Functionalized resorcin[4]arene-based coordination polymers as heterogeneous catalysts for click reactions

Article abstract of DOI:10.1039/d0nj06051h

Three distinctive coordination polymers [Cu₂L₂]·0.5CH₃OH·1.5H₂O·2CN (1), [CdCl₂L]·5DMF·2CH₃OH·2H₂O (2) and [Cd₂L(bdc)₂(DMF)]·2DMF·3CH₃OH·H_2<

Full text of DOI:10.1039/d0nj06051h

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Functionalized resorcin[4]arene-based
coordination polymers as heterogeneous catalysts
for click reactions†
Cite this: New J. Chem., 2021,
45, 3181
Fei-Fei Wang,‡a Jia-Hui Li,‡a Hai-Yan Liu,b Shu-Ping Deng,b Ying-Ying Liu *a and
a
Jian-Fang Ma
*
Three distinctive coordination polymers [Cu2L2]Á0.5CH3OHÁ1.5H2OÁ2CN (1), [CdCl2L]Á5DMFÁ2CH3OHÁ2H2O (2)
and [Cd2L(bdc)2(DMF)]Á2DMFÁ3CH3OHÁH2O (3) were solvothermally synthesized using a resorcin[4]arene ligand
(H2bdc = p-phthalic acid and L = tetrakis(4-mercaptopyridine-ylmethyl)resorcin[4]arene). Among them, 1
exhibits a 3D structure, but 2 and 3 are both charming layers. 1 exhibits efficient and selective catalytic
performance for azide–alkyne cycloaddition reactions owing to its rich Lewis acid sites. Remarkably, as a hetero-
geneous catalyst, 1 could be recycled with preservation of the catalytic capability and structural integrity.
Received 12th December 2020,
Accepted 13th January 2021
DOI: 10.1039/d0nj06051h
rsc.li/njc
substituents provide multiple coordination sites when reacting
with metal ions.31–34 Scores of CPs with various structures and
Introduction
The alkyne and azide cycloaddition (AAC) reaction, a ‘‘click’’ reaction properties have been continuously employed based on
is a milestone method in the synthesis of 1,2,3-triazoles.1–3 Com- functional-resorcin[4]arene macrocyclic ligands. As to the cat-
pared with the classical Huisgen azide–alkyne 1,3-dipolar cycloaddi- alytic properties of resorcin[4]arene-based CPs, several groups
tion reactions, Cu(I)-based AAC reactions exhibit obvious have carried out research on this topic. Pioneering research
advantages, like extremely high regioselectivity, mild reaction con- studies suggest that resorcin[4]arene-based CPs show efficient
ditions, easy operation, and high yields.4–7 Therefore, CuAAC reac- catalytic performances in epoxidation of olefins,35 Knoevenagel
tions have been widely utilized in organic synthesis,8,9 medicinal condensation,36 oxidation desulfurization,37 C–H oxidation of
chemistry,10,11 chemical biology,12–14 and materials science.15,16 fluorene,38 and click reactions.39
Focusing on this reaction, a lot of Cu-based catalysts have been
In this study, we prepared a functional resorcin[4]arene
developed. CuCl, CuBr and CuSO4/reducers are typical homoge- ligand modified by four 4-mercapto-pyridine groups. Through
neous catalysts.17,18 But they feature the disadvantage of easy- the assembly of cadmium and copper salts with L, [Cu2L2]Á
destruction or difficulty in separating from the reaction system.19 0.5CH3OHÁ1.5H2OÁ2CN (1), [CdCl2L]Á5DMFÁ2CH3OHÁ2H2O (2)
In order to improve the catalytic efficiency, heterogeneous catalysts, and [Cd2L(bdc)2(DMF)]Á2DMFÁ3CH3OHÁH2O (3) have been
such as Cu(I)-based coordination polymers (CPs), have been synthesized successfully. Significantly, 1 exhibits good hetero-
developed.20–27
geneous catalytic capability for AAC reactions in the formation
Resorcin[4]arene, as a subclass of calix[4]arenes, has unique of 1,2,3-triazoles as well as b-OH-1,2,3-triazoles.
