SHEKARIZADEH AND AZADI
7 of 8
sublimed as described earlier to yield a colorless powder
over anhydrous Na2SO4, and the crude product was puri-
fied using column chromatography (n-hexane–ethyl ace-
tate). The evaporation of the solvent generated pure
desired products, all of which are known compounds
whose NMR spectra are in accordance with those
reported in the literature.[20–24]
(yield, 1.75 g; 85%). m.p. 206ꢀC (Janiak et al.[27]205–206-
1
ꢀC). H NMR (300 MHz, DMSO-d6): δ = 7.94 (d, 2H,
J = 2.8 Hz, H6, H60), 7.85 (d, 2H, J = 8.5 Hz, H3, H30),
6.90 (dd, 2H, J1 = 8.5 Hz, J2 = 2.5 Hz, H4, H40), 5.38
[s (br.), 4H, NH2]. 13C NMR (75 MHz, DMSO-d6):
δ = 147.3 (C2, C20), 145.3 (C5, C50), 135.7 (C6, C60), 124.2
(C3, C30), 121.8 (C4, C40).
ACKNOWLEDGMENT
We thank Shahid Chamran University of Ahvaz Research
Council, Ahvaz, for financial support of this study (Grant
Number 1398).
4.5 | Synthesis of GOFs
The GOF was prepared with the reaction between 5,50-
diamino-2,20-bipyridine and GO–COCl according to the
following procedure. At first, GO–COCl (0.1 g) was mixed
in dimethylformamide (DMF) (30 ml) and sonicated for
30 min. Then, 5,50-diamino-2,20-bipyridine was added to
20 ml of DMF and stirred; the achieved solution was then
slowly added to GO–COCl suspension. Consequently, the
reaction temperature was raised to 100ꢀC and the mix-
ture was stirred for 24 h. Finally, the reaction tempera-
ture was reduced down to 80ꢀC, and the mixture was
kept under static conditions for 24 h. The resulting solid
was filtered and washed several times with deionized
water. Next, it was dried at room temperature before
characterization.
ORCID
REFERENCES
[1] Y. Ma, Y. Chen, Natl. Sci. Rev. 2015, 2, 40.
[2] J. Liu, G. Hu, Y. Yang, H. Zhang, W. Zuo, W. Liu, B. Wang,
Nanoscale 2016, 8, 2787.
[3] C. Li, G. Shi, Nanoscale 2012, 4, 5549.
[4] L. Zhang, G. Shi, J. Phys. Chem. C 2011, 115, 17206.
[5] X. Yang, J. Zhu, L. Qiu, D. Li, Adv. Mater. 2011, 23, 2833.
[6] Z. Tang, S. Shen, J. Zhuang, X. Wang, Angew. Chem. Int. Ed.
2010, 49, 4603.
[7] C. Hu, X. Zhai, Y. Zhao, K. Bian, J. Zhang, L. Qu, H. Zhang,
H. Luo, Nanoscale 2014, 6, 2768.
[8] X. Wang, L. L. Lu, Z. L. Yu, X. W. Xu, Y. R. Zheng, S. H. Yu,
Angew. Chem. Int. Ed. 2015, 54, 2397.
4.6 | Synthesis of GOF-embedded Pd NPs
(Pd@GOF)
[9] (a) J. W. Burress, S. Gadipelli, J. Ford, J. M. Simmons,
W. Zhou, T. Yildirim, Angew. Chem. Int. Ed. 2010, 49, 8902. (b)
R. Kumar, V. M. Suresh, T. K. Maji, C. N. R. Rao, Chem.
Commun. 2014, 50, 2015.
[10] (a) H. Hu, Z. Zhao, W. Wan, Y. Gogotsi, J. Qiu, Adv. Mater.
2013, 25, 2219. (b) Y. Zhang, S. Zhang, J. Gao, T. S. Chung,
J. Membr. Sci. 2016, 515, 230.
[11] (a) G. Tang, Z. G. Jiang, X. Li, H. B. Zhang, A. Dasari,
Z. Z. Yu, Carbon 2014, 77, 592. (b) Y. Lu, L. Zhang, K. Leng,
Y. Huang, X. Yang, M. Zhang, F. Zhang, T. Zhang, Y. Chen,
Chin. Sci. Bull. 2014, 59, 1809.
The GOF (50 mg) was dispersed in 20 ml of ethanol by
sonication for 30 min. Subsequently, PdCl2 (0.25 mmol,
44.3 mg) was added, and the mixture was subjected to
sonication for 5 min. The reaction was then stirred for
24 h at room temperature. The final product was filtered
and washed with distilled water five times, and the cata-
lyst (Pd@GOF) was air-dried.
[12] W. Wan, L. Li, Z. Zhao, H. Hu, X. Hao, D. A. Winkler, L. Xi,
T. C. Hughes, J. Qiu, Adv. Funct. Mater. 2014, 24, 4915.
[13] (a) T. P. N. Tran, A. Thakur, D. X. Trinh, A. T. N. Dao,
T. Taniike, Appl. Catal. A. Gen. 2018, 549, 60. (b)
J. W. Burress, S. Gadipelli, J. Ford, J. M. Simmons, W. Zhou,
T. Yildirim, Angew. Chem. Int. Ed. 2010, 49, 8902.
[14] B. Feng, K. Xu, A. Huangm, Desalination 2016, 394, 123.
[15] H. P. Mungse, R. Singh, H. Sugimura, N. Kumar, O. P. Khatri,
Phys. Chem. Chem. Phys. 2015, 17, 20822.
4.7 | General procedure for the Heck
reaction
In a 25 ml round-bottom flask, 1 mg of Pd@GOF catalyst
(0.2 mol% Pd) was dispersed in 5 ml of H2O–EtOH (1:1)
by sonication for 20 min at room temperature. To this
suspension, aryl halides (1 mmol), styrene (1.2 mmol),
and K2CO3 (1.5 mmol) were added, and the reaction mix-
ture was stirred at 80ꢀC for the required time. After the
completion of the reaction (monitored by TLC), the reac-
tion mixture was cooled down to room temperature, fil-
tered, and then washed with dichloromethane
(3 ×10 ml). The organic phase was separated and dried
[16] Y. Cui, Q. Y. Cheng, H. Wu, Z. Wei, B. H. Han, Nanoscale
2013, 5, 8367.
[17] (a) M. Sarvestani, R. Azadi, Appl. Organomet. Chem. 2017, 31,
e3667. (b) M. Sarvestani, R. Azadi, Appl. Organomet. Chem.
2018, 32, e3906. (c) M. Sarvestani, R. Azadi, Can. J. Chem.
2019, 97, 191. (d) A. Ahmadi, T. Sedaghat, R. Azadi,