A diiodo-BODIPY postmodified metal-organic framework for efficient heterogeneous organo-photocatalysis

Article abstract of DOI:10.1039/c6ra03516g

The organic photosensitizer diiodo-BODIPY has been covalently conjugated into a Zr(iv)-based metal-organic framework with UiO topology via postsynthetic modification, which serves as a highly active and recyclable heterogeneous photocatalyst for aerobic c

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A diiodo-BODIPY postmodified metal-organic framework for
efficient heterogeneous organo-photocatalysis†
Ying Quan,a Qiu-Yan Li,*a Quan Zhang,b Wen-Qiang Zhang,a Han Lu,a Jun-Hao Yu,a Jian Chen,a
Xinsheng Zhao*c and Xiao-Jun Wang*a
Received 00th January 20xx,
Accepted 00th January 20xx
DOI: 10.1039/x0xx00000x
www.rsc.org/
Organic photosensitizer diiodo-BODIPY has been covalently
Among these materials, MOFs as platforms for immobilizing
conjugated to a Zr(IV)-based metal-organic framework with UiO catalysts are very attractive because of their highly tunable
topology via postsynthetic modification, which serves as a highly nature.8 Especially, the postsynthetic modification (PSM)
active and recyclable heterogeneous photocatalyst for aerobic strategy allows various functional groups to be readily tagged
cross dehydrogenative coupling and oxidation/[3+2] cycloaddition into MOFs.9 However, there are limited examples of MOFs
reactions under visible light irradiation.
with attached photosensitizers for photocatalytic organic
transformations.7,10 Thus, it is urgent to develop an effective
and versatile method for introducing photocatalysts into MOFs,
with a purpose of achieving highly active heterogeneous
photo-catalysis. Thanks to their modular nature, it is readily
easy to prepare MOFs with tagged reactive groups, such as
amine and azide. This could provide many possibilities for
incorporation of a photosensitizer into MOFs through various
reactions, particularly for an organic photosensitizer. However,
there are few examples in this regard.
In the past several years, visible light mediated photoredox
catalysis has received a considerable attention, on account of
the green and sustainable method for a variety of organic
transformations under milder reaction conditions.1,2 Moreover,
it can generate some sophisticated molecules that are not
easily accessible by conventional thermal reactions. Typically,
the photoredox catalysts include noble metal Ru, Ir and Pt
complexes,1,3 as well as some of organic dyes,4 such as eosin Y
and Rose Bengal. As most of the reactions were performed
homogenously, therefore, it is difficult to recycle the catalysts
for reuse. Clearly, a straightforward solution for this challenge
is the immobilization of photo-catalysts into insoluble solid-
state materials, resulting in a heterogenous catalyst. In this
regard, several types of materials, such as silicas,5 polymers,6
and metal-organic frameworks (MOFs),7 have been employed
to achieve this purpose. For example, Zhao’s group has
successfully incorporated [Ru(bpy)3]2+ (bpy = 2,2’-bipyridine)
into organosilica for three photocatalytic transformations.5a
Cooper and coworkers prepared Rose Bengal conjugated
microporous polymers for aza-Henry reactions.6c Yu and Cohen
reported a Zr-based MOF UiO-67 decorating with [Ru(bpy)3]2+
for aerobic oxidation of arylboronic acids under visible light
irradiation.7b
UiO series of MOFs comprised of Zr6-cluster secondary
building units and dicarboxylate linkers represent a very rare
kind of highly stable and porous MOF materials.11 In this work,
we chose the amine-tagged UiO-68 (Zr-MOF UiO-68-NH2)
because of its large cavities.11 Then, an already established
organic photocatalyst diiodo-BODIPY12 was covalently
conjugated to the above Zr-MOF (Fig. 1). Herein, we reported
the example to validate the power of PSM for immobilizing
photosensitizers within MOFs, which results in a highly active
and recyclable heterogeneous photocatalyst for various
organic transformations under visible light.
Fig. 1 Schematic representation of preparation for UiO-68-BP. Inset: the photographs of
UiO-68-NH2 (left) and UiO-68-BP (right) under ambient light.
The amine-tagged Zr-MOF UiO-68-NH2 can be prepared in a
large scale by our modified literature method.13 A N,N’-
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dimethylformamide (DMF) solution of aminotriphenyldicar- products in good to excellent yields (Table 2, 3a-3g). Moreover,
boxylic acid (amino-TPDC) and ZrCl4 in the presence of HAc and the utilization of other nucleophiles, including nitroethane,
water was heated to 100 oC for 2 days, giving the desired nitropropane and dialkyl malonates, was also able to yield the
MOFs (for detail see ESI). As expected, powder X-ray desired products smoothly (Table 2, 3h-3l and Table S1 in ESI).
diffraction (XRD) of as-synthesized products is similar to the
Table 1 Screening of the reaction conditionsa
simulated pattern from its single-crystal structure,14
confirming the phase purity and UiO structural framework.