cavities and various functional moieties.28–30 Their mainbody
and rims could be modified by a number of groups, and these
Experimental section
Synthesis of L
a Key Lab of Polyoxometalate Science, Department of Chemistry, Northeast Normal
University, Changchun 130024, China. E-mail: liuyy147@nenu.edu.cn,
majf247@nenu.edu.cn
b Key Lab of Chemical Additive Synthesis and Separation, Department of Chemical
and Environmental Engineering, Yingkou Institute of Technology, Yingkou 115014,
China
First, we synthesized precursor L1 by using the reported method.40
L1 (10.0 mmol), anhydrous K2CO3 (100.0 mmol), 4-mercapto-
pyridine (50.0 mmol) and DMF (200 mL) were added to the
flask in turn and heated at 90 1C under N2 for 10 hours. The
reaction was monitored by thin layer chromatography. Then,
the obtained solid was suction filtrated, rotary evaporated and
washed with water. The crude product was recrystallized using
CH2Cl2–CH3OH to obtain light yellow L with a yield of 85%
(Scheme 1 and Fig. S1–S3, ESI†).
† Electronic supplementary information (ESI) available. CCDC crystallographic
data and structure refinements, PXRD patterns, infrared spectra, TGA curves,
selected bond distances and angles of 1–3, GC and 1H NMR of the AAC reactions
are provided. CCDC 2048218–2048220 for 1–3. For ESI and crystallographic data
in CIF or other electronic format see DOI: 10.1039/d0nj06051h
‡ These authors contributed equally.
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Scheme 1 Schematic synthesis of L.
Synthesis of [Cu2L2]Á0.5CH3OHÁ1.5H2OÁ2CN (1)
Cu(NO3)2Á2H2O (10 mg, 0.04 mmol), L (11 mg, 0.01 mmol),
fumaric acid (5 mg, 0.04 mmol) and DMF/methanol V/V = 5/3
were added to a 15 mL vessel and reacted at 100 1C for three
days. After cooling, pale green massive crystals were isolated.
The yield was calculated to be 53% based on L. Anal. calcd for
C
122.5H109N10O18S8Cu2 (Mr = 2390): C, 61.51; H, 4.56; N, 5.86; S,
10.71; found: C, 55.07; H, 4.71; N, 5.83; S, 9.60; IR (cmÀ1):
3421(w), 2970(w), 2942(w), 2882(w), 1656(w), 1588(s), 1532(w),
1474(m), 1416(m), 1384(m), 1333(m), 1253(m), 1211(w),
1148(w), 1104(s), 1092(m), 1051(w), 1017(m), 977(s), 932(m),
807(m), 754(w), 717(m), 689(w), 646(w), 579(w), 564(w), 493(w)
(Fig. S5, ESI†).
Fig. 2 (a) Coordination environment of Cd1 in 2. (b) View of the 2D layer.
(c) The 3D supramolecular structure constructed via H-bonds.
Synthesis of [CdCl2L]Á5DMFÁ2CH3OHÁ2H2O (2)
CdCl2Á2.5H2O (10 mg, 0.04 mmol), L (12 mg, 0.01 mmol),
proline acid (5 mg, 0.04 mmol) and DMF/methanol (V/V = 3/1)
were reacted at 100 1C for three days. After cooling, transparent
crystals were obtained (yield
=
44%). Anal. calcd for
C82H97N9O8S4Cl2Cd (Mr =1732.4): C, 56.79; H, 5.59; N, 7.27; S,
7.38; found: C, 50.61; H, 5.35; N, 6.60; S, 7.65; IR (cmÀ1): 3430(w),
2967(w), 2938(w), 2877(w), 1662(s), 1581(s), 1458(m), 1421(m),
1379(m), 1338(w), 1301(w), 1249(w),1220(w), 1146(w), 1092(m),
1047(w), 1006(m), 977(s), 920(m), 809(w), 719(w), 657(w), 584(w),
498(w).
Fig. 3 (a) Coordination environment of Cd1 and Cd2 ions in 3. (b) View of
the 2D layer. (c) The 3D supramolecular structure.
Synthesis of [Cd2L(bdc)2(DMF)]Á2DMFÁ3CH3OHÁH2O (3)
CdCl2Á2.5H2O (10 mg, 0.04 mmol), L (11 mg, 0.01 mmol),
p-H2bdc (7 mg, 0.04 mmol) and DMF/methanol V/V = 6/2 were
reacted at 100 1C for three days. Light yellow massive crystals
were obtained (yield
= 14%). Anal. calcd for C103H115
N10O28S4Cd2 (Mr = 2291): C, 53.95; H, 5.02; N, 6.11; S, 5.58;
found: C, 50.18; H, 5.63; N, 5.92; S, 5.49; IR (cmÀ1): 3430(w),
2933(w), 2270(w), 1661(s), 1591(s), 1556(s), 1502(m), 1469(m),
1385(s), 1250(w), 1227(w), 1147(w), 1094(m), 1051(w), 1013(m),
976(s), 928(w), 842(w), 807(w), 754(m), 720(w), 685(w), 662(w),
581(w), 496(w).
