Page 15 of 16
Journal of Materials Chemistry C
DOI: 10.1039/C8TC02993H
desiccator, the desired product (4) was isolated as a red powder (0.105 g, 34%); δ (CDCl , 400.13 MHz) 8.17
H 3
(2H, J 3.9 Hz, ArH), 7.97 (2H, s, ArH), 7.90-7.84 (4H, m, ArH), 7.78 (2H, d, J 8.2 Hz, ArH), 7.76-7.72 (4H, m, ArH),
7
1
.69 (2H, s, ArH), 7.61 (2H, d, J 7.6 Hz, ArH), 7.58 (2H, d, J 8.1 Hz, ArH), 7.54 (2H, d, J 3.9, ArH), 7.31 (2H, td, J
†
5.2, 7.0, 1.2 Hz, ArH), 7.25 , 7.12 (2H, s, ArH), 2.10 (8H, m, CH
2 2
), 1.19-1.01 (24H, m, CH ), 0.75 (12H, J 6.97 Hz,
CH
3
), 0.68 (8H, m, CH
2
); δ
C
(CDCl
3
, 100.76 MHz) 156.7, 155.1, 152.8, 152.1, 151.8, 146.5, 141.3, 140.7, 138.6,
1
1
C
2
33.3, 129.6, 129.5, 128.8, 125.9, 125.5, 125.1, 124.3, 124.3, 124.2, 123.1, 120.9, 120.5, 120.3, 120.2, 119.3,
11.3, 101.4, 55.6, 40.6, 31.6, 29.8, 24.0, 22.6, 14.2; m/z (MALDI-TOF) 1196.15; HRMS calculated for
+
80
H
80
N
2
†
2
O S
3
: (M+H) , 1197.5455. Found: 1197.5450; TGA: 5% mass loss at 408°C; T
m
(DSC) = 224°C, m.p. 232-
34°C. integration not possible due to overlap with CDCl
3
peak. Use of CD
2
Cl
2
not suitable due to aggregation
causing broad signals.
References
1
2
3
.
.
.
C. W. Tang and S. A. VanSlyke, Appl. Phys. Lett., 1987, 51, 913-915.
Y. R. Cho, H. S. Kim, Y. J. Yu and M. C. Suh, Sci Rep, 2015, 5, 15903.
L. Duan, L. Hou, T.-W. Lee, J. Qiao, D. Zhang, G. Dong, L. Wang and Y. Qiu, J. Mater. Chem.,
2
010, 20, 6392-6407.
A. C. Grimsdale, K. Leok Chan, R. E. Martin, P. G. Jokisz and A. B. Holmes, Chem. Rev., 2009,
09, 897-1091.
4
.
1
5
6
7
.
.
.
M. Zhu and C. Yang, Chem. Soc. Rev., 2013, 42, 4963-4976.
A. L. Kanibolotsky, I. F. Perepichka and P. J. Skabara, Chem. Soc. Rev., 2010, 39, 2695-2728.
A. A. Zakhidov, J.-K. Lee, H. H. Fong, J. A. DeFranco, M. Chatzichristidi, P. G. Taylor, C. K. Ober
and G. G. Malliaras, Adv. Mater., 2008, 20, 3481-3484.
8
.
J.-K. Lee, M. Chatzichristidi, A. A. Zakhidov, P. G. Taylor, J. A. DeFranco, H. S. Hwang, H. H.
Fong, A. B. Holmes, G. G. Malliaras and C. K. Ober, J. Am. Chem. Soc., 2008, 130, 11564-
1
1565.
9
1
.
0.
K. S. Yook and J. Y. Lee, Adv. Mater., 2014, 26, 4218-4233.
T. M. Eggenhuisen, Y. Galagan, A. F. K. V. Biezemans, T. M. W. L. Slaats, W. P. Voorthuijzen, S.
Kommeren, S. Shanmugam, J. P. Teunissen, A. Hadipour, W. J. H. Verhees, S. C. Veenstra, M.
J. J. Coenen, J. Gilot, R. Andriessen and W. A. Groen, J. Mater. Chem. A, 2015, 3, 7255-7262.
T. M. Eggenhuisen, Y. Galagan, E. W. C. Coenen, W. P. Voorthuijzen, M. W. L. Slaats, S. A.
Kommeren, S. Shanmuganam, M. J. J. Coenen, R. Andriessen and W. A. Groen, Sol. Energy
Mater. Sol. Cells, 2015, 134, 364-372.
1
1.
1
1
1
2.
3.
4.
H. Xu, R. Chen, Q. Sun, W. Lai, Q. Su, W. Huang and X. Liu, Chem. Soc. Rev., 2014, 43, 3259-
3
302.
D. Chen, X. Cai, X.-L. Li, Z. He, C. Cai, D. Chen and S.-J. Su, J. Mater. Chem. C, 2017, 5, 5223-
231.
5
P. Data, P. Pander, M. Okazaki, Y. Takeda, S. Minakata and A. P. Monkman, Angew. Chem.
Int. Ed., 2016, 55, 5739–5744.
1
1
5.
6.
Y. Wong Michael and E. Zysman-Colman, Adv. Mater., 2017, 29, 1605444.
M. Shimizu, R. Kaki, Y. Takeda, T. Hiyama, N. Nagai, H. Yamagishi and H. Furutani, Angew.
Chem. Int. Ed. Engl., 2012, 51, 4095-4099.
1
1
1
2
2
7.
8.
9.
0.
1.
T. Khanasa, N. Prachumrak, R. Rattanawan, S. Jungsuttiwong, T. Keawin, T. Sudyoadsuk, T.
Tuntulani and V. Promarak, Chem. Commun., 2013, 49, 3401-3403.
N. Prachumrak, S. Pojanasopa, S. Namuangruk, T. Kaewin, S. Jungsuttiwong, T. Sudyoadsuk
and V. Promarak, ACS Appl. Mater. Interfaces, 2013, 5, 8694-8703.
L. Yao, S. Zhang, R. Wang, W. Li, F. Shen, B. Yang and Y. Ma, Angew. Chem. Int. Ed. Engl.,
2
014, 53, 2119-2123.
N. J. Findlay, B. Breig, C. Forbes, A. R. Inigo, A. L. Kanibolotsky and P. J. Skabara, J. Mater.
Chem. C, 2016, 4, 3774-3780.
M. Sims, D. D. C. Bradley, M. Ariu, M. Koeberg, A. Asimakis, M. Grell and D. G. Lidzey, Adv.
Funct. Mater., 2004, 14, 765-781.