity for rhodamine B. Besides, it also shows
excellent recyclability.
Received 25th November 2020,
Accepted 14th January 2021
DOI: 10.1039/d0nj05750a
rsc.li/njc
design of a highly efficient adsorbent which is environmentally
friendly, easy to operate, and recyclable is of great significance.
1
. Introduction
Organic dyes are widely used in various industries, such as Porous organic polymers (POPs) are a class of materials that have
textiles, leather, plastics, paper, cosmetics, medicine, printing, attracted much attention for their light weight, porosity, high
1
,2
etc. However, many organic dyes are toxic, carcinogenic, and chemical/thermal stability, large specific surface area, and easy
2
1,22
non-degradable, which has caused a series of environmental recyclability.
Porous organic polymers mainly include hyper-
problems. In particular, the water pollution problem caused cross-linked polymers (HCPs), polymers of intrinsic microporosity
by the large-scale use of dyes has attracted widespread atten- (PIMs), conjugated microporous polymers (CMPs), and covalent
23
tion, because it has led to the death of a large number of organic frameworks (COFs). Compared with traditional carbon-
marine organisms and has seriously threatened the safety of based materials, organic porous polymers have certain advantages
3
–8
24,25
human drinking water.
For example, rhodamine B is a in terms of modifiability and recyclability.
The meticulous
synthetic basic dye which is often used as a dye in industrial design of the building blocks can accurately control the shape and
production. Long-term use of water containing rhodamine B size of the voids of POPs, which brings convenience to the design
9
,10
26–34
by humans or animals may cause cancer or death.
Hence, of efficient adsorbents.
Recent studies have shown that the
how to remove dyes from water has been an urgent problem to introduction of heteroatoms such as N, O and S into the porous
1
1,12
be solved.
polymer network can significantly improve the adsorption capa-
The possible reason is that heteroatoms
have a significant regulating effect on the surface charge of the
35–39
The current methods for removing dyes from wastewater city of the adsorbent.
mainly include chemical, physical and biological methods.
1
3,14
Among these, the adsorption method is easy to operate and material, thereby promoting the interaction between the host
environmentally friendly. Thus, it is considered to be one of the molecule and the guest molecule, which makes the polymer
1
5–18
26,27
most effective methods to remove dyes.
Subsequently, a material have a stronger ability to adsorb dye molecules.
large number of adsorbents have been developed, mainly Therefore, the introduction of heteroatoms into the polymer
including polymer materials, supramolecular gels, metal– network is of great significance.
organic frameworks, graphene, activated carbon, metal oxides,
In this study, we chose 2,4,6-trihydroxybenzene-1,3,5-
1
9,20
0
carbon nanotubes etc.
However, many adsorbents have tricarbaldehyde (TP) and 4,4 -diaminodiphenyl disulfide (DAPS)
disadvantages of low adsorption efficiency and poor recyclability, as the building blocks and successfully synthesized organic
which limit their potential application range. Therefore, the porous material DAPS-TP-POP. DAPS-TP-POP exhibits high
stability in water and various organic solvents. Subsequently,
International Scientific and Technological Cooperation Base of Water Retention
the adsorption performance of DAPS-TP-POP for dyes has been
studied. It has good adsorption capacity for rhodamine B under
Chemical Functional Materials, College of Chemistry and Chemical Engineering,
Northwest Normal University, Lanzhou, Gansu 730070, P. R. China.
alkaline conditions, and the adsorption capacity reached
E-mail: wangxicun@nwnu.edu.cn, quanzhengjun@hotmail.com
ꢀ
1
5
9.2 mg g . After 5 cycles, about 90% of the removal capacity
†
Electronic supplementary information (ESI) available. See DOI: 10.1039/
d0nj05750a
was still retained.
