Chinese Journal of Organic Chemistry >
Synthesis of Saddle-Shaped Cyclooctatetrathiophene-Triazine Derivatives and Their Aggregation Induced Emissions (AIE) Properties
Received date: 2017-10-16
Revised date: 2018-02-08
Online published: 2018-02-11
Supported by
Project supported by the National Natural Science Foundation of China (Nos. 21672053, 21672054, 21703055), and the Innovation Scientists and Technicians Troop Construction Projects of Henan Province (No. C20150011).
With saddle-shaped cyclooctatetrathiophene (COTh) and 1, 3, 5-triazine as building blocks, three derivatives bearing one, two and three COTh units are synthesized via Kumada-typed reaction. Theoretical calculations indicate that the two absorption peaks in long wavelength region are derived from intramolecular charge transfer (CT) absorption. 2, 4- Di(methoxyl)-6-(5, 8, 11-tris(trimethylsilyl)cycloocta [1, 2-b:4, 3-b':5, 6-b":8, 7-b'"]tetrathiophen-2-yl)-1, 3, 5-triazine (1), 2-meth- oxyl-4, 6-di(5, 8, 11-tris(trimethyl-silyl)cycloocta [1, 2-b:4, 3-b':5, 6-b":8, 7-b'"]tetrathiophen-2-yl)-1, 3, 5-triazine (2) and 2, 4, 6-tris- (5, 8, 11-tris(trimethylsilyl)cycloocta [1, 2-b:4, 3-b':5, 6-b":8, 7-b'"]tetrathiophen-2-yl)-1, 3, 5-triazine (3) exhibit intramolecular charge transfer (ICT) state emission peaked in region of 560～570 nm in solution at room temperature, and give both local emission of COTh peaked at 400 nm and ICT state emission peaked in region of 480～500 nm in rigid solution at 77 K. In tetrahydrofuran (THF)-H2O binary solvent system, compounds 1, 2 and 3 show typical aggregation induced emissions (AIE), which may be controlled by mechanism of restriction of intramolecular rotations (RIR) and restriction of intramolecular vibration (RIV). Crystal structure of 1 shows that intramolecular two rings of triazine and its linked thiophene are planar. There are strong C-C interactions between intermolecular rings of triazine and thiophene, which restrict the intramolecular rotation between triazine and thiophene rings. Such intermolecular C-C interactions are helpful to decrease the process of non-irradiative decay and increase AIE emission.
Zhang Weijie , Xu Li , Song Jinsheng , Ma Zhiying , Wang Hua . Synthesis of Saddle-Shaped Cyclooctatetrathiophene-Triazine Derivatives and Their Aggregation Induced Emissions (AIE) Properties[J]. Chinese Journal of Organic Chemistry, 2018 , 38(5) : 1119 -1125 . DOI: 10.6023/cjoc201710017
[1] (a) Greving, B.; Woltermann, A.; Kauffmann, T. Angew. Chem., Int. Ed. 1974, 13, 467.
(b) Kauffmann, T.; Greving, B.; König, J.; Mitschker, A.; Woltermann, A. Angew. Chem., Int. Ed. 1975, 14, 713.
[2] Kauffmann, T.; Mackowiak, H. P. Chem. Ber. 1985, 118, 2343.
[3] Marsella, M. J.; Reid, R. J. Macromolecules 1999, 32, 5982.
[4] Marsella, M. J.; Reid, R. J.; Estassi, S.; Wang, L. S. J. Am. Chem. Soc. 2002, 124, 12507.
[5] Zhang, S.; Liu, X.; Li, C.; Li, L.; Song, J.; Shi, J.; Morton, M.; Rajca, S.; Rajca, A.; Wang, H. J. Am. Chem. Soc. 2016, 138, 10002.
[6] (a) Li, L.; Zhao, C.; Wang, H. Chem. Rec. 2016, 16, 797.
(b) Zhao, C.; Xu, L.; Wang, Y.; Li, C.; Wang, H. Chin. J. Chem. 2015, 33, 71.
(c) Wang, Y.; Song, J.; Xu, L.; Kan, Y.; Shi, J.; Wang, H. J. Org. