Chemistry - A European Journal
10.1002/chem.202002150
RESEARCH ARTICLE
after 6 h reaction was achieved over 5 cycles (Figure S19), with a
small drop in aldehyde selectivity (Figure S19 and Table 1). Rh
contents in the liquid products, analyzed by the inductively
coupled plasma optical emission spectroscopy (ICP-OES),
indicate that there is no leaching of Rh active metal species. The
limited decrease of the TOF for the 6th recycled Rh-P-COF-1 (ca.
[6]
a) Q. Sun, Y. Tang, B. Aguila, S. Wang, F.-S. Xiao, P. K. Thallapally, A.
M. Al-Enizi, A. Nafady, S. Ma, Angew. Chem. Int. Ed., 2019, 58, 8670-
8675; b) S.-Y. Ding, J. Gao, Q. Wang, Y. Zhang, W.-G. Song, C.-Y. Su,
W. Wang, J. Am. Chem. Soc. 2011, 133, 19816-19822. c) Q. Fang, S.
Gu, J. Zheng, Z. Zhuang, S. Qiu, Y. Yan, Angew. Chem. Int. Ed., 2014,
53, 2878-2882.
[
[
[
[
[
7]
8]
9]
A. P. Côté, A. I. Benin, N. W. Ockwig, M. Keeffe, A. J. Matzger, O. M.
Yaghi, Science 2005, 310, 1166.
6.2 %) and Rh-P-COF-2 (ca. 1.2 %) compared to the
corresponding fresh Rh-P-COFs (Table 1) indicates an excellent
reusability of the Rh-P-COFs catalysts.
Y. Lan, X. Han, M. Tong, H. Huang, Q. Yang, D. Liu, X. Zhao, C. Zhong,
Nat. Commun. 2018, 9, 5274.
K. Kamiya, R. Kamai, K. Hashimoto, S. Nakanishi, Nat. Commun. 2014,
5
, 5040.
10] G. Lin, H. Ding, R. Chen, Z. Peng, B. Wang, C. Wang, J. Am. Chem. Soc.
017, 139, 8705-8709.
Conclusion
2
11] L.-H. Li, X.-L. Feng, X.-H. Cui, Y.-X. Ma, S.-Y. Ding, W. Wang, J. Am.
Chem. Soc. 2017, 139, 6042-6045.
In summary, we have demonstrated the synthesis of two
examples of high crystalline and porous triphenylphosphine-
based covalent organic framework (P-COFs) through a Schiff
base reaction. Both P-COF-1 and P-COF-2 adopt an AA-stacking
to form accessible open channels of 37 Å and 46 Å, respectively.
[12]
H. Guo, Y. C. Fan, Z. Sun, Y. Wu, O. Kwon, Chem. Rev. 2018, 118,
0049-10293.
13] M. Zhang, Y. Li, C. Bai, X. Guo, J. Han, S. Hu, H. Jiang, W. Tan, S. Li, L.
1
[
[
Ma, ACS Appl. Mater. Inter. 2018, 10, 28936-28947.
14] P. J. C. Hausoul, T. M. Eggenhuisen, D. Nand, M. Baldus, B. M.
Weckhuysen, R. J. M. Klein Gebbink, P. C. A. Bruijnincx, Catal. Sci.
Technol. 2013, 3, 2571-2579.
2
The P-COFs supported Rh(CO) (acac) catalysts (Rh-P-COFs) via
-1
Rh-P coordination bonds show high TOF (> 2000 h ) , high
[
[
15] S. Ravi, P. Puthiaraj, K. Yu, W.-S. Ahn, ACS Appl. Mater. Inter. 2019, 11,
aldehyde selectivity (ca. 99 %) and excellent catalyst reusability
11488-11497.
(
> 5 cycles) for hydroformylation of olefins. We believe that the
16] J. Huang, J. Tarábek, R. Kulkarni, C. Wang, M. Dračínský, G. J. Smales,
Y. Tian, S. Ren, B. R. Pauw, U. Resch-Genger, M. J. Bojdys, Chem. –
Eur. J. 2019, 25 (53), 12342-12348.
novel triphenyl phosphine-based COFs are not only suitable to
immobilize homogeneous metal-based catalysts but also have
the important potential applications in other fields such as
adsorption-separation, electrocatalysis and photocatalysis.
[17] Y. L. Zhu, S. Wan, Y. H. Jin, W. Zhang, J. Am. Chem. Soc. 2015, 137,
3772-13775.
1
[
18] a) Q. Sun, Z. F. Dai, X. L. Liu, N. Sheng, F. Deng, X. J. Meng, F. S. Xiao,
J. Am. Chem. Soc. 2015, 137, 5204-5209; b) K. Dong, Q. Sun, Y. Q.
Tang, C. Shan, B. Aguila, S. Wang, X. J. Meng, S. Q. Ma, F. S. Xiao, Nat.
Commun. 2019, 10.
Acknowledgements
[
[
[
[
19] Tao, R., Shen, X. R., Hu, Y. M., Kang, K., Zheng, Y. Q., Luo, S. C., Yang,
S. Y., Li, W. L., Lu, S. L., Jin, Y. H., Qiu, L., Zhang, W., Small 2020,
doi:10.1002/smll.201906005.
Y. Liu and Y. Fan thank National Natural Science Foundation of
China (NSFC), S. He and H.J. Heeres thank Netherlands
Organization for Scientific Research (NWO) for their financial
support (NSFC Grant No. 21773107 and NWO-LIFT Programme
Grant No.731.016.401) to this work.