Scanning electron microscopy (SEM) image reveals their
hexagonal plate-like morphologies with diameter at ~100 nm
and thickness at
∼30 nm (Fig. 2a). Photocatalyst diiodo-
BODIPY was covalently incorporated into UiO-68-NH2 by the
mild reaction between acyl chloride activated carboxylic group
of organic species and amino group of bridging ligand,
affording a deeply red solid UiO-68-BP (Fig. 1 and ESI for detail).
Moreover, the post-modified UiO-68-BP still retained the
original hexagonal plate-like morphologies and powder XRD
pattern of its parent MOF (Fig. 2b and 2d).
Entry
1
Conditions
Time (h)
Yieldb(%)
72
UiO-68-BP (1 mg)
UiO-68-BP (1 mg)
UiO-68-BP (2 mg)
UiO-68-BP (2 mg)
UiO-68-BP (5 mg)
UiO-68-BP’ (2 mg)
UiO-68-BP” (2 mg)
UiO-68-NH2 (5mg)
No catalyst
2
3
2
3
3
3
3
3
3
-
2
79
3
76
4
88
5
89
6c
7c
8d
9
61
77
trace
trace
n.r.
n.r.
10e
11f
No light
No O2
3
aReaction conditions: 1a (0.1 mmol) and 2a (1.0 mL), green LEDs (λ = 520-530 nm,
3W). The reaction was conducted in an air atmosphere at room temperature.
1
c
bYields were determined by H NMR spectroscopy. n.r. = no reaction. UiO-68-
BP’ and UiO-68-BP” refer to ~2% and ~7% of organic linkers in MOF was
functionalized by diiodo-BODIPY, respectively. dThe reaction was performed in
the presence of UiO-68-NH2.eThe reaction mixture was stirred for 6 hours in the
dark. fDegassed by nitrogen before irradiation.
Table
2 Aerobic CDC reactions of tetrahydroisoquinolines 1 with nitroalkan-es 2
catalyzed by UiO-68-BPa
Fig. 2 Typical SEM images for UiO-68-NH2 (a), UiO-68-BP (fresh, b) and UiO-68-BP after
catalysis (c); (d) Powder XRD patterns for UiO-68-NH2 and UiO-68-BP. Scale bar: 100 nm.
To verify that the immobilized diiodo-BODIPY in MOFs can
still work as an effective photoredox catalyst, the aerobic cross
dehydrogenative coupling (CDC) reaction of N-phenyl-1,2,3,4-
N
N
N
O2N
O2N
O2N
O2N
O2N
3c:
87%
F
tetrahydroisoquinoline
(
1a)
with nitromethane
(
2a
)
in
3a:
3b:
89%
88%
N
presence of air was performed as a model (Table 1). To our
delight, the mixture of 1a and 2a containing catalytic amount
UiO-68-BP under the irradiation of green LEDs (λmax = 520-530
nm) at room temperature for several hours, the formation of
the desired cross-coupling product 3a was observed in a
satisfied yield (Table 1, entry 1-4). No significant improvement
could be detected with increase of catalyst amount (Table 1,
entry 5). Other samples with lower loading amount of diiodo-
BODIPY exhibited lower catalytic activities (Table 1, entry 6-7).
Control experiments demonstrated that each component of
the reaction is critical to the reaction efficiency (Table 1, entry
8-12).
N
N
O2N
Cl
Br
O2N
OCH3
3d: 88%
3e: 87%
3f: 90%
OCH3
N
N
N
O2N
3g:
O2N
3h:
3i:
89%
N
85% (1:1.6)
82% (1:1.5)
N
N
O2N
3j:
Br
NO2
3k:
NO2
3l:
81% (1:1.6)
82% (1:1.5)
79% (1:1.5)
With this initial success, we subsequently screened the
reaction scope (Table 2 and S1 in ESI). Various substituted
1,2,3,4-tetrahydroisoquinoline derivatives can undergo the
CDC reaction with nitromethane efficiently, giving the
aReaction conditions: 1 (0.1 mmol), 2 (1 mL) and UiO-68-BP (2 mg) under air at
room temperature, and the irradiation time was 3 h. Yields were determined by
1H NMR. Ratios of the two diastereoisomers are given in parentheses.