3448 | New J. Chem., 2021, 45, 3448ꢀ3453
This journal is The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2021

View Article Online
Paper
NJC
2. Experimental
3. Results and discussion
2.1 Materials and methods
3.1. Characterization of DAPS-TP-POP
All reagents are analytically pure and can be used directly
3.1.1 Fourier transform infrared spectroscopy characteri-
without purification. 2,4,6-Trihydroxybenzene-1,3,5-tricarbaldehyde zation. The FT-TR of DAPS-TP-POP showed that the stretching
4
0
ꢀ1
(
TP) was synthesized by the method already reported; the peak of –NH
2
(3100–3300 cm , corresponding to free diamine)
ꢀ
1
synthetic method is shown in Scheme S1 (ESI†). The synthetic disappeared. The stretching peaks of –CQC (1568 cm ) and
method of 4,4 -diaminodiphenyl disulfide (DAPS) is shown in –C–N (1249 cm ) appeared, and the carbonyl stretching peak
Scheme S2 (ESI†). H NMR and C NMR spectra were recorded shifted from 1643 cm (corresponding to carbonyl aldehyde)
with an Agilent 600 MHz spectrometer. FT-IR spectra were to 1613 cm ; all information shows the successful synthesis of
recorded from 400 to 4000 cm by using KBr pellets on a DAPS-TP-POP (Fig. 1a).
DIGILAB FTS-3000 spectrometer. Powder X-ray diffraction 3.1.2 Thermal stability. The thermogravimetric analysis
PXRD) patterns were taken on a D/max 2200PC diffractometer curve of DAPS-TP-POP is shown in Fig. 1b. There is a slight
0
ꢀ1
1
13
ꢀ1
ꢀ
1
ꢀ
1
(
at room temperature. Morphology analysis was performed loss of quality at about 200 1C, which may be caused by the
using an ULTRA Plus scanning electron microscope (SEM). Ther- evaporation of residual solvent on the surface of the material.
mogravimetric analysis (TGA) was performed on a NETZSCH At about 380 1C, there is a large loss of quality, indicating that
Instruments thermal analyzer (STA449C) from 25 to 800 1C at the structure is beginning to collapse. However, the quality can
ꢀ
1
a heating rate of 10 1C min under an N2 atmosphere. N2 still be maintained within 60% before 500 1C. Therefore, TGA
adsorption–desorption isotherms were measured on an Autosorb shows that DAPS-TP-POP has higher thermal stability and can
iQ Station (QuantaChrome Instruments V 5.0) at 77 K; the be used in practical applications at higher temperatures.
Brunauer–Emmett–Teller (BET) method was utilized to calculate
3.1.3 Surface area measurement. The surface area and
the specific surface areas and pore volume. The UV-vis absorp- porosity of DAPS-TP-POP were measured by nitrogen adsorp-
tion spectra were recorded on an Agilent 8453 UV-vis tion–desorption analysis at 77 K; the results are shown in Fig. 2.
spectrophotometer.
We use the Brunauer–Emmett–Teller (BET) model to calculate
2
ꢀ1
the surface area of DAPS-TP-POP as 4.279 m g , and the total
3
ꢀ1
pore volume was calculated as 0.038 cm g (P/P = 0.995). The
0
2.2 Synthesis of DAPS-TP-POP
pore size distribution diagram is shown in Fig. 2b; the location
2
3
5
,4,6-Trihydroxybenzene-1,3,5-tricarbaldehyde (0.15 mmol, of the maximum distribution peak is at 3.3 nm, the pore width
1.5 mg) and 4,4 -diaminodiphenyl disulfide (0.225 mmol, is mainly distributed between 3 and 25 nm, and the molecular
5.9 mg) in a Pyrex tube (10 mL) were dissolved in a mixed diameter of rhodamine B is 1.44 nm (Fig. S12, ESI†), which
0
solvent of dioxane and trimethylbenzene (V : V 1 : 1 mL) with allows rhodamine B to enter the pores and increases the
.2 mL of 6 M aqueous acetic acid using a solvothermal adsorption sites, so it is beneficial for the adsorption process.
process. This mixture was sonicated for 15 min at room
3.1.4 Powder X-ray diffraction (PXRD) analysis. The crystal-
0
temperature and degassed by three freeze–pump–thaw cycles linity of DAPS-TP-POP was characterized by powder X-ray
at ꢀ85 1C. Then the tube was sealed under vacuum conditions diffraction. As shown in Fig. S6 (ESI†), the observed PXRD
and heated at 120 1C for 3 days. After, the collected pattern of DAPS-TP-POP exhibited a broad peak at 10–401,
yellow powder was washed with DMSO, DMF, THF, and indicating that it was an amorphous polymer with low crystal-
acetone several times. Then the yellow powder was dried at linity. The reason for the poor crystallinity may be the existence
1
00 1C under vacuum conditions for 12 hours to obtain DAPS- of flexible building blocks.
TP-POP in an isolated yield of 64.2 mg (75.8%) (Scheme 1).
