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increase in the reactant concentration in the catalyst leads to an
enhancement of the activity,1 in good agreement with the
reactant enrichment in carbon nanotube catalysts.26
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It is also interesting to note that the ILs functionalized on the
PDVB-vim support showed very good recyclability (Table 1,
entries 10 and 11). For example, there was almost no activity
loss over PDVB-[C1vim][SO3CF3] after recycling four times
(entry 11). This might be associated with the stable polymer
network (Figure S9 and Table S2). In contrast, after the same
number of recycles, the activity over Amberlyst 15 was
remarkably reduced from 28.6 to 20.2% (entry 12; also see
Table S2). The excellent recyclability of the catalysts is
potentially important for industrial applications.
We extended the use of PDVB-[C1vim][SO3CF3] to the
Peckmann reaction (Table S3), the Kharasch addition (Table
S3), the esterification of cyclohexanol with acetic acid (Table
S4), and the hydration of propylene oxide (Table S4). The
results showed that the heterogeneous catalyst PDVB-[C1vim]-
[SO3CF3] is still much more active than the homogeneous
catalysts [C1vim][SO3CF3] and H2SO4 with the same number
of active sites (Table S3 and S4) as a result of the high
enrichment and good miscibility of the superhydrophobic
mesoporous polymers for the reactants (Figure S13 and Figure
S14).
In summary, ILs functionalized on superhydrophobic
mesoporous polymers, such as PDVB-[C1vim][SO3CF3],
were successfully prepared and found to exhibit even higher
activities in a series of catalytic reactions such as trans-
esterification, the Peckmann reaction, Kharasch addition,
esterification, and hydration than the corresponding homoge-
neous ILs. This feature should be important in the future for
the design and preparation of heterogeneous catalysts with both
high activity and good recyclability.
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ASSOCIATED CONTENT
* Supporting Information
Synthesis and characterization details. This material is available
■
(21) Liu, F. J.; Meng, X.-J.; Zhang, Y.-L.; Ren, L.-M.; Nawaz, F.; Xiao,
F.-S. J. Catal. 2010, 271, 52.
(22) Zhang, Y.-L.; Wang, J.-N.; He, Y.; He, Y.-Y.; Xu, B.-B.; Wei, S.;
Xiao, F.-S. Langmuir 2011, 27, 12585.
S
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2008, 112, 9443.
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Chem., Int. Ed. 2011, 50, 4913.
AUTHOR INFORMATION
Corresponding Author
■
Author Contributions
∥F.L. and L.W. contributed equally.
Notes
NOTE ADDED AFTER ASAP PUBLICATION
The authors declare no competing financial interest.
■
The structure of PDVB in Figure 1A was incomplete in the
version published ASAP September 28, 2012. The corrected
version was reposted on October 3, 2012.
ACKNOWLEDGMENTS
■
This work was supported by the State Basic Research Project of
China (2009CB623507) and the National Natural Science
Foundation of China (U1162201, 21273197, and 21203122).
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