2 | J. Name., 2012, 00, 1-3
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Meanwhile, the recyclability of UiO-68-BP as a hetero- similar and plausible mechanism was proposed in Scheme S3
geneous catalyst was also investigated, which can be readily (in ESI).2e,2f,4e Thus, these results confirmed that there still was
recovered from the reaction system by simple centrifugation. the efficient SET process between the immobilized
It was reused three photocatalysis recycles without obvious photocatalyst and substrate molecules.
loss of catalytic activity (88%, 78% and 72%, respectively). The
Table
3
Oxidation-[3+2] cycloaddition-aromatization tandem reaction of
6
with 7
little decrease of yield should be attributed some minor
decompositions of the organic photosensitizer diiodo-BODIPY
caused by the long irradiation. However, SEM and powder XRD
investigations of the recycled photocatalyst revealed that it
still maintain the crystalline structure and framework as well
as morphologies (Fig. 2c and 2d), mainly due to the highly
stable UiO frameworks.
catalyzed by UiO-68-BPa
EtO2C
N
EtO2C
O
EtO2C
N
O
N
O
N
N
N
F
O
O
O
8a: 88%
8b: 85%
8c: 80%
EtO2C
O
EtO2C
N
EtO2C
N
O
N
O
N
N
N
Cl
Br
OCH3
O
O
O
8d:
8e:
8f:
82%
75%
83%
EtO2C
N
EtO2C
N
EtO2C
N
O
N
O
N
O
N
Fig. 3 ESR measurements of a solution in CH3CN of UiO-68-BP without 1a in the
presence of DMPO (a) and TEMP (b) under the irradiation of green LEDs; a solution in
CH3CN of UiO-68-BP with 1a in the presence of TEMP (c) and DMPO (d) under the
irradiation of green LEDs.
O
O
O
F
8i:
80%
8g:
8h:
85%
81%
EtO2C
N
EtO2C
N
EtO2C
N
O
N
O
N
O
N
As previously reported, BODIPYs attached heavy atoms
serves as a good photosensitizer for producing singlet oxygen
(1O2), because of the enhanced intersystem crossing
capacity.15 However, it was recently proposed that the
superoxide radical anion (O2−•) act as the active species in
O
O
O
Cl
Br
OCH3
8j:
8k:
8l:
78%
81%
76%
photo-promoted aerobic CDC reactions.2e,2f,4e Thus, electron aReaction conditions: a 1 mL CH3CN solution of 6 (0.12 mmol), 7 (0.10 mmol) and
UiO-68-BP (2 mg) was irradiated for 2 hours under air at room temperature;
spin resonance (ESR) measurements were performed to make
then, NBS (0.12 mmol) was added into the reaction mixture, which was stirred for
further 10 min. Yields were determined by 1H NMR.
it clear, in which 2,2,6,6-tetramethyl-1-piperidine (TEMP) and
5,5-dimethyl-1-pyrroline-N-oxide (DMPO) were employed to
capture 1O2 and O2−•, respectively. As shown in Fig. 3, an
In order to further explore the applications of such
expected characteristic signal of 1O2 was observed upon
immobilized photocatalyst in MOFs, a series of oxidation-[3+2]
irradiation of the CH3CN mixture of UiO-68-BP and TEMP in air
cycloaddition-aromatization tandem reaction of
6 with 7
1
by green LEDs. However, the O2 signal could not be detected
catalyzed by UiO-68-BP was performed. As shown in Table 3,
most of the final pyrrolo[2,1-a]isoquinoline products were
obtained in satisfactory yields. Moreover, other organic
transformations mediated by oxygen, inculding aerobic amine
coupling and aerobic oxidation of arylboronic acid and
thioanisole, were also sucessfully and efficiently conducted in
the presence of UiO-68-BP, indicating its a wide range of
applications in organic photocatalysis (in ESI).
when 1a was added into the mixture. In contrast, there was no
signal when DMPO was added into the CH3CN mixture of UiO-
−•
68-BP, however, a characteristic signal of O2 trapped by
DMPO was clearly observed upon addition of 1a. These above
results indicate that although diiodo-BODIPY is a reported
efficient sensitizer in the production of 1O2,15 however, this
process is highly suppressed by the effective single electron
transfer (SET) between 1a and excited diiodo-BODIPY (PS*) in
the present case, along with the generation of the radical
cation 1a•+ and the radical anion PS−•. Subsequently, the
generated radical anion PS−• reacts with molecular oxygen to
produce the superoxide radical anion O2−•, which is a crucial
intermediate in the reaction. Based on the above analysis, a
Conclusions
In summary, we have reported an organic photosensitizer
diiodo-BODIPY postmodified metal-organic framework, which
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Acknowledgements
The work is financially supported from National Natural
Science Foundation of China (21302072, 51403081 and
21376113), Natural Science Foundation of Jiangsu Province
(BK20130226 and BK20140137) and the Priority Academic
Program Development of Jiangsu Higher Education Institutions
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A diiodo-BODIPY postmodified metal-organic framework for
efficient heterogeneous organo-photocatalysis
Ying Quan, Qiu-Yan Li, Quan Zhang, Wen-Qiang Zhang, Han Lu, Jun-Hao Yu, Jian Chen, Xinsheng
Zhao and Xiao-Jun Wang
A diiodo-BODIPY postmodified MOF acts as a highly active and recyclable heterogeneous
photocatalyst for aerobic CDC and oxidation/[3+2] cycloaddition reactions under visible light
irradiation.