3.1.5 Scanning electron microscopy (SEM) study. SEM
Anal. calcd for (C27 : C, 61.35%; N, 7.95%; S, images of DAPS-TP-POP are shown in Fig. 3a and b. DAPS-TP-
8.19%; O, 9.08%. Results: C, 60.32%; N, 7.86%; S, 18.25%; POP exhibits a spherical stacking morphology. The elemental
18 3 3 3 n
H N O S )
1
O, 11.13%.
mapping images of carbon, oxygen, nitrogen, and sulfur of the
Fig. 1 (a) FTIR spectra of DAPS-TP-POP, TP and DAPS; and (b) TGA of
DAPS-TP-POP measured from room temperature to 800 1C under an air
ꢀ1
Scheme 1 Schematic representation of the synthesis of DAPS-TP-POP.
atmosphere with a heating rate of 10 1C min .
This journal is The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2021
New J. Chem., 2021, 45, 3448ꢀ3453 | 3449

View Article Online
NJC
Paper
shown in Fig. S5 (ESI†); the position and intensity of each
characteristic peak are the same, indicating that it can exist
stably in various solutions.
3.2 Dye adsorption
3.2.1 Standard curve. A standard solution of rhodamine B
was analyzed by using a single wavelength method; the results
show that its maximum absorption wavelength is 554 nm.
Subsequently, standard solutions with concentrations of 2, 4,
Fig. 2 Nitrogen absorption–desorption isotherms (a) and pore size distri-
bution plot (b) of DAPS-TP-POP.
ꢀ1
6, 8, 10, and 12 mg L were analyzed by using UV-vis spectro-
photometry to obtain a curve and fitting equation. The fitting
equation is used for subsequent dye solution concentration
determination (Fig. S10, ESI†).
3
.2.2 The influence of pH on the adsorption capacity.
ꢀ1
2
.0 mg DAPS-TP-POP was added to 7 ml of 20 mg L dye
solutions with pH values of 3, 6, 8, and 11, respectively (Fig. 4).
The solutions were stirred at 200 rpm for 24 h to achieve
adsorption equilibrium, and the adsorbent was removed by
centrifugation and standing. Then, the concentration of resi-
dual rhodamine B of the supernatant was measured. The result
is shown in Fig. 4; DAPS-TP-POP has good adsorption capacity
under acidic and basic conditions. However, it has a stronger
ꢀ
1
adsorption capacity with 35.1 mg g under alkaline conditions.
The zeta potential is shown in Fig. S8 (ESI†). As the pH
increases, the zeta potential becomes more negative, and the
electrostatic attraction between rhodamine B and DAPS-TP-POP
becomes stronger. Therefore, the higher the pH, the stronger
the adsorption capacity of DAPS-TP-POP for rhodamine B.
3.2.3 Adsorption kinetics. 2.0 mg of DAPS-TP-POP was
added to 7 mL of rhodamine B solution (pH = 11) with an initial
ꢀ1
concentration of 10 mg L . The solutions were stirred at 200 rpm
for 5, 10, 30, 60, 110, 150, 250, 310, 500, 600, and 800 min, and the
adsorbent was removed by centrifugation and standing. Then, the
concentration of residual rhodamine B of the supernatant was
measured. The adsorption amount of DAPS-TP-POP at time t is
analyzed by eqn (1) to obtain the kinetic curve for rhodamine B.
ðC0 ꢀ CeÞV
qt ¼
(1)
m
ꢀ1
ꢀ1
0 e
Fig. 3 SEM images of DAPS-TP-POP with a scale bar of 1 mm (a) and 200 nm Here, C (mg L ) and C (mg L ) are the initial and equilibrium
(
b), respectively. EDS mapping images of DAPS-TP-POP: (c) electron micro- concentration of the dye solution, V (L) is the volume of dye
scope image, and C (d), O (e), S (f), and N (g) element EDS mapping.
solution added, and m (g) is the mass of the adsorbent.
prepared material are shown in Fig. 3c–g, indicating that these
elements are evenly distributed. The EDX of DAPS-TP-POP is
shown in Fig. S7 (ESI†). The content and ratio of C, N, O, and S
are basically consistent with the elemental analysis.