Fig. 1 (a) Coordination environments of Cu1 and Cu2 in 1. (b) The 3D
framework.
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Table 1 The AAC reactions under different conditions
TONa
TOFb (hÀ1
)
Catalyst (mg)
Entry
Time (h)
Temperature (1C)
Solvent
Conversion (%)
1
2
3
4
5
6
7
None
5
5
5
5
5
5
5
80
80
80
80
RT
40
60
MeOH
MeOH
EtOH
MeCN
MeOH
MeOH
MeOH
13
499
96
27
3
23
64
0
0
5
5
5
5
5
5
471
457
129
14
110
61
94.2
91.4
25.8
2.8
22.0
61.0
a
b
Per-mole catalyst for mole product. Per-mole catalyst per-hour for mole product.
Table 2 AAC catalytic reaction with different substituentsa
Entry
1
Azide
Alkyne
Product
Conversion (%)
99
TON
TOF (hÀ1
94.2
)
471
471
2
3
99
99
94.2
94.2
471
471
471
4
5
99
99
94.2
94.2
6
7
88
33
56
419
157
267
83.8
31.4
53.4
8
a
Reaction conditions: catalyst (5 mg, 0.21% mmol), azide (1 mmol), acetate (0.92 mmol), alkyne (2 mmol) and MeOH (4 mL), 80 1C, 5 h.
Results and discussion
Structure of [Cu2L2]Á0.5CH3OHÁ1.5H2OÁ2CN (1)
vertical arrangement (Fig. 1b). All the N atoms on the L
participate in the coordination. By this method, Cu(I) ions are
connected by L ligands to form a noteworthy 3D framework
(Fig. 1b).
The independent unit of 1 constitutes two Cu(I) ions, one whole
and two half L ligands, one half free CH3OH, one and a half free
H2O and two CNÀ anions (Fig. 1a). The free CNÀ anions came
from the disintegration of DMF, which balanced the cationic
Structure of [CdCl2L]Á5DMFÁ2CH3OHÁ2H2O (2)
charges of the structure.41,42 Both Cu1 and Cu2 are four- The independent unit of 2 contains one Cd(II) ion, one L, two
ClÀ anions, five free DMF, two free CH3OH and two free H2O
coordinated in regular tetrahedral geometries, defined by four
L ligands, respectively. Three individual bowl-shaped L ligands
extended in two directions, of which two half-occupied L
ligands are in horizontal arrangement, and the third one is in
molecules. Cd1 is located at an inversion center, and is six-
coordinated by four pyridyl N atoms from four L ligands and
two ClÀ anions (Fig. 2a). All N atoms of L ligand participate in
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on both sides of the layer (Fig. 3b). Due to the existence of hydrogen
bonds (C36ÁÁÁO12
=
3.238Å, +C36–H36BÁÁÁO12
= 123.551,
C44ÁÁÁO10 = 3.300Å, +C44–H44ÁÁÁO10 = 124.111), the thick layers
are further connected to form a fascinating 3D supramolecular
structure (Fig. 3c).
Catalytic performance of 1 for AAC reactions of benzyl azide
Considering that CP 1 has efficient Lewis acid Cu(I) active sites,
1 was used for catalytic AAC reactions. In the experiment,
phenylacetylene and benzyl azide were used as the basic
substrates to explore the suitable reaction conditions
(Table 1). The conversions were calculated by gas chromato-
graphy (Fig. S7, ESI†).
First, the reaction was carried out without adding any
catalyst, and a conversion of 13% was achieved (entry 1).
Subsequently, to investigate suitable solvents, the catalytic
performances were studied in MeCN, EtOH and MeOH. The
highest conversion was obtained in MeOH (99%), while the
conversions in the other two solvents were 96% and 27%,
respectively (entries 2–4). So in the following experiments,
MeOH was utilized as the optimal solvent. Next, the experi-
ments were conducted at different temperatures, and lower
conversions of 3%, 23% and 64% were obtained at RT, 40 1C
and 60 1C, respectively (entries 5–7).
