HIPE Polymerization Materials Functionalized with Iodic-BODIPY on the Surface as Porous Heterogeneous Visible-Light Photocatalysts

Article abstract of DOI:10.1002/asia.201601628

A high internal phase emulsion polymerization (PolyHIPE) material, with iodine-functionalized boron-dipyrromethene (iodic-BODIPY) immobilized on its surface, composes a porous heterogeneous organic photocatalyst (iodic-BODIPY-PolyHIPE). It shows high catalytic efficiency on the selective oxidation reaction of aromatic sulfides under visible light. The substrates were almost fully converted to their corresponding sulfoxides and no sulfones were observed. Most importantly, iodic-BODIPY-PolyHIPE shows >1.6-fold reaction rate compared to the previous non-inorganic heterogeneous photocatalysts.

Full text of DOI:10.1002/asia.201601628

CHEMISTRY
AN ASIAN JOURNAL
www.chemasianj.org
Accepted Article
Title: HIPE polymerization materials functionalized with iodic-
BODIPY on the surface as porous heterogeneous visible-light
photocatalysts
Authors: Wenliang Li, Leijiao Li, Guihua Cui, Yu Bai, Xiao Xiao, Yuxin
Li, and Lesan Yan
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To be cited as: Chem. Asian J. 10.1002/asia.201601628
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HIPE Polymerization Materials Functionalized with Iodic-BODIPY
on the Surface as Porous Heterogeneous Visible-light
Photocatalysts
+
[a,d,e]
+ [c]
[a]
[a]
[a]
[d]
[b]
Wenliang Li ,
Leijiao Li , Guihua Cui* Yu Bai, Xiao Xiao, Yuxin Li, Lesan Yan*
Abstract: High internal phase emulsion polymerization (PolyHIPE)
styrylated active BODIPY moieties, styrene, and divinylbenzene
was used to develop another novel porous heterogeneous
material, with iodine-functionalized Boron-dipyrromethene (iodic-
[8]
BODIPY) immobilized on its surface, composes
a
porous
photocatalyst (Short for PHP5). The active photocatalysts were
chemically attached to the polystyrene backbone and were thus
available to the substrate molecules. This heterogeneous
photocatalyst showed high photocatalytic efficiency in the
oxidation of sulfides as well as high photostability under visible
light. However, the reaction rate (>60 hours to consume all the
thioanisole) was disappointing due to the heterogeneous nature
of the photocatalyst and the limited availability of the BODIPY
species on the surface.
heterogeneous organic photocatalyst (iodic-BODIPY-PolyHIPE). It
shows high catalytic efficiency on the selective oxidation reaction of
aromatic sulphides under visible light. Over 99% substrates were
converted to sulfoxide. No sulfones, the peroxidation products of
sulphides, were founded. Most importantly, iodic-BODIPY-PolyHIPE
shows > 1.6 fold reaction rate compared to the previous non-
inorganic heterogeneous photocatalysts.
BODIPY compounds have been recognized as a group of
outstanding dyes due to their excellent characteristics such as
high fluorescence quantum yields, large molar absorption
coefficients, and most importantly, excellent thermal and
Heterogeneous catalysis refers to a kind of catalysis in which the
phase of the catalyst differs from that of the reactants.
Heterogeneous catalysts are easily separated from the product
[1]
after the reaction. Many inorganic materials, such as silica gels,
[9]
photochemical stability both in solution and in solid states.
[2]
[3]
[4]
sepiolites, zeolites, carbon nanotubes, and mesoporous
Because of their impressive qualities, we have focused on
BODIPY-based photocatalysts and proved that BODIPYs are a
[5]
titanium dioxide have been used extensively as photocatalyst
supports. A big disadvantage of these materials, however, is that
for many inorganic supports there are no available functional
groups on the surface. Active catalysts are typically loaded by
physical adsorption, thus it is difficult to control the contents of
catalysts. Moreover, the catalyst may remain in the solution by
desorption, making the separation a big concern. To create new
high-porosity materials, a new method, HIPE polymerization, is
[10]
category of effective, alternative organic photocatalysts.
Recently, we reported for the first time that the use of iodine-
functionalized BODIPY achieved higher photocatalytic efficiency
and faster reaction rates (it is enough to complete the reaction in
3
(
hours) in the oxidation of sulfides under visible light
Supporting information, Figure S1), since fluorophores carrying
heavy atoms generally have high intersystem crossing quantum
yield (Φisc) and high singlet oxygen quantum yield (Φ ) due to
[6]
in development.