3.1.6 Solvent stability. To expand the application range of
materials, the stability of materials in various solutions and
water must be considered. Therefore, we have conducted
stability tests in various solutions, including an aqueous
solution of HCl at pH = 1, an aqueous solution of NaOH at
pH = 13, DMF, THF, methanol and acetone (stirred for 24 h at
room temperature). The stability of DAPS-TP-POP was verified
by Fourier transform infrared spectroscopy. The results are Fig. 4 Effects of pH on the adsorption of rhodamine B.
3450 | New J. Chem., 2021, 45, 3448ꢀ3453
This journal is The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2021

View Article Online
Paper
NJC
Table 1 Kinetic parameters of rhodamine B adsorption on DAPS-TP-POP correlation coefficient is closer to 1 than the pseudo-first-
order kinetic correlation coefficient, and the saturated adsorp-
Models
Parameters
DAPS-TP-POP
tion amount calculated by the pseudo-second-order kinetics
ꢀ
1
Pseudo-first order
K
q
R
K
q
1
(min
)
0.0047
5.42
0.9324
0.0084
31.5
31.25
0.9994
ꢀ1
ꢀ1
ꢀ
1
(31.25 mg g ) is closer to the experimental value of 31.5 mg g .
c2 al (mg g
)
Therefore, the adsorption of rhodamine B conforms to the
pseudo-second-order kinetic model, indicating that chemi-
sorption is dominant in this adsorption process.
ꢀ
1
ꢀ1
Pseudo-second order
2
(g mg min )
1
ꢀ
exp (mg g
)
1
ꢀ
q
c2 al (mg g
)
3.2.4 Isothermal adsorption line. 2 mg DAPS-TP-POP was
R
added to 7 mL rhodamine B solutions (pH 11, adjusted) with
ꢀ
1
different initial concentrations (5–30 mg L ) at room tempera-
ture, and stirred at 200 rpm for 6 h. After adsorption equili-
brium, the adsorbent was removed by centrifugation and
standing. Then, the concentration of residual rhodamine B of
the supernatant was measured. The isotherm adsorption line of
rhodamine B was prepared by analyzing the relationship
To study the kinetic adsorption behavior of DAPS-TP-POP,
we used two common kinetic models of Lagergren pseudo-first-
order and pseudo-second-order.
The pseudo-first-order dynamics is defined as eqn (2).
ln(q
e
ꢀ q
t
) = ln q
e
ꢀ K
1
t
(2)
e
between the equilibrium adsorption amount (q ) of DAPS-TP-
The pseudo-second-order dynamics is defined as eqn (3).
POP and the equilibrium concentration (C ) of the solution.
e
For further studying the adsorption mechanism of DAPS-TP-
POP, two different adsorption isotherm models were used,
namely the Langmuir model and Freundlich model. Among
t
1
t
¼
þ
(3)
qt
K2qe2 qe
ꢀ
1
ꢀ1
e t
Here, q (mg g ) and q (mg g ) are the equilibrium adsorption them, the Langmuir model is the most widely used adsorption
amount and the adsorption amount at a certain time t, and K
1
isotherm model, assuming that adsorption occurs at a specific
(g mg min ) are the pseudo-first-order and uniform position within the adsorbent with monolayer adsorp-
pseudo-second-order adsorption rate constants, respectively. The tion, and each site can only accommodate one molecule or
ꢀ
1
ꢀ1
ꢀ1
(min ) and K
2
calculation results of other parameters are shown in Table 1.
The kinetic adsorption results are shown in Fig. 5. Fig. 5a
shows that the adsorption rate is fast within the first 30 minutes.
The main reason is that it is performing surface adsorption at
atom. The Langmuir isotherm model is represented by eqn 4
ce
qe
ce
1
¼
þ
(4)
qm KLqm
ꢀ1
ꢀ1
this stage. Interestingly, when the surface adsorption reaches where q (mg g ) and qm (mg g ) represent the equilibrium
e
saturation, the dye molecules will diffuse into the gap through adsorption amount and maximum adsorption amount of the dye
ꢀ
1
the material’s surface, but the diffusion into the gap has greater solution, respectively. C (mg L ) is the equilibrium concentration
e
ꢀ
1
resistance. So we will observe that the adsorption rate is very slow of the dye solution, and K (L g ) is the Langmuir adsorption
L
after 30 min, and finally reaches the adsorption equilibrium after constant.
310 minutes. We introduced pseudo-first-order kinetic (Fig. 5b)
The Freundlich equation is applied to the adsorption of non-
and pseudo-second-order kinetic (Fig. 5c) models to study ideal surfaces and multilayer adsorption. The Freundlich isotherm
the adsorption behavior of dyes. The parameters are shown in model is represented by eqn (5).
