RSC Advances
Paper
Hz), 8.89 (d, 1H, J ¼ 7.8 Hz), 8.40 (d, 1H, J ¼ 7.8 Hz), 8.30 (d, 1H,
J ¼ 7.8 Hz), 8.24 (s, 1H), 8.21 (s, 1H), 7.98 (t, 2H, J ¼ 7.8 Hz), 7.56
(t, 2H, J ¼ 7.2 Hz), 7.46 (t, 1H, J ¼ 7.2 Hz), 7.22 (d, 1H, J ¼ 9.6
Hz), 7.07 (d, 1H, J ¼ 8.4 Hz), 6.76 (s, 1H), 3.90–4.15 (m, 4H),
3.66–3.63 (m, 2H), 2.05–2.01 (m, 2H), 1.94–1.89 (m, 1H), 1.84–
1.80 (m, 1H), 1.73–1.67 (m, 2H), 1.41–1.25 (m, 16H), 1.15 (t, 3H, J
¼ 7.2 Hz), 0.98–0.86 (m, 12H). 13C NMR (150 MHz, CDCl3):
d 167.79, 163.54, 163.35, 163.27, 162.68, 158.57, 151.43, 147.90,
136.59, 135.91, 132.54, 131.25, 127.21, 125.82, 125.29, 124.34,
121.67, 118.50, 118.20, 114.42, 95.31, 90.09, 44.70, 44.13, 44.04,
6 K. B. Toga, W. Gu and P. Thomas, J. Mater. Chem. A, 2014, 2,
2993–2998.
7 S. Yu, Y. Chen, J. Wu, D. Xia, S. Hong, X. Wu, J. Yu, S. Zhang,
A. Peng and H. Huang, ACS Appl. Mater. Interfaces, 2018, 10,
28812–28818.
8 H. Sun, X. Song, J. Xie, P. Sun, F. Chen, Q. Zhang, Z.-K. Chen
and W. Huang, ACS Appl. Mater. Interfaces, 2017, 9, 29924–
29931.
9 I. A. Howard, F. Laquai, P. E. Keivanidis, R. H. Friend and
N. C. Greenham, J. Phys. Chem. C, 2009, 113, 21225–21232.
38.02, 37.95, 31.34, 30.85, 30.77, 28.73, 28.68, 24.14, 24.13, 10 R. Mishra, R. Regar, R. Singhal, P. Panini and G. D. Sharma,
23.98, 23.18, 23.10, 20.76, 14.16, 14.03, 10.58. MALDI-HRMS: m/
z calcd for [C59H58N4O5–H]ꢀ 934.4122; found: 934.4117.
Compound P-2. P-2 was obtained according to the procedure
similar to that of P-1, except 5 (36.2 mg, 0.10 mmol) was used
instead of 4. The pure product was obtained by column chro-
J. Mater. Chem. A, 2017, 5, 15529–15533.
11 P. E. Hartnett, A. Timalsina, H. R. Matte, N. Zhou, X. Guo,
W. Zhao, A. Facchetti, R. P. H. Chang, M. C. Hersam,
M. R. Wasielewski and T. J. Marks, J. Am. Chem. Soc., 2014,
136, 16345–16356.
matography for three times and TLC for one time (silica gel, 12 A. D. Hendsbee, J.-P. Sun, W. K. Law, H. Yan, I. G. Hill,
CH2Cl2 as the eluent). Dark green solid. Yield: 37.5 mg, 37.9%.
D. M. Spasyuk and G. C. Welch, Chem. Mater., 2016, 28,
7098–7109.
1H NMR (400 MHz, CDCl3): d 9.67 (d, 1H, J ¼ 7.8 Hz), 8.94 (d,
1H, J ¼ 7.8 Hz), 8.55 (s, 1H), 8.44 (d, 1H, J ¼ 7.8 Hz), 8.32–8.22 13 K. P. Prajitha, S. Chithiravel, K. Krishnamoorthy and
(m, 4H), 8.00 (d, 1H, J ¼ 7.8 Hz), 7.55 (t, 1H, J ¼ 7.2 Hz), 7.43 (t,
1H, J ¼ 7.2 Hz), 7.35 (d, 1H, J ¼ 8.4 Hz), 7.00 (d, 1H, J ¼ 8.4 Hz), 14 A. Sarbu, L. Biniek, J.-M. Guenet, P. J. Mesini and
6.72 (s, 1H), 4.25 (t, 2H, J ¼ 6.6 Hz), 4.17–4.08 (m, 2H), 3.98–3.88 M. Brinkmann, J. Mater. Chem. C, 2015, 3, 1235–1242.
(m, 2H), 3.65–3.62 (m, 2H), 2.09–2.05 (m, 2H), 2.02–1.98 (m, 15 S. Naqvi, M. Kumar and R. Kumar, ACS Omega, 2019, 4,
1H), 1.96–1.92 (m, 1H), 1.73–1.64 (m, 4H), 1.44–1.25 (m, 16H), 19735–19745.
1.14–1.10 (m, 6H), 0.98–0.87 (m, 12H). 13C NMR (150 MHz, 16 J. Liu, H. Lu, Y. Liu, J. Zhang, C. Li, X. Xu and Z. Bo, ACS Appl.
CDCl3): d 163.59, 163.01, 161.18, 156.94, 152.14, 147.99, 136.29, Mater. Interfaces, 2020, 12, 10746–10754.
126.00, 124.77, 124.38, 123.41, 123.07, 121.80, 121.18, 114.62, 17 C. Ramanan, A. L. Smeigh, J. E. Anthony, T. J. Marks and
95.69, 90.19, 69.45, 44.64, 44.19, 43.84, 37.99, 31.29, 30.77, M. R. Wasielewski, J. Am. Chem. Soc., 2012, 134, 386–397.
S. K. Asha, J. Mater. Chem. C, 2014, 2, 9882–9891.
´
29.85, 28.79, 24.11, 23.17, 20.73, 19.62, 14.16, 13.93, 10.60. 18 C. Huang, M. M. Sartin, M. Cozzuol, N. Siegel, S. Barlow,
MALDI-HRMS: m/z calcd for [C63H66N4O5S–H]ꢀ 990.4748;
found: 990.4787.
J. W. Perry and S. R. Marder, J. Phys. Chem. A, 2012, 116,
4305–4317.
19 Y. Xie, X. Zhang, Y. Xiao, Y. Zhang, F. Zhou, J. Qi and J. Qu,
Chem. Commun., 2012, 48, 4338–4340.
20 Y. Chen, J. Qian, X. Liu, Q. Zhuang and Z. Han, New J. Chem.,
2013, 37, 2500–2508.
Conflicts of interest
There are no conicts to declare.
21 R. Narayan and S. K. Asha, J. Mater. Chem. C, 2013, 1, 5925–
5934.
22 M. P. Aldred, G.-F. Zhang, C. Li, G. Chen, T. Chen and
M.-Q. Zhu, J. Mater. Chem. C, 2013, 1, 6709–6718.
Acknowledgements
We thank National Natural Science Foundation (21801146) and
˘
Natural Science Foundation of Heilongjiang Province (No. 23 K. Wilma, T. Unger, S. T. Kostakoglu, M. Hollfelder,
¨
¨
C. Hunger, A. Lang, A. G. Gurek, M. Thelakkat, J. Kohler,
QC2016016) for nancial support.
¨
A. Kohler, S. Gekle and R. Hildner, Phys. Chem. Chem.
Phys., 2017, 19, 22169–22176.
24 S. L. Sonawane and S. K. Asha, ACS Appl. Mater. Interfaces,
2013, 5, 12205–12214.
References
1 X.-X. Chen, X. Wu, P. Zhang, M. Zhang, B.-N. Song,
Y.-J. Huang, Z. Li and Y.-B. Jiang, Chem. Commun., 2015, 25 Y. Liu and J. Zhao, Chem. Commun., 2012, 48, 3751–3753.
51, 13630–13633.
2 X. Lu, Z. Guo, M. Feng and W. Zhu, ACS Appl. Mater.
Interfaces, 2012, 4, 3657–3662.
26 N. Rehmat, A. Toffoletti, Z. Mahmood, X. Zhang, J. Zhao and
A. Barbon, J. Mater. Chem. C, 2020, 8, 4701–4712.
27 J. Sun, F. Zhong and J. Zhao, Dalton Trans., 2013, 42, 9595–
9605.
´
3 F. J. Cespedes-Guirao, A. B. Ropero, E. Font-Sanchis,
´
´
´
´
A. Nadal, F. Fernandez-Lazaro and A. Sastre-Santos, Chem. 28 Y. Zhao, R. Duan, J. Zhao and C. Li, Chem. Commun., 2018,
Commun., 2011, 47, 8307–8309. 54, 12329–12332.
4 X. Feng, Y. An, Z. Yao, C. Li and G. Shi, ACS Appl. Mater. 29 Z. Mahmood, K. Xu, B. Kuçukoz, X. Cui, J. Zhao, Z. Wang,
¨
¨ ¨
Interfaces, 2012, 4, 614–618.
5 B. Kulkarni, M. Malhotra and M. Jayakannan, ACS Appl.
Polym. Mater., 2019, 1, 3375–3388.
A. Karatay, H. G. Yaglioglu, M. Hayvali and A. Elmali, J.
Org. Chem., 2015, 80, 3036–3049.
35846 | RSC Adv., 2020, 10, 35840–35847
This journal is © The Royal Society of Chemistry 2020