Synthesis and characterization of porous organic polymer containing tailored?AB3?metalloporphyrin: highly active?and reusable catalyst?for oxidation of benzyl alcohol

Article abstract of DOI:10.1007/s11164-021-04563-y

In this work, a modern and attractive Cu(II) porphyrin‐based polymer network with high surface area was synthesized. This strategy prepares an easy approach to produce highly stable Cu-Porphyrin‐based polymer network. The organization of this catalyst was

Full text of DOI:10.1007/s11164-021-04563-y

Research on Chemical Intermediates
https://doi.org/10.1007/s11164-021-04563-y
Synthesis and characterization of porous organic polymer
containing tailored AB metalloporphyrin: highly
3
active and reusable catalyst for oxidation of benzyl alcohol
1
1
1
Arash Mouradzadegun · Sheida Hamid · Asiyeh Sheikhzadeh Takabi
Received: 22 May 2021 / Accepted: 1 August 2021
©
The Author(s), under exclusive licence to Springer Nature B.V. 2021
Abstract
In this work, a modern and attractive Cu(II) porphyrin‐based polymer network with
high surface area was synthesized. This strategy prepares an easy approach to pro-
duce highly stable Cu-Porphyrin‐based polymer network. The organization of this
catalyst was certiꢀed by spectroscopic (ultraviolet–visible, Fourier transform infra-
red, powder X-ray diꢁraction, thermal gravimetric analysis, energy dispersive spec-
troscopy and scanning electron microscopy). Catalytic activity of Cu-Porphyrin-
based polymer network has been investigated for oxidation of benzyl alcohols to the
benzaldehydes. The results indicated that this catalyst displayed high catalytic activ-
ity and recycling eꢂciency in oxidation of benzyl alcohols.
Keywords Porphyrin · Polymer network · Benzyl alcohol · Metalloporphyrin
Introduction
Metalloporphyrins have engrossed signiꢀcant attention because of their diverse
physicochemical properties and their extensive scope of applications such as photo-
dynamic therapy, engineered molecular building blocks, nonlinear optical materials,
solar energy storage devices, bio- and optical sensors and metal adsorption [1–8].
Also, they have been perusaled in these systems as biomimetic catalysts of enzymes
such as the monooxygenases [9, 10]. Metalloporphyrins are present extracting major
regard because they have capability to catalyze a diversity of oxidation reactions
imitating P450 with O . However, the utilization of them as a catalyst in homoge-
2
neous oxidation processes has multiple drawbacks [11]. For case in point: (1) they
do display low selectivity and (2) it is hard to separate metalloporphyrins from the
reaction mixture, which make homogeneous catalysis a costly method in mercantile
*
Arash Mouradzadegun
arash_m@scu.ac.ir
1
Department of Chemistry, Faculty of Science, Shahid Chamran University of Ahvaz, Ahvaz,
Iran
Vol.:(012
1
3456789)
3

A. Mouradzadegun et al.
processes. Also, deactivation of acting sites is caused by association of porphyrin
loops by π–π interaction as the reaction proceeds [12]. The above-said problems
could be unraveled by ꢀxing them on the surface of solid materials. Since immo-
bilized porphyrins catalysts have the fewer of the disadvantages of homogeneous
catalysts, such as the problems in regeneration and recovery. However, a versatil-
ity of polymeric supports have been reported; some of them toil from one or more
faults in their attributes or synthetic ways, including multiplex steps for synthesis,
long reaction times, rude reaction status, the utilization of costly catalysts and solv-
ability in diꢁerent solvents and low chemical and/or thermal stability. In view of the
easiness of provision and the unique properties of the network polycalix[4] resor-
cinarene (PC4RA), such as multifaceted chemical rectiꢀcation, good dispersion of
active sites, its outspoken functionalization way via post-functionalization without
undergoing copolymerization or further post-polymerization, porous surface and
high chemical and thermal stability, it would be rational to consider this polymeric
structure as a promising starting substance for the synthesis of a new and eꢁective
porous organic polymer [13–26]. To the best of our scholarship, in spite of many
progresses in the plan, synthesis and usage of functionalized C4RA, there have been
no reports on its functionalization through covalently anchored metalloporphyrin
onto the overhead rim of C4RA. With the above mentioned, as part of our persistent
endeavors to expand high eꢂciency and environmentally favorable ways for varied
substantial reactions and conversions and due to our new fondness in the usage of
the PC4RA for the provision of carbonyl compounds. Here, we report the function-
alization of PC4RA through a covalently anchored metalloporphyrin and the exami-
nation of its performance as a heterogeneous and solid catalyst for the synthesis of
benzaldehyde compounds.
Experimental
Characterization
FTIR, EDX, XRD, NMR, SEM, ICP and UV–VIS were performed to determine the
as-prepared Cu-Porphyrin@ polymer samples. The empirical details about the utili-
zation of these characterization techniques are given in Supporting Information.
Procurement of 5‑(4‑carboxyphenyl)‑10, 15, 20‑triphenylporphyrin (1b)
4
-(methoxycarbonyl)phenyltriphenylporphyrin (1a) was prepared according to
Lindsay’s method [27, 28]. 2.0 mmol (p-methoxycarbonylbenzaldehyde), 6.0 mmol
Benzaldehyde) and 0.1 ml (BF ·OEt ) were added to a 500 ml chloroform solu-
(
3
2
tion and stirred for an hour. Then, 300 ml chloroform solution of pyrrole (0.56 ml;
8
9
.0 mmol) was added. After the solution color became violet, chloranil (2.2 g;
.0 mmol) and triethylamine (0.2 ml; 1.43 mmol) were added to the solution, and
then, the solution under nitrogen gas, it was heated to 80 °C for one hour. After
puriꢀcation and vaporization of the solvent, the compressed solution was drawn out
1
3

Synthesis and characterization of porous organic polymer…
with n-hexane/ethyl acetate (14:1, v/v). The ꢀnal products were exposed to column
chromatography on silica gel to produce.
In the subsequent step, to a purple solution of 1a (0.121 g) in 40 mL of triꢃuoro-
acetic acid (TFA), hydrochloric acid solution (35%; 25 ml) was added. Then, the
reaction was heated at 90 °C for 36 h. The reaction blend was drawn out with ethyl
acetate and water. An ethyl acetate layer was dried with Na SO to produce (1b) [29,
2
4
3
0] (Scheme 1).
5
‑[4‑(N‑(3‑triethoxysilylpropylbenzamido))]‑10, 15, 20‑triphenylporphyrin (1d)
After dissolving 1b in 5 ml of chloroform, thionyl chloride (500 μL, 6.884 mmol)
was added; then, the solution for 3 h was heated at 65 °C. After cooling the reac-
tion mix to ambient temperature, excess thionyl chloride and the chloroform were
eliminated under reduced compression (1c). The solid green remnant was dissolved
in waterless dichloromethane; then, (3-aminopropyl) triethoxysilane(80 μL) and tri-
ethylamine (160 μL) were added and reꢃuxed for 24 h, and then, the mixture was
cooled to ambient temperature. All excess materials were eliminated under reduced
compression, and the raw product by silica gel column chromatography was puriꢀed
(
1c) [30, 31] (Scheme 1).
5
2
‑[4‑(N‑(3‑triethoxysilylpropylbenzamido))]‑10, 15,
0‑triphenylporphinatocopper (II) (1e)
After dissolving 1c (0.058 mmol) in methylene chloride (20 mL), copper (II) acetate
(
1.156 mmol) was added. For 12 h, the reaction blend was stirred at ambient tem-
perature. Then, the solvent of reaction was eliminated under reduced compression.
The remnant was purged by column chromatography on silica gel with hexane/ethyl
acetate as eluent [32] (Scheme 1).
Synthesis of calix [4] resorcinarene (C4RA) (2a)
(
2a) was readied according to a formerly reported method [33] (Scheme 1).
Synthesis of network polycalix [4] resorcinarene (PC4RA) (2b)
3
To 14 mmol of previously synthesized C4RA in 40 cm NaOH solution (10%),
4
2 mmol of formaldehyde was added dropwise at ambient temperature. After ꢀnali-
zation of formaldehyde addition, for 20 h the blend was heated at 90 °C. The surplus
alkali was washed out from the outcome gel with cold water. Next, the gel became
acidic in treatment with 0.1 M HCl solution. Lastly, the solid outcome was dried at
1
00 °C for 10 h[34] (Scheme 1).
1
3

A. Mouradzadegun et al.
Ph
Ph
CHO
CHO
H
N
1-BF3
-
N
HN
N
N
HN
N
1. CF3CO2
H
Et2O, rt
CO2Me
CO2
H
3
4
Ph
Ph
2
-DDQ, NEt3
NH
2. HCl
NH
reflux
CO2Me
Ph
Ph
1b
1
a
OEt
Si
EtO
OEt
HN
Ph
NH2
TEA
reflux 24 h
Ph
O
N
HN
,
DCM
N
H
SOCl2
1
b
Ph
COCl
EtO Si
EtO
N
NH
N
OEt
N
H
N
Ph
Ph
Ph
1
c
1
d
OEt
OEt
EtO
OEt
EtO
OEt
Si
Si
HN
HN
Ph
Ph
O
O
N
N
H
Cu(OAC)2
N
N
N
M
N
H
N
CHCl2, 12 h, rt
Ph
Ph
N
Ph
Ph
1
e
H
H
H2C
HO
OH
HO
OH
H
HO
HO
OH
HO
OH
HO
4
OH
O
C
CH3
CH3
H3C
H3C
CH3 H3C
H2
HCl
O
C
NaOH
C
4
H3C
H
H
H
CH3 H3C
HO
OH
OH
HO
OH
HO
OH
H2C
b
n
2
2
a
Ph
OEt
Si
N
Ph
EtO
OEt
N
M
N
O
N
Ph
NH
HN
Ph
O
N
Si
O
N
O
M
O
N
N
Ph
Ph
Toluene , 90 0
C
PC4RA
=
Scheme 1 Synthesis of Cu-porphyrin@ PC4RA
1
3

Synthesis and characterization of porous organic polymer…
Synthesis of Cu‑Porphyrin immobilized on network PC4RA
In a round-bottom ꢃask containing 10 mL toluene, 10 mg of PC4RA and 5 mg of
(
1e) were added at ambient temperature. After heating reaction mixture to 90 °C
for 24 h, the resulting solid for several times washed with deionized water and then
dried at 70 °C[30] (Scheme 1).
Typical method for oxidation of benzyl alcohol
2
mmol of benzyl alcohol, 6 mmol of isobutyraldehyde, 10 ml of O-Xylol as solvent
and 20 mg of catalyst were added in a 25 mL two-neck ꢃask and heated at 55 °C.
The mixture was stirred with the oxygen gas pumping into the system. After the
reactions, the catalyst was ꢀltered for several times, washed with methanol and then
dried under vacuum before being devoted to the next catalytic cycle (Scheme 2).
Also the product was analyzed by gas chromatograph (GC) to characterize the prod-
uct and reactant concentrations.
Results and discussion
As reported before, in modern chemistry, one of the most agitating challenges
is the probe for more eꢁective catalytic systems that might blend the privileges
of both homogeneous and heterogeneous catalysis. In light of this fact, we pre-
pared Cu-Porphyrin@ PC4RA as a novel catalyst to produce of carbonyl com-
pounds. In the ꢀrst stride, the reaction of resorcinol and acetaldehyde resulted in
C4RA formation which in the next step, under polycondensation with formalde-
hyde produced the polymeric network (Scheme 1) [33, 34]. Formation of com-
pounds 2a and 2b was corroborated through a series of spectroscopic analysis
(
see ESI) [35]. In the second step, the porphyrin ligand was synthesized accord-
ing to previous reports [28–30, 36]. In the following, the porphyrin complex was
reacted with 3-aminopropyltriethoxysilane (APTES) [30, 31]. Then, the porphy-
rin ligand was metalated (1e). Subsequently, metalloporphyrin immobilized on
PC4RA (2b) was produced as the outcome of the reaction between compound
(
2b) and compound (1e) (Scheme 1). In order to characterize the catalyst, and
to corroborate the covalent interactions between metalloporphyrin and PC4RA
in metallporphyrin@ PC4RA, FTIR was recorded (Fig. 1). The IR spectrum of
−
1
the functionalized Cu-Porphyrin@ PC4RA appearance a new peak at 1552 cm
is due to C–N stretching and N–H bending vibrations conꢀrmed the bond of the
O
OH
Cu-porphyrin@PC4RA (20 mg)
o
O / Isobutyraldehyde, O-xylene, 55 C
2
H
Scheme 2 The oxidation benzyl alcohol by Cu-porphyrin@ PC4RA and molecular oxygen
1
3