Table 1. It is found that the pseudo-second-order kinetic
1
ln qe ¼ ln ce þ ln KF
(5)
n
ꢀ
1
ꢀ1
Here, q
e
(mg g ) and C
e
(mg L ) are the adsorption amount and
ꢀ
1
F
concentration at equilibrium, K (L g ) is the Freundlich con-
stant, and n is the heterogeneity factor.
The results are shown in Fig. 6. The adsorption isotherm
(
Fig. 6a) shows that the maximum adsorption of rhodamine B
ꢀ
1
is 59.2 mg g . The Langmuir and Freundlich isotherms are
shown in Fig. 6b and c, respectively. Other parameters are
obtained by calculation as shown in Table 2. The data shows
that the correlation coefficient of the Langmuir model is closer
to 1, and the maximum adsorption amount calculated by the
ꢀ1
Langmuir model is 61.3 mg g , which is closer to the experi-
ꢀ1
mental value (59.2 mg g ). Therefore, the Langmuir model
better explained the adsorption process of rhodamine B than
the Freundlich model, indicating that the adsorption of rhoda-
mine B on DAPS-TP-POP belongs to monolayer adsorption.
3
.2.5 Cycleability test. To investigate the recoverability of
Fig. 5 (a) Effect of contact time on the adsorption of rhodamine B.
b) Pseudo first-order kinetics, and (c) pseudo second-order kinetics.
(
DAPS-TP-POP, we carried out adsorption and desorption
This journal is The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2021
New J. Chem., 2021, 45, 3448ꢀ3453 | 3451

View Article Online
NJC
Paper
Table 3 Comparison of the removal of rhodamine B dyes by different
adsorbents
ꢀ1
Entry
Adsorbent
Adsorption capacity (mg g
)
Ref.
1
2
3
4
5
6
TCGA-1
31.95
102.0
43.47
16.18
59.17
59.2
46
45
10
44
CS-CNT-H
Dowex 5WX8
MOF-5/COF
PWC
43
DAPS-TP-POP
This work
3.2.6 Adsorption mechanism. The adsorption capacity of
an adsorbent is influenced by many factors, such as the surface
structure and functional behavior of the adsorbent molecules,
1
6,41,42
and the characteristics of the adsorbent itself.
In this
study, rhodamine B can be easily adsorbed on the adsorbent
through van der Waals force and hydrogen bonding interac-
tions because the adsorbent itself is rich in nitrogen, oxygen,
and sulfur heteroatoms. By comparing the infrared spectra of
the materials before and after the dye adsorption, it is found
that the infrared characteristic peaks of the complex have
slightly shifted after the dye adsorption (Fig. S9, ESI†). The
Fig. 6 (a) Adsorption isotherms for the adsorption of rhodamine B at
2
98 K, and (b) Langmuir and (c) Freundlich isotherms for the adsorption of
rhodamine B.
ꢀ
1
Table 2 Isotherm parameters for rhodamine B adsorption on DAPS-TP-
POP at 298 K
characteristic peak of carbonyl has moved from 1610 cm to
ꢀ1
1
612 cm . The characteristic peak of the NH stretching vibra-
ꢀ1
tion broadened significantly and moved from 3450 cm to
Models
Parameters
DAPS-TP-POP
ꢀ
1
3
427 cm . The shift of the characteristic peak of the complex
ꢀ
1
Langmuir
q
m,cal (mg g
)
61.3
ꢀ1
may be due to the electrostatic attraction and hydrogen bond
interaction between the adsorbent and the dye molecule.
K
R
K
n
R
L
2
(L mg
)
0.8928
0.9936
31.68
4.69
ꢀ1
Freundlich
F
2
(mg L
)
0.9765
4. Conclusions
In summary, we have synthesized a new type of porous material
under solvothermal conditions. DAPS-TP-POP has abundant N,
S, and O heteroatoms, which makes it have good adsorption
capacity for rhodamine B. In addition, DAPS-TP-POP also
exhibits high stability and good recyclability. After 5 cycles, a
removal rate of about 90% can still be maintained. Compared
with other adsorbents that adsorb rhodamine B, DAPS-TP-POP
experiments. 5.0 mg DAPS-TP-POP was added to 18 mL of the dye
ꢀ
1
solution with an initial concentration of 10 mg L . After the
adsorption was completed, the adsorbent was removed by cen-
trifugation and standing. The concentration of residual rhoda-
mine B was measured by using UV-vis spectrophotometry.