Fig. 4 Kinetic (blue) and hot filtration (pink) experiments catalyzed by
1 for phenylacetylene and benzyl azide reaction.
the coordination, and the ligands link Cd(II) ions to form a
charming layered structure (Fig. 2b). The bowl-shaped ligands
of each layer are inserted into two adjacent layers, resulting in
an interlocked 3D supramolecular structure. Most strikingly,
the existence of hydrogen bonds among the interspersed layers
further strengthens the 3D supramolecular architecture
(C12Á Á ÁO3 = 3.138Å, +C12–H12BÁ Á ÁO3 = 119.881, Fig. 2c). Cal-
culated by PLATON, the total potential solvent volume occupies
about 43.7% of the unit cell (2482.4 and 5299.4 Å3, respectively).
To further determine the general applicability of catalyst 1 to
AAC reactions, a series of azides and alkynes with different
functional groups were investigated under suitable reaction
conditions (Table 2 and Fig. S8, S9–S16, ESI†).
Structure of [Cd2L(bdc)2(DMF)]Á2DMFÁ3CH3OHÁH2O (3)
There exist two Cd(II) atoms, one ligand, two bdc anions, one
When benzyl azide with 4-CH3-, 3-CH3-, 2-F- and 4-NO2
coordinated DMF molecule, two free DMF, three free CH3OH substituents reacted with phenylacetylene respectively, the
and one free H2O molecule in the asymmetric unit of 3 (Fig. 3a). conversions all could reach 99% (entries 1–5), which demon-
Both Cd1 and Cd2 are seven-coordinated in pentagonal bico- strated that 1 has high catalytic efficiency in these reactions no
nical configurations. Cd1 is surrounded by two N atoms from matter whether the substituent is an electron-donating or
two L ligands and five O atoms from three bdc anions, whereas electron-withdrawing group. But when the benzyl azide reacted
the coordination geometry of Cd2 is completed by one N atom with phenylacetylene derivatives, the conversions decreased
from L ligand, six O atoms from three bdc anions and one significantly. When the substituent was 4-CH3-, the conversion
DMF. The bdc anions connect Cd(II) atoms into a layer. Only was 88% (entry 6). As for 4-F- and 4-Cl- substituents, the
three pyridyl N atoms of each L ligand participate in the conversions were as low as 33% and 56%, respectively (entries
coordination with Cd(II) ions. L ligands are regularly located 7 and 8). The results demonstrate that when benzyl azide
Fig. 5 (a) The conversions of cycling experiments catalyzed by 1 for phenylacetylene and benzyl azide reaction. (b) PXRD patterns of the simulated, the
experimental and after the 4th catalytic cycle.
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Table 3 The AAC reactions of phenylacetylene and 1-azido-2-hexanol
Entry
Catalyst (mg)
Time (h)
Temperature (1C)
Solvent
Conversion (%)
1
2
3
4
5
6
7
8
9
None
5
8
8
8
8
8
8
8
8
8
80
80
80
80
80
80
RT
40
60
MeOH
MeOH
MeOH
MeOH
EtOH
MeCN
MeOH
MeOH
MeOH
2
78
96
95
95
23
4
10
15
10
10
10
10
10
26
78
Table 4 AAC catalytic reaction of different functional groups of b-OH azides with phenylacetylenesa
Entry
1
Alkynes
Azides
Product
Conversion (%)
91
2
3
96
99
4
82
80
5
a
Reaction conditions: catalyst (10 mg, 0.42% mmol), b-OH azide (2 mmol), alkyne (1 mmol), and ethylbenzene (106 mg, 1 mmol) as an internal
standard, MeOH (4 mL), 80 1C, 8 h.
reacted with phenylacetylene derivatives, an electron-donating
group results in higher conversion than an electron-
withdrawing group.43,44
To study the reaction process, a kinetic test was started and
the conversions were monitored every hour. The conversion
increased rapidly to 93% within 4 hours. Then, it gradually
reached 99% within the next hour. To identify the heteroge-
neous quality of 1 for the AAC reaction, hot filtration was
conducted after the reaction proceeded for 1 hour. The conver-
sion of the remaining filtrate did not increase significantly in
the next 4 hours (Fig. 4 and Fig. S17, ESI†). Notably, the ICP test
demonstrated that no Cu(I) ions were observed in the filtrate.
This fully shows that 1 is a heterogeneous catalyst.