20] a) H. Guo, Y. C. Fan, Z. Sun, Y. Wu, O. Kwon, Chem. Rev. 2018, 118,
10049-10293; b) R. Franke, D. Selent, A. Borner, Chem. Rev. 2012, 112,
5675-5732.
21] a) H. Nishi, T. Namari, S. Kobatake, J. Mater. Chem. 2011, 21, 17249-
7258; b) F. Chalier, Y. Berchadsky, J.-P. Finet, G. Gronchi, S. Marque,
1
P. Tordo, J. Phys. Chem. 1996, 100, 4323-4330.
Keywords: covalent organic frameworks • triphenylphosphine •
olefin hydroformylation • recyclable heterogeneous catalyst
22] a) P. J. Waller, Y. S. AlFaraj, C. S. Diercks, N. N. Jarenwattananon, O.
M. Yaghi, J. Am. Chem. Soc. 2018, 140, 9099-9103; b) G. Zhang, M.
Tsujimoto, D. Packwood, N. T. Duong, Y. Nishiyama, K. Kadota, S.
Kitagawa, S. Horike, J. Am. Chem. Soc. 2018, 140, 2602-2609.
23] C. Qian, S.-Q. Xu, G.-F. Jiang, T.-G. Zhan, X. Zhao, Chem. - Eur. J. 2016,
[
1]
a) N. Huang, P. Wang, D. Jiang, Nat. Rev. Mater. 2016, 1; b) F. Beuerle,
B. Gole, Angew. Chem. Int. Ed., 2018, 57, 4850-4878; c) D. Jiang, X.
Chen, K. Geng, R. Liu, K. T. Tan, Y. Gong, Z. Li, S. Tao, Q. Jiang, Angew.
Chem. Int. Ed., 2020, doi:10.1002/anie.201904291.
[
[
2
2, 17784-17789.
24] a) X. Wang, X. Han, J. Zhang, X. Wu, Y. Liu, Y. Cui, J. Am. Chem. Soc.
016, 138, 12332-12335; b) G. Lin, H. Ding, D. Yuan, B. Wang, C. Wang,
[
[
[
2]
3]
4]
a) H. Fan, A. Mundstock, A. Feldhoff, A. Knebel, J. Gu, H. Meng, J. Caro,
J. Am. Chem. Soc. 2018, 140, 10094-10098; b) P. Wang, X. Chen, Q.
Jiang, M. Addicoat, N. Huang, S. Dalapati, T. Heine, F. Huo, D. Jiang,
Angew. Chem. Int. Ed., 2019, 58, 15922-15927.
2
J. Am. Chem. Soc. 2016, 138, 3302-3305.
[
[
[
[
[
25] S. Karak, S. Kandambeth, B. P. Biswal, H. S. Sasmal, S. Kumar, P.
Pachfule, R. Banerjee, J. Am. Chem. Soc. 2017, 139, 1856-1862.
26] K. S. W. Sing, D. H. Everett, R. A. W. Haul, L. Moscou, R. A. Pierotti, J.
Rouquerol, T. Siemieniewska, Pure Appl. Chem. 1985, 57, 603-619.
27] F. J. Uribe-Romo, J. R. Hunt, H. Furukawa, C. Klock, M. O'Keeffe, O. M.
Yaghi, J. Am. Chem. Soc. 2009, 131, 4570-4571.
a) Z. Li, N. Huang, K. H. Lee, Y. Feng, S. Tao, Q. Jiang, Y. Nagao, S.
Irle, D. Jiang, J. Am. Chem. Soc. 2018, 140, 12374-12377; b) H. Singh,
V. K. Tomer, N. Jena, I. Bala, N. Sharma, D. Nepak, A. De Sarkar, K.
Kailasam, S. K. Pal, J. Mater. Chem. A. 2017, 5, 21820-21827.
a) J. Thote, H. B. Aiyappa, A. Deshpande, D. Diaz Diaz, S. Kurungot, R.
Banerjee, Chem. - Eur. J. 2014, 20, 15961-15965; b) V. S. Vyas, F.
Haase, L. Stegbauer, G. Savasci, F. Podjaski, C. Ochsenfeld, B. V.
Lotsch, Nat. Commun. 2015, 6, 8508; c) J. Lv, Y.-X. Tan, J. Xie, R. Yang,
M. Yu, S. Sun, M.-D. Li, D. Yuan, Y. Wang, Angew. Chem. Int. Ed., 2018,
28] Q. Liao, C. Ke, X. Huang, G. Zhang, Q. Zhang, Z. Zhang, Y. Zhang, Y.
Liu, F. Ning, K. Xi, J. Mater. Chem. A 2019, 7 (32), 18959-18970.
29] a) S. Kandambeth, A. Mallick, B. Lukose, M. V. Mane, T. Heine, R.
Banerjee, J. Am. Chem. Soc. 2012, 134, 19524-19527; b) X. Han, Q. Xia,
J. Huang, Y. Liu, C. Tan, Y. Cui, J. Am. Chem. Soc. 2017, 139, 8693-
5
7, 12716-12720.
a) Q. Xu, S. Tao, Q. Jiang, D. Jiang, J. Am. Chem. Soc. 2018, 140, 7429-
432; b) H. Xu, S. Tao, D. Jiang, Nat. Mater. 2016, 15, 722.
8
697.
30] J. Zhang, M. Poliakoff, M. W. George, Organometallics 2003, 22, 1612-
618.
[
5]
[
7
1
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