Subsequently, DAPS-TP-POP after adsorption of the dye was
ultrasonically cleaned twice with methanol and acetone in
sequence and then dried for the next cycle test. The results are
shown in Fig. 7. After 5 cycles, about 90% removal rate can be
retained, indicating its excellent recyclability and sustainability.
9
,10,43–46
also shows good adsorption capacity (Table 3).
There-
fore, DAPS-TP-POP has broad application prospects in the field
of environmental restoration.
Conflicts of interest
There are no conflicts to declare.
Acknowledgements
This work was financially supported by the Key Talent Projects
of Gansu Province (2019–39).
Notes and references
1
B. N. Patra and D. Majhi, J. Phys. Chem. B, 2015, 119,
Fig. 7 Recyclability of DAPS-TP-POP for the adsorption of rhodamine B.
8154–8164.
3452 | New J. Chem., 2021, 45, 3448ꢀ3453
This journal is The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2021

View Article Online
Paper
NJC
2
3
4
5
6
7
8
9
J. Qiu, Y. Feng, X. Zhang, M. Jia and J. Yao, J. Colloid 24 J. Gong, H. Lin, M. Antonietti and J. Yuan, J. Mater. Chem. A,
Interface Sci., 2017, 499, 151–158. 2016, 4, 7313–7321.
N. N. Bahrudin, M. A. Nawi and W. I. N. W. Ismail, Korean 25 J. Gong, J. Liu, X. Chen, Z. Jiang, X. Wen, E. Mijowska and
J. Chem. Eng., 2018, 35, 1450–1461. T. Tang, J. Mater. Chem. A, 2015, 3, 341–351.
T. K. Mahto, S. Chandra, C. Haldar and S. K. Sahu, RSC Adv., 26 S.-B. Yu, H. Lyu, J. Tian, H. Wang, D.-W. Zhang, Y. Liu and
015, 5, 47909–47919. Z.-T. Li, Polym. Chem., 2016, 7, 3392–3397.
M. Afshari and M. Dinari, J. Hazard. Mater., 2020, 27 S.-X. Xu, Z.-Q. Yao and Y.-H. Zhang, Eur. Polym. J., 2020,
85, 121514. 133, 109764.
R. Saxena, M. Saxena and A. Lochab, ChemistrySelect, 2020, 28 N. Mokhtari, M. Afshari and M. Dinari, Polymer, 2020,
, 335–353. 195, 122430.
X. Li, H. Lu, Y. Zhang and F. He, Chem. Eng. J., 2017, 316, 29 S. K. Konavarapu and K. Biradha, Crystal Growth Design,
93–902. 2018, 19, 362–368.
E. Haque, J. W. Jun and S. H. Jhung, J. Hazard. Mater., 2011, 30 J. Huo, B. Luo and Y. Chen, ACS Omega, 2019, 4, 22504–22513.
2
3
5
8
1
85, 507–511.
S. Shakeri, Z. Rafiee and K. Dashtian, J. Chem. Eng. Data,
020, 65, 696–705.
31 Q. Pan, S. Chen, C. Wu, Z. Zhang, Z. Li and Y. Zhao, ACS
Appl. Mater. Interfaces, 2019, 11, 46070–46076.
32 S. Wang, Q. Wang, P. Shao, Y. Han, X. Gao, L. Ma, S. Yuan,
X. Ma, J. Zhou, X. Feng and B. Wang, J. Am. Chem. Soc., 2017,
139, 4258–4261.
2
1
1
1
1
1
0 M. A. Khan, Momina, M. R. Siddiqui, M. Otero,
S. A. Alshareef and M. Rafatullah, Polymers, 2020, 12, 500.
1 M. Rajabi, K. Mahanpoor and O. Moradi, RSC Adv., 2017, 7, 33 P. Pachfule, A. Acharjya, J. Roeser, T. Langenhahn, M. Schwarze,
4
7083–47090.
R. Schomacker, A. Thomas and J. Schmidt, J. Am. Chem. Soc.,
2018, 140, 1423–1427.
34 Y. Li, C. Wang, S. Ma, H. Zhang, J. Ou, Y. Wei and M. Ye,
ACS Appl. Mater. Interfaces, 2019, 11, 11706–11714.
