Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (11): 4400-4408.DOI: 10.6023/cjoc202105023 Previous Articles Next Articles
ARTICLES
周敏a,b, 李晶b, 程杰b, 葛从伍b,*(), 程探宇a,*(
), 高希珂b,*(
)
收稿日期:
2021-05-12
修回日期:
2021-07-15
发布日期:
2021-08-17
通讯作者:
葛从伍, 程探宇, 高希珂
基金资助:
Min Zhoua,b, Jing Lib, Jie Chengb, Congwu Geb(), Tanyu Chenga(
), Xike Gaob(
)
Received:
2021-05-12
Revised:
2021-07-15
Published:
2021-08-17
Contact:
Congwu Ge, Tanyu Cheng, Xike Gao
Supported by:
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Min Zhou, Jing Li, Jie Cheng, Congwu Ge, Tanyu Cheng, Xike Gao. Synthesis and Field-Effect Characteristics of the Chiral Naphthalene Diimide Derivatives[J]. Chinese Journal of Organic Chemistry, 2021, 41(11): 4400-4408.
Compd. | λmax/nm | Ega/eV | Tdb/℃ | Tptc/℃ | |
---|---|---|---|---|---|
Solid | Film | Heating/Cooling | |||
I-R | 630 | 639 | 1.78 | 416 | 277/283 |
I-S | 630 | 639 | 1.78 | 416 | 277/283 |
I-R,S | 630 | 644 | 1.78 | 418 | 277/287 |
I-rac | 630 | 644 | 1.78 | 424 | 285/292 |
Compd. | λmax/nm | Ega/eV | Tdb/℃ | Tptc/℃ | |
---|---|---|---|---|---|
Solid | Film | Heating/Cooling | |||
I-R | 630 | 639 | 1.78 | 416 | 277/283 |
I-S | 630 | 639 | 1.78 | 416 | 277/283 |
I-R,S | 630 | 644 | 1.78 | 418 | 277/287 |
I-rac | 630 | 644 | 1.78 | 424 | 285/292 |
Compd. | Annealing temperature/℃ | µh,max/ (cm2•V–1•s–1) | VT/V | IOn/IOff |
---|---|---|---|---|
I-R | As-spun | 3.2×10–5 | 6.1 | 102~103 |
100 | 4.0×10–2 | –62.9 | 104~105 | |
180 | 4.6×10–3 | –40.4 | 103~104 | |
I-S | As-spun | 3.8×10–5 | 1.8 | 102~103 |
100 | 3.6×10–2 | –62.4 | 104~105 | |
180 | 4.6×10–3 | –42.6 | 103~104 | |
I-R,S | As-spun | 4.9×10–5 | 2.9 | 102~103 |
100 | 7.4×10–2 | –50.6 | 104~105 | |
180 | 1.4×10–2 | –40.0 | 104~105 | |
I-rac | As-spun | 1.7×10–5 | 3.0 | 102~103 |
100 | 7.5×10–2 | –62.5 | 104~105 | |
180 | 1.5×10–2 | –37.0 | 104~105 |
Compd. | Annealing temperature/℃ | µh,max/ (cm2•V–1•s–1) | VT/V | IOn/IOff |
---|---|---|---|---|
I-R | As-spun | 3.2×10–5 | 6.1 | 102~103 |
100 | 4.0×10–2 | –62.9 | 104~105 | |
180 | 4.6×10–3 | –40.4 | 103~104 | |
I-S | As-spun | 3.8×10–5 | 1.8 | 102~103 |
100 | 3.6×10–2 | –62.4 | 104~105 | |
180 | 4.6×10–3 | –42.6 | 103~104 | |
I-R,S | As-spun | 4.9×10–5 | 2.9 | 102~103 |
100 | 7.4×10–2 | –50.6 | 104~105 | |
180 | 1.4×10–2 | –40.0 | 104~105 | |
I-rac | As-spun | 1.7×10–5 | 3.0 | 102~103 |
100 | 7.5×10–2 | –62.5 | 104~105 | |
180 | 1.5×10–2 | –37.0 | 104~105 |
[1] |
Kuang, H.; Xu, C.; Tang, Z. Adv. Mater. 2020, 32, 2005110.
doi: 10.1002/adma.v32.41 |
[2] |
Liu, M. Acta Phys. Chim. Sin. 2020, 36, 2004031. (in Chinese)
|
(刘鸣华, 物理化学学报, 2020, 36, 2004031.)
|
|
[3] |
Liu, J.; Yin, F.; Hu, J.; Ju, Y. Chin. J. Org. Chem. 2021, 41, 1031. (in Chinese)
doi: 10.6023/cjoc202008011 |
(刘金果, 殷凤, 胡君, 巨勇, 有机化学, 2021, 41, 1031.)
doi: 10.6023/cjoc202008011 |
|
[4] |
Pasteur, L. Ann. Chim. Phys. 1848, 24, 442.
|
[5] |
Reinitzer, F. Monatsh. Chem. 1888, 9, 421.
doi: 10.1007/BF01516710 |
[6] |
Geng, Y.; Trajkovska, A.; Culligan, S. W.; Ou, J. J.; Chen, H. M. P.; Katsis, D.; Chen, S. H. J. Am. Chem. Soc. 2003, 125, 14032.