These porous materials are attractive
Δ
candidates as catalyst supports because of their unique tunable
[11]
the heavy atom effect. In the meantime, Zhao and co-works
produced iodo-BODIPY immobilized on porous silica as an
efficient photocatalyst for photoredox catalytic organic
[7]
architecture. In our previous work, HIPE polymerization of
[5b]
reaction. More recently, Patra’s group developed a series of
[
a]
W, Li, G, Cui, Y, Bai, X, Xiao
Jilin Medical University
Jilin Road. 5#, Jilin 132013 (China)
E-mail: cuiyuhan1981_0@sohu.com
L, Yan
porous organic polymers incorporating BODIPY moiety and
explored its application as photocatalyst on the oxidation
[12]
reaction of thioanisole within 24 h under visible light.
Liras’
[b]
group reported the synthesis of CMPBDP, a conjugated
microporous polymer based on halogen-free BODIPY moiety.
The material was used as heterogeneous photocatalyst for the
oxidation of thioanisole and it took 24 hours to completely
Department of Bioengineering
University of Pennsylvania
2
10 S. 33rd Street, Philadelphia, PA 19104-6321, United States.
E-mail: lesanyan@gmail.com
L, Li
[13]
[
c]
consume the substrate.
All of these results suggesting that
State Key Laboratory of Rare earth Resource Utilization
Changchun Institute of Applied Chemistry
Renmin Street. 5625#, Changchun 130022 (China)
W, Li, Y, Li
School of Life Science
Northeast Normal University
Jingyue Street. 2555#, Changchun 130024 (China)
W, Li
Key Laboratory of Preparation and Application of Environmental
Friendly Materials, Ministry of Education
Jilin Normal University
BODIPY based photocatalyst are useful on the oxidation of
sulphides, but the reaction rate is still far from our expectation.
In light of the above results, a novel porous heterogeneous
photocatalyst, iodic-BODIPY-PolyHIPE, as shown in Scheme 1,
was prepared by attaching the iodic-BODIPY moieties onto the
inner surface of the PolyHIPE porous matrix via the click
reaction. Iodic-BODIPY-PolyHIPE can work under visible-light
irradiation with high stability and excellent catalytic efficiency for
the selective oxidation reaction of sulfides. More importantly, to
the best of our knowledge, the reaction rate for sulfides selective
oxidation is the fastest compared to those of previously reported
non-inorganic heterogeneous materials.
[
d]
[
e]
Zhuoyue Street. 399#, Changchun 130103 (China)
These authors contributed equally to this work.
[
+]
Supporting information for this article is given via a link at the end of
the document.
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COMMUNICATION
Figure 1. Photographs of iodic-BODIPY-PolyHIPE. (A) Photograph in dry solid
state under typical ambient light. (B) Fluorescence emission photograph in
solid state excited with a 6 W UV lamp (λex = 365 nm).
Scheme 1. Iodic-BODIPY-PolyHIPE and its application in photocatalyzed
sulfide oxidation.
Fig. 2A shows typical SEM image of iodic-BODIPY-
PolyHIPE, revealing its interconnected porous structure. It is full
of fairly large cavities separated by thin walls. There are many
small holes in the walls to promote interconnection between
adjacent cavities. The big cavities correspond to the inner
aqueous phase and the walls correspond to the continuous
phase before HIPE polymerization. Formation of these small
The HIPE polymerization procedure used to obtain highly
[8]
porous materials was adopted from our previous report. The
organic phase consisted of vinylbenzyl chloride, styrene, and
divinylbenzene. The Span 80 was added to the organic phase
(
0.3 mL/mL) as a surfactant for emulsion formation. The inner
phase was an aqueous solution of CaCl (~1 wt%) and K
~0.2 wt%). Its volume percent was 90% in the emulsion system.
After HIPE polymerization, Cl-PolyHIPE, highly tough
monolithic material was obtained. Azide functioned N -PolyHIPE
was prepared from the reaction of Cl-PolyHIPE and sodium
azide. To conjugate with N -PolyHIPE, iodic-BODIPY, an active
2
2 2 8
S O
(
holes is due to volume contraction of the cavity walls during
a
[15]
polymerization and subsequent solvent extraction.
The
3
biggest cavities have a diameter of ca. 9 μm while the
interconnecting pores are ca. 1.3 μm in diameter. The average
cavity size of iodic-BODIPY-PolyHIPE is ca. 4.5 μm in diameter
3
moiety with an alkyne group and two iodine atoms was
synthesised as previously described (Figure S2 in supporting
2 -1
(
Figure 2B) and the surface area is 230 m g , as measured by
mercury intrusion porosimetry. Thus, the porosity was calculated
to be 77%, which is a little lower than what we estimated (~90%,
as mentioned above). This is likely due to the damage of the
emulsion during polymerization process or the collapse of HIPE
architecture during the reaction process of attaching the iodic-
BODIPY dyes.