Then, cycling experiments were conducted. After four suc-
cessive runs, the conversions of the reactions did not change
and remained at 99% (Fig. 5a and Fig. S18, ESI†). After the
catalytic reaction, the PXRD curve of the catalyst was almost the
Fig. 6 Kinetic (blue) and hot filtration (pink) experiments catalyzed by 1
for 1-azido-2-hexanol and phenylacetylene reactions.
same as the simulation one (Fig. 5b).
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Fig. 7 (a) The conversions of cycling experiments catalyzed by catalyst 1 for 1-azido-2-hexanol and phenylacetylene reaction. (b) PXRD patterns of the
simulated, experimental, and after 4th catalytic cycles in 1-azido-2-hexanol and phenylacetylene reaction.
Catalytic propertiesy of 1 for b-OH azide AAC reactions
In the following cycling tests, the conversion after four
successive runs had only a slight decrease from 96% to 92%
(Fig. 7a and Fig. S27, ESI†). Remarkably, the PXRD curve of 1
after four catalytic experiments matched well with its original
one (Fig. 7b), exhibiting that the structure of 1 did not change.
Thus, the recycling experiments further proved the reusability
of 1.
To date, most CuAAC reactions have been focused on the
substrates of alkyl azides or aryl azides, and b-OH-substituted
azides have rarely been researched.45,46 Since 1 exhibits good
catalytic activity for phenylacetylene, we further expanded our
exploration to other types of substrates, that is b-OH azides.
First, phenylacetylene and 1-azido-2-hexanol were utilized as
model substrates to study the impact of several parameters
(dosage, solvent, temperature and time) on the catalytic reac-
tion (Table 3 and Fig. S19, ESI†). Under the conditions of
without a catalyst, the conversion was only 2% (entry 1). When
1 was added to the reaction, and the mass of the catalyst was 5,
10 and 15 mg, the conversions were 70%, 96% and 95%,
respectively (entries 2–4). So in the follow-up experiment,
10 mg was used as the catalyst dosage. The next reactions
were performed in three solvents, MeOH, EtOH and MeCN. A
maximal conversion of 96% was obtained in MeOH compared
with the other two solvents (entries 5 and 6). By varying the
temperature, lower conversions of 4%, 26% and 78% were
achieved at RT, 40 1C and 60 1C, respectively (entries 7–9).
To further assess the general usability, we expanded the scope of
substrates of catalyst 1 (Table 4 and Fig. S20, S21–S25, ESI†). When
4-F-phenylacetylene reacted with 1-azido-2-hexanol, the con-
version could reach 91% (entry 1). When phenylacetylene reacted
with 1-azido-2-hexanol, 1-azido-2-pentanol, 1-azido-2-butanol and
1-azido-3-phenoxy-2-propanol, the conversions of 96%, 99%, 82%
and 80% were obtained, respectively (entries 2–5). The results
indicate that 1 exhibits efficient catalytic performance for these
reactions.
Conclusions
In summation, one Cu(I) and two Cd(II) CPs were successfully
assembled by incorporating a 4-mercaptopyridine-functionalized
resorcin[4]arene ligand with metal ions. 1 displays a fascinating 3D
structure, and 2 and 3 exhibit layered structures. Strikingly, 1
exhibits an efficient catalytic activity in AAC reactions. It has good
stability and could be easily separated from catalytic systems. After
cycling, 1 could retain efficiency and its integry was maitained. The
catalytic experiments illustrate that 1 is a splendid heterogeneous
catalyst for the synthesis of 1,2,3-triazoles as well as b-OH-1,2,3-
triazoles.
Author contributions
Fei-Fei Wang: Investigation. Jia-Hui Li: Software and writing-
original draft. Hai-Yan Liu: Visualization. Shu-Ping Deng:
Resources. Ying-Ying Liu: Data curation, validation, and
writing – review & editing. Jian-Fang Ma: Conceptualization and
funding acquisition.
A kinetic reaction was studied with phenylacetylene and 1-azido-
2-hexanol in MeOH at 80 1C. In the first two hours, 62% conversion
was rapidly achieved. Then a gradual increase was observed, and
reached 96% in the next six hours. To testify the heterogeneity of
the reaction, 1 was separated by filtration after 2 hours. Then the
reaction went on under the same conditions, and the conversion
only has a slight increase of 3% (Fig. 6 and Fig. S26, ESI†). ICP data
showed that Cu(I) was not observed in the filtrate.
Conflicts of interest
There are no conflicts to declare.
Acknowledgements
This work was supported by the National Natural Science
Foundation of Liaoning Province (Grant No. 2019-ZD-0364).
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