35 X. Pan, X. Qin, Q. Zhang, Y. Ge, H. Ke and G. Cheng,
Microporous Mesoporous Mater., 2020, 296, 109990.
2 Y. Li, C.-X. Yang, H.-L. Qian, X. Zhao and X.-P. Yan, ACS
Appl. Nano Mater., 2019, 2, 7290–7298.
3 Q. Chen, Q. He, M. Lv, Y. Xu, H. Yang, X. Liu and F. Wei,
Appl. Surf. Sci., 2015, 327, 77–85.
4 K. Preet, G. Gupta, M. Kotal, S. K. Kansal, D. B. Salunke,
H. K. Sharma, S. Chandra Sahoo, P. Van Der Voort and 36 T. Geng, S. Ye, Z. Zhu and W. Zhang, J. Mater. Chem. A, 2018,
S. Roy, Crystal Growth Design, 2019, 19, 2525–2530. 6, 2808–2816.
5 N. Cheng, Q. Hu, Y. Guo, Y. Wang and L. Yu, ACS Appl. 37 H. Shin, J. Kim, D. Kim, V. H. Nguyen, S. Lee, S. Han, J. Lim
Mater. Interfaces, 2015, 7, 10258–10265. and K. Char, J. Mater. Chem. A, 2018, 6, 23542–23549.
6 L. Liu, Z. Y. Gao, X. P. Su, X. Chen, L. Jiang and J. M. Yao, 38 H. Ma, J.-J. Chen, L. Tan, J.-H. Bu, Y. Zhu, B. Tan and
ACS Sustainable Chem. Eng., 2015, 3, 432–442. C. Zhang, ACS Macro Lett., 2016, 5, 1039–1043.
7 A. Dey, S. K. Konavarapu, H. S. Sasmal and K. Biradha, 39 N. Huang, L. Zhai, H. Xu and D. Jiang, J. Am. Chem. Soc.,
Crystal Growth Design, 2016, 16, 5976–5984. 2017, 139, 2428–2434.
8 Y. Li, X. Hou, Y. Pan, L. Wang and H. Xiao, Eur. Polym. J., 40 J. H. Chong, M. Sauer, B. O. Patrick and M. J. MacLachlan,
020, 123, 109447. Org. Lett., 2003, 5, 3823–3826.
9 S. Mondal, U. Rana, P. Das and S. Malik, ACS Appl. Polym. 41 S. Ghorai, A. Sarkar, M. Raoufi, A. B. Panda, H. Schonherr
Mater., 2019, 1, 1624–1633. and S. Pal, ACS Appl. Mater. Interfaces, 2014, 6, 4766–4777.
0 M. S. Ramezani, J. Ozdemir, A. R. Khosropour and 42 R. Gong, J. Ye, W. Dai, X. Yan, J. Hu, X. Hu, S. Li and
1
1
1
1
1
2
2
M. H. Beyzavi, ACS Appl. Mater. Interfaces, 2020, 12,
4117–44124.
1 D. Wei, J. Li, Z. Chen, L. Liang, J. Ma, M. Wei, Y. Ai and
H. Huang, Ind. Eng. Chem. Res., 2013, 52, 14297–14303.
43 H. Lata, S. Mor, V. K. Garg and R. K. Gupta, J. Hazard.
Mater., 2008, 153, 213–220.
4
2
2
2
X. Wang, J. Mol. Liq., 2020, 301, 112431.
2 T.-X. Wang, H.-P. Liang, D. A. Anito, X. Ding and B.-H. Han,
J. Mater. Chem. A, 2020, 8, 7003–7034.
44 M. Firoozi, Z. Rafiee and K. Dashtian, ACS Omega, 2020, 5,
9420–9428.
45 J. Gong, J. Feng, J. Liu, Z. Jiang, X. Chen, E. Mijowska,
X. Wen and T. Tang, Chem. Eng. J., 2014, 248, 27–40.
3 X. Qian, Z. Q. Zhu, H. X. Sun, F. Ren, P. Mu, W. Liang,
L. Chen and A. Li, ACS Appl. Mater. Interfaces, 2016, 8, 46 Y. Wang, X. Cui, Y. Wang, W. Shan, Z. Lou and Y. Xiong,
1063–21069. New J. Chem., 2020, 44, 16285–16293.
2
This journal is The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2021
New J. Chem., 2021, 45, 3448ꢀ3453 | 3453