[14]
information).
Finally, iodic-BODIPY-PolyHIPE,
a porous
heterogeneous organic photocatalyst with iodic-BODIPY
moieties on the surface, was prepared by “click” reaction
between N -PolyHIPE and iodic-BODIPY (Scheme 2). Since
3
HIPE material has been proved to be an effective catalyst
surpport, and iodine functionalized BODIPY has been
recognized as a better photocatalyst with higher singlet oxygen
generation quantum yields than halogen-free BODIPY, the iodic-
BODIPY-PolyHIPE, should be no doubt an excellent
heterogeneous photocatalyst by combining both of the
advantages.
Figure 2. (A) Typical SEM image of iodic-BODIPY-PolyHIPE. (B) Pore size
distribution of iodic-BODIPY-PolyHIPE measured by mercury intrusion
porosimetry.
The UV-visible diffuse reflectance spectra (DRS) showed
that iodic-BODIPY-PolyHIPE and iodic-BODIPY have similar
absorption (Fig. 3A), confirming the presence of iodic-BODIPY
moieties on the surface of PolyHIPE material. In the FTIR
-
1
spectrum (Fig. 3B), the νN3 bands at 2100 cm are greatly
weakened after the “click” reaction, demonstrating that the azide
groups were consumed. All the above results indicated that
iodic-BODIPY moieties were successfully attached to the
surface of PolyHIPE materials, and provided convincing
evidences for the potential photoactivity of iodic-BODIPY-
PolyHIPE in the solid state.
Scheme 2. Preparation of iodic-BODIPY-PolyHIPE.
As shown in Fig. 1A, iodic-BODIPY-PolyHIPE is in the form
of dark red powder. It exhibits a bright red fluorescence emission
excited with a 6 W UV lamp (λex = 365 nm, Fig. 1B).
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COMMUNICATION
[
a]
Table 1. Photocatalytic oxidation of sulfides.
vsible light
photocatalyst
O
S
R1
S
R1
Ar
Ar
methanol, in air
[b]
Conversion (%)
Entry
Ar
R
1
iodic-BODIPY-
PolyHIPE/15 h
PHP5/60 h
1
2
3
4
5
Ph
4-MeC
H
H
H
H
Me
>99
91
>99
81
>99
92
92
55
77
6 4
H
4-ClC
2-ClC
6
H
H
4
Figure 3 (A) UV-vis DRS spectra of iodic-BODIPY-PolyHIPE, iodic-BODIPY
and N3-PolyHIPE. (B) FTIR spectra of iodic-BODIPY-PolyHIPE and N3-
PolyHIPE.
6
4
Ph
60
[
a] All the reactions were run at room temperature. [b] Conversions were
1
determined by H NMR.
The iodic-BODIPY content on the surface of iodic-BODIPY-
PolyHIPE was determined by elemental analysis (CHN). The
nitrogen contents of N -PolyHIPE and iodic-BODIPY-PolyHIPE
3
are 5.69 wt% and 4.64 wt%, respectively. According to its
molecular formula, the nitrogen content in iodic-BODIPY is 4.45
wt%. Thus, the iodic-BODIPY content in PolyHIPE material was
calculated to be 15.32% (w/w).
To give a perspective view on the reaction efficiency and
the reaction rate of the iodic-BODIPY-PolyHIPE catalyst, a
comparative study with the catalysts developed in Zhang’s group
(
2
B-(Boc-CB) -BT) and our group (PHP5) has been summarized
in Table 2. PhBDP-2I, a small molecular BODIPY dye, shows
the highest reaction rate. It took only 3 h to complete the
reaction with all of thioanisole converted to methyl phenyl
sulfoxide (Entry 1, Table 2). In contrast, PhBDP, another small
molecular BODIPY dye without iodine atoms, took 24 h to
achieve the same effect (Entry 2, Table 2). Within the same time
This active iodic-BODIPY content is much higher than that
of our previously prepared PHP5 (6.5 wt% in halogen-free
[8]
BODIPY). In addition, the iodic-BODIPY was immobilized on
the surface of PolyHIPE materials, not distributed in the skeleton
of HIPE materials as PHP5 did. Therefore, we are convinced
that iodic-BODIPY-HIPE will give better performance in
photocatalyzed oxidation reaction.
(3 h), only 33% of thioanisole was converted to methyl phenyl
sulfoxide with iodic-BODIPY-PolyHIPE as the catalyst (Figure 1).