A. Mouradzadegun et al.
Fig. 1 FTIR spectra of (a) synthesized porphyrin (b) PC4RA (C) Cu-Porphyrin@ PC4RA
−
1
amide group and a wide peak at 1109 cm , which is showman of Si–O bonds.
−
1
On the other hand, a wide peak at 3210–3555 cm displayed that all of the OH
groups of PC4RA (2b) are not totally functionalized due to steric impediment.
So, the FTIR data qualitatively corroborated the prosperous grafting of Si groups
onto the surface of the polymer (Fig. 1). In addition to FTIR spectrum, other
techniques were considered for better catalyst veriꢀcation (UV–VIS, SEM, XRD,
EDX and TGA). Furthermore, the UV–Vis spectrum of porphyrin displays peaks
at 413 (Soret band), 513, 547, 590 and 645 nm (Q bands). Upon copper ion con-
catenation, the pyrrole nitrogen’s of porphyrin are coordinated to the copper ion
to form Cu‐Porphyrin complex. As a result, the intensity of Q peaks is reduced,
and the Soret peak displays slight red shift (from 413 to 425 nm) that is charac-
teristic of the creation of Cu‐Porphyrin complex (Fig. 2). The EDS analysis was
applied to assess the catalyst, which corroborates the presence of N, Si and Cu in
the mentioned precatalyst (Fig. 3). In order to achieve an intuition into the mor-
phology of the synthesized catalyst, SEM was used (Fig. 4). Since the catalyst
Fig. 2 UV–Vis spectrums of porphyrin (a) and Cu-Porphyrin@ PC4RA (b)
1
3

Synthesis and characterization of porous organic polymer…
Elt
C
W%
40.57
8.59
32.47
8.83
1.03
8.51
N
O
Si
Cl
Cu
Fig. 3 EDS result for Cu-Porphyrin@ PC4RA
shows smaller pores than PC4RA (see ESI†), it can be derived that the Cu-Por-
phyrin are successfully ꢀxed onto the polymeric spines. The pattern of XRD is
conꢀrmed the Cu-Porphyrin@ PC4RA structure (Fig. 5). The thermal stability of
Cu-Porphyrin@ PC4RA was investigated by TGA analysis. The primary negligi-
ble weight loss happens before 145 °C, which can be imputed to the vaporization
of water or extant solvent. The second loss weight is happened at 145–400 °C,
which attributed to the dissociation of Cu-Porphyrin. Thus, TGA analysis shows
the high thermal constancy of Cu-Porphyrin@ PC4RA. The third loss weight is
1
3

A. Mouradzadegun et al.
Fig. 4 The SEM image of Cu-Porphyrin@ PC4RA
Fig. 5 XRD patterns of Cu-Porphyrin@ PC4RA
Fig. 6 TGA curves of Cu-Porphyrin@ PC4RA
1
3

Synthesis and characterization of porous organic polymer…
attributed to dissociation of PC4RA at ~ 460 °C (Fig. 6). To evaluate the cata-
lytic activity of Cu-Porphyrin@ PC4RA in the oxidation reactions, the reaction
of benzyl alcohol was chosen as a model system to get eꢂcient results. We stud-
ied various conditions, including amount of catalyst, solvents, temperature and
isobutyraldehyde, the outcomes of which are tabloid in Table 1. From Table 1,
the best result was obtained when the reaction was done in the presence of 20 mg
of Cu-Porphyrin@ PC4RA. To investigate the eꢁect of solvent, the reactions with
diꢁerent solvent were conducted. It seemed that the solvent played a key role in
the oxidation system. As shown in Table 1, O-Xylene solvent was suitable to the
oxidation reaction, which gave high yield of benzaldehyde (entry 3). However,
when water, acetonitrile, ethanol and chloroform were used instead, trace product
could be obtained (entries 9–12). The benzyl alcohol oxidation catalyzed by met-
alloporphyrin should involve radical species. So, O-Xylene as solvent is mostly
the election for radical reactions because of its disinclination to undergo radical
addition. Also the temperature eꢁect was studied on oxidation of benzyl alcohol.
With increase temperature from 40 to 55 °C, it was indicated that the conver-
sion eꢂciency increased. It is remarkable, when temperature was raised benzoic
acid could detect (entry 8). The eꢁect of isobutyraldehyde as co-catalyst played
a signiꢀcant role in the oxidation reaction (Table 2). It should be noted that in
the lack of co-catalyst, these oxidation reactions require longer time. Also, the
catalyst (Cu-Porphyrin@ PC4RA) shows high activity compared to free metal-
loporphyrin (Table 2). In this reaction method, a wide range of benzyl alcohols
have been oxidized that diꢁerent substitutions including electron-withdrawing or
electron-donating groups had good and excellent outputs (Table 3) without any
by-products. It seems that the performance of oxidation in these catalytic systems
Table 1 The eꢁect of solvent on the oxidation of benzyl alcohol by O in the presence of Cu-Porphyrin@
2
PC4RA
o
Entry
Amount of
Temperature C
Solvent
Time
(h)
Yield%
catalyst(mg)
1
2
3
4
5
6
7
8
9
5
10
20
30
20
20
20
20
20
20
20
20
55
55
55
55
25
40
55
70
reꢃux
reꢃux
reꢃux
reꢃux
O-Xylene
O-Xylene
O-Xylene
O-Xylene
O-Xylene
O-Xylene
O-Xylene
O-Xylene
Water
6
6
6
6
6
6
6
6
6
6
6
6
55
75
94
95
30
60
94
85
30
25
50
40
10
11
12
Ethanol
Acetonitrile
Chloroform
Reaction condition: Benzyl alcohol (2 mmol), isobutyraldehyde (6 mmol), catalyst (20 mg), O-Xylene
10 ml), O (1 atm), 55 °C
(
2
1
3