doi: 10.1021/ja037733e |
[7] |
Yang, Y.; da Costa, R. C.; Smilgies, D. M.; Campbell, A. J.; Fuchter, M. J. Adv. Mater. 2013, 25, 2624.
doi: 10.1002/adma.v25.18 |
[8] |
Liu, J.; Su, H.; Meng, L.; Zhao, Y.; Deng, C.; Ng, J. C. Y.; Lu, P.; Faisal, M.; Lam, J. W. Y.; Huang, X.; Wu, H.; Wong, K. S.; Tang, B. Chem. Sci. 2012, 3, 2737.
doi: 10.1039/c2sc20382k |
[9] |
Hatakeyama, T.; Hashimoto, S.; Oba, T.; Nakamura, M. J. Am. Chem. Soc. 2012, 134, 19600.
doi: 10.1021/ja310372f pmid: 23167918 |
[10] |
Liu, J.; Zhang, Y.; Phan, H.; Sharenko, A.; Moonsin, P.; Walker, B.; Promarak, V.; Nguyen, T. Q. Adv. Mater. 2013, 25, 3645.
doi: 10.1002/adma.v25.27 |
[11] |
Ying, Y.; Rice, B.; Shi, X.; Brandt, J. R.; Correa da Costa, R.; Hedley, G. J.; Smilgies, D. M.; Frost, J. M.; Samuel, I. D. W.; Otero-de-la-Roza, A.; Johnson, E. R.; Jelfs, K. E.; Nelson, J.; Campbell, A. J.; Fuchter, M. J. ACS Nano 2017, 11, 8329.
doi: 10.1021/acsnano.7b03540 pmid: 28696680 |
[12] |
Chen, M.; Jiao, X. C.; Li, J.; Wu, W.; Xin, H.; McNeill, C. R.; Gao, X. Langmuir 2019, 35, 6188.
doi: 10.1021/acs.langmuir.9b00463 |
[13] |
Sakai, N.; Mareda, J.; Vauthey, E.; Matile. Chem. Commun. 2010, 46, 4225.
doi: 10.1039/c0cc00078g |
[14] |
Bhosale, S. V.; Bhosale, S. V.; Bhargava, S. K. Org. Biomol. Chem. 2012, 10, 6455.
doi: 10.1039/c2ob25798j |
[15] |
Suraru, S. L.; Würthner, F. Angew. Chem., nt. Ed. 2014, 53, 7428.
|
[16] |
Guo, D.; Li, L.; Zhu, X.; Heeney, M.; Li, J.; Dong, L.; Yu, Q.; Gan, Z.; Gu, X.; Tan, L. Sci. China Chem. 2020, 63, 1198.
doi: 10.1007/s11426-020-9776-8 |
[17] |
Zhang, F.; Hu, Y.; Schuettfort, T.; Di, C.; Gao, X.; McNeill, C. R.; Thomsen, L.; Mannsfeld, S. C. B.; Yuan, W.; Sirringhaus, H.; Zhu, D. J. Am. Chem. Soc. 2013, 135, 2338.
doi: 10.1021/ja311469y |
[18] |
Zhao, Z.; Zhang, F. J.; Hu, Y.; Wang, Z.; Leng, B.; Gao, X.; Di, C.; Zhu, D. ACS Macro Lett. 2014, 3, 1174.
doi: 10.1021/mz500603f |
[19] |
Wu, W.; Zhao, Z.; Li, J.; Chen, M.; Gao, X. Asian J. Org. Chem. 2018, 7, 2279.
doi: 10.1002/ajoc.201800443 |
[20] |
Han, W.; Wang, Z.; Hu, Y.; Yang, X.; Ge, C.; Gao, X. Sci. China Chem. 2020, 63, 1182.
doi: 10.1007/s11426-020-9792-3 |
[21] |
Sasikumar, M.; Suseela, Y. V.; Govindaraju, T. Asian J. Org. Chem. 2013, 2, 779.
doi: 10.1002/ajoc.v2.9 |
[22] |
Hu, Y.; Wang, Z.; Yang, X.; Zhao, Z.; Han, W.; Yuan, W.; Li, H.; Gao, X.; Zhu, D. Tetrahedron Lett. 2013, 54, 2271.
doi: 10.1016/j.tetlet.2013.02.075 |
[23] |
Jelley, E. E. Nature 1936, 138, 1009.
doi: 10.1038/1381009a0 |
[24] |
Gao, X.; Qiu, W.; Yang, X.; Liu, Y.; Wang, Y.; Zhang, H.; Qi, T.; Liu, Y.; Lu, K.; Du, C.; Shuai, Z.; Yu, G.; Zhu, D. Org. Lett. 2007, 9, 3917
doi: 10.1021/ol701539z |
[25] |
Röger, C.; Würthner, F. J. Org. Chem. 2007, 72, 8070.
doi: 10.1021/jo7015357 |
[26] |
Gao, X.; Qiu, W.; Yang, X.; Liu, Y.; Wang, Y.; Zhang, H.; Qi, H.; Liu, Y.; Lu, K.; Du, C.; Shuai, Z.; Yu, G.; Zhu, D. Org. Lett. 2007, 9, 3917
doi: 10.1021/ol701539z |
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