It is reasonable that the reaction rate with iodic-BODIPY-
PolyHIPE is slower than that with PhBDP-2I due to the
heterogeneity in the case of iodic-BODIPY-PolyHIPE. However,
iodic-BODIPY-PolyHIPE showed the fastest reaction rate in all
of the heterogeneous catalysts. Reaction with 0.5 mol % of
iodic-BODIPY-PolyHIPE photocatalyst in methanol yields more
than 99% of product after 15 h (entry 3, Table 2), which is 4-fold
faster than PHP5 in the same reaction conditions (entry4, Table
To assess the photo-catalysis capability of iodic-BODIPY-
PolyHIPE, the photocatalyzed sulfide oxidation reaction was
performed in freshly distilled methanol at room temperature with
no additives. The sulfide concentration was about 3.2% (v/v).
Iodic-BODIPY-PolyHIPE was pulverized to a size of ca. 1 mm
and was suspended in methanol at a concentration of ca. 5.6
mg/mL under stirring. A 24 W household fluorescent lamp with a
highpass filter (λ = 395 nm) was used as the visible light source
2) and 1.6-fold faster than B-(Boc-CB)
2
-BT (entry 5, Table 2),
respectively.
(400 ~ 700 nm).
Figure 4 shows the kinetic processes for iodic-BODIPY-
Table 2. Photocatalytic oxidation of thioanisole at room temperature.
PolyHIPE catalyzed sulfide oxidation reaction. It took only 15 h
for all the thioanisoles to be converted into methyl phenyl
sulfoxides. No sulfone was detected, suggesting the high
selectivity of this reaction. We have also expanded the scope of
substrates for the reaction under the catalysis of iodic-BODIPY-
PolyHIPE in 15 h (Table 1, entries 2-5). Compared to PHP5 in
Conversion
Time
(h)
Entry
Catalyst
a
(
%)
b[11]
1
2
3
4
5
PhBDP-2I
PhBDP
>99
>99
>99
>99
99
3
60 h, iodic-BODIPY-PolyHIPE showed a faster reaction rate and
b[11]
24
15
60
24
higher conversion in general.
iodic-BODIPY-PolyHIPE
b[8]
PHP5
b[16]
2
B-(Boc-CB) -BT
1
[
a] Conversions were determined by H NMR. [b] The compounds have been
named as published papers.
The recyclability of iodic-BODIPY-PolyHIPE was measured
by thioanisole oxidation reaction driven by visible light. The
photocatalytic activity can be maintained within 30 hours. After
that, the conversion went down dramatically (Supporting
information, Figure S8) as a result of the collapse of PolyHIPE
architecture and/or the photobleaching of BODIPY dyes. To get
a better understanding of the photocatalytic nature in the
Figure 4. The conversion of thioanisole as
a function of reaction time
photocatalyzed by the iodic-BODIPY-PolyHIPE under visible light from a 24 W
fluorescent lamp.
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photocatalytic oxidation reaction of thioanisole, a series of
control experiments were carried out. The reaction showed no
conversion of the thioanisole, either in the absence of iodic-
BODIPY-PolyHIPE or in the dark (Supporting information, table
S2, entries 1 and 2). Moreover, only 2% thioanisole was
converted to methyl phenyl sulfoxide when the reaction was
3
In a 100 mL round bottomed flask were added N -PolyHIPE (100 mg),
iodic-BODIPY (82 mg, 0.13 mmol), sodium ascorbate (52 mg, 0.26 mmol)
and dissolved in dry DMF (40 mL). The solution was purged with argon
for 15 min. To the mixture was then added CuCl (9.9 mg, 0.1 mmol) and
o
the reaction mixture was stirred under argon atmosphere at 70 C for 12
h. After completion of the reaction, the solid product was filtered and
washed with hot water and ethanol to remove the unreacted iodic-
BODIPY. Iodic-BODIPY-PolyHIPE was obtained as a dark red porous
material.
2
carried out under N protection (Table S2, entry 3 in supporting
information). In addition, the evolution of a middle reaction was
also monitored (Supporting information, Figure S9). The catalyst
was removed at 7.5 h and the reaction was performed without
catalyst for 5 hours. During this period, there was no increase in
conversion of thioanisole. After that, iodic-BODIPY-PolyHIPE
was re-added and irritated with visible light for another 7.5 h. At
the end of the reaction, all the substrates were consumed.
These results revealed that illumination, photocatalyst, and
oxygen are essential for this reaction to take place.
Sulfide oxidation catalyzed by iodic-BODIPY-PolyHIPE
Take oxidation of thioanisole as an example: To a flame-dried 10 mL
vial equipped with a magnetic stir bar were added iodic-BODIPY-
PolyHIPE (10.28 mg, containing iodic-BODIPY 2.5 mol, 0.005 equiv)
catalyst, thioanisole (62 µL, 0.5 mmol, 1.0 equiv), and dried methanol
(
=
0.5 mL). A 24 W household fluorescent light bulb with a highpass filter (λ
395 nm) was used as the visible light source. The reaction mixture was
In summary, iodic-BODIPY photocatalysts were immobilized
on the surface of PolyHIPE materials by click chemistry. The
porous heterogeneous photocatalyst, iodic-BODIPY-HIPE,
demonstrated high photocatalytic activity, excellent selectivity
and a reaction rate at least > 1.6 times faster than other organic
heterogeneous photocatalysts in sulfide oxidation reaction. This
simple strategy could open the door for designing new HIPE-
based porous heterogeneous catalysts to increase reaction
rates and will bring benefits to the future catalytic industry.
stirred at room temperature in air at a distance of ca. 5 cm from the lamp
(the irradiance is about 17.5 W/m for the distance). After the reaction
2
was completed, the iodic-BODIPY-PolyHIPE was then removed by
centrifugation and the supernatant was collected. The reaction mixture
1
was subjected to H NMR test, and the integrated area ratio between the
1
H NMR peaks of the substrate and product was used to calculate the
conversion yields.
Acknowledgements
We give our sincere thanks to Lillian M. Eisner from Department
of Chemistry at the Dartmouth College for editing the manuscript.
We acknowledge the financial support from the National Natural
Science Foundation of China (Nos. 51403031, 51402286), from
the Jilin province education department (No. 2015394), from the
Youth Foundation project of Jilin province health and family
planning commission (No. 2014Q049, 2016Q053), from the Jilin
city science & technology innovation and development projects
Experimental Section
Preparation of Cl-PolyHIPE
To prepare Cl-PolyHIPE by HIPE polymerization, the following steps
were performed: (1) Preparation of the organic phase: In a three-necked
round bottomed flask equipped with a mechanical stirrer and a dropping
funnel, followed by addition of vinylbenzyl chloride (4.75 mL), styrene
(
4.75 mL), divinylbenzene (0.5 mL) and span 80 (3.0 mL). The solution
(Nos. 20166032, 20166033), and the Open Project Program of
was stirred at 400 rpm and purged with argon for 20 min at room
temperature; (2) Preparation of the high internal phase emulsion:
potassium persulfate (0.2 g) and calcium chloride (1.0 g) were dissolved
in 90 mL water, which was purged with argon for 20 min. The volume
ratio of the aqueous phase to organic phase was 9 : 1. The aqueous
phase was placed in the dropping funnel and added dropwise to the
organic phase. After complete addition of the
solution, the emulsion was kept stirring for additional
Polymerization of the emulsion: After stirring, the emulsion was
immediately transferred into a polyethylene bottle, the neck of the bottle
was covered with a polyethylene film to reduce evaporative losses. The
bottle was placed in an oven at 60 C for 24 h. (4) Washing the reaction
product: After this period the polyethylene bottle was cut away from the
reaction product. The product was then exhaustively extracted with hot
ethanol to remove the water and residual organic compounds.
the product was dried under vacuum at room temperature to give Cl-
PolyHIPE as a white monolithic material.
Key Laboratory of Preparation and Application of
Environmentally Friendly Materials (Jilin Normal University),
Ministry of Education, China (No. 2017006).
Keywords: HIPE polymerization • iodic-BODIPY •
heterogeneous materials • photocatalysts • the oxidation of
sulfides
K
2
S
2
O
8
/CaCl
2
/water
5
min; (3)
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bottomed flask. Sodium azide (1.0 g, 15.1 mmol) was added to the
solution. Then, the mixtures were stirred at 80 C overnight. After that,
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Chemistry - An Asian Journal
10.1002/asia.201601628
COMMUNICATION
Entry for the Table of Contents
COMMUNICATION
Wenliang Li, Leijiao Li, Guihua Cui*, Yu
Bai, Xiao Xiao, Yuxin Li, Lesan Yan*
Page No. – Page No.
HIPE
Polymerization
Materials
Functionalized with Iodic-BODIPY on
the
Surface
as
Porous
Visible-light
A
novel porous heterogeneous photocatalyst, prepared from the surface
Heterogeneous
Photocatalysts
functionalization of high internal phase emulsion polymerization (PolyHIPE)
materials, demonstrated high photocatalytic activity, excellent selectivity and fast
reaction rate.
For internal use, please do not delete. Submitted_Manuscript
This article is protected by copyright. All rights reserved.