A. Mouradzadegun et al.
Table 2 Comparison between Cu-Porphyrin@ PC4RA and Cu-Porphyrin in the presence of isobutyral-
dehyde
Entry
Cu-Porphyrin@
PC4RA(mg)
Cu-Porphyrin(mg) Isobutyraldehyde(mmol)
Time(h)
Yield%
1
2
3
4
5
6
20
20
20
20
–
–
–
–
–
20
–
–
2
4
6
6
6
6
6
6
6
6
6
40
60
85
94
55
25
–
Reaction condition: Benzyl alcohol (2 mmol), O-Xylene (10 ml), O (1 atm), 55 °C
2
is much related to the electronic and space needs of the substrate (Table 3). The
recovery capability from the reaction medium and activity is considered as one of
the most important characteristics of the solid catalyst. Thus, we checked the pos-
sibility of recovering Cu-Porphyrin@ PC4RA in the oxidation reactions. So, after
the each reaction completion, Cu-Porphyrin@ PC4RA was recovered from the
reaction mix by easy puriꢀcation, washed with methanol and hot water, and after
drying it was ready to be utilized anew in the following analogous cycle and then
reusing the catalyst up to ꢀve times without signiꢀcance loss of activity (Fig. 7).
The amount of Cu in the sample was conꢀrmed with ICP technique. Respectively,
the weight percentage of copper in fresh and reused catalyst (after ꢀve times) was
2
0.2wt% and 20.17wt%. On these results, we can conclude that there is no con-
siderable diꢁerence in weight percentage of copper in reused and fresh catalyst
that was used in the primary time in the reaction. Also, this veriꢀcation showed
that Cu linked with porphyrin ring and these linkages are ꢀrm. In addition, no
leaching occurs in reaction medium.
Conclusions
In this research, at ꢀrst, 4-(methoxycarbonyl)phenyltriphenylporphyrin was pre-
pared according to Lindsay’s method. Then, 4-(methoxycarbonyl)phenyltriphe-
nylporphyrin immobilized on network PC4RA, as an eco-friendly solid-supported
catalyst, was successfully prepared and characterized by FTIR, TGA, SEM, XRD,
ICP and EDS. This catalytic activity was investigated in the oxidation of alco-
hols in present O . This way renders signiꢀcant beneꢀts including simple work-
2
up method, short reaction times, good consistency, operational simplicities, clean
reaction proꢀles, cost-eꢁective method, ease of separation and recyclability of the
solid catalyst.
Supplementary Information The online version contains supplementary material available at https://doi.
org/10.1007/s11164-021-04563-y.
1
3

Synthesis and characterization of porous organic polymer…
Table 3 The oxidation of benzyl alcohols in present O and Cu-Porphyrin@ PC4RA
2
Entry
Alcohol
Product
Time(h)
Conversion%
94
O
OH
1
6
H
O
OH
2
6
88
H
OMe
OH
Cl
OMe
O
H
OH
3
4
6
6
90
85
MeO
MeO
O
H
OH
OH
O
OH
5
6
8
90
HO
H
HO
O
H
OH
6
9
0
Cl
O
OH
7
8
8
8
75
60
Cl
H
Cl
O
OH
O N
2
H
2
O N
OH
O
9
8
94
Reaction condition: Benzyl alcohol (2 mmol), isobutyraldehyde (6 mmol), catalyst (20 mg), O-Xylene
10 ml), O (1 atm), 55 °C
(
2
1
3

A. Mouradzadegun et al.
1
1
20
00
9
4
9
0
8
8
8
6
4
2
0
0
0
0
0
85
85
No. of cycles
Fig. 7 Recyclability of catalyst
Funding Funding was provided by Shahid Chamran University of Ahvaz (Grant Number SCU.
SC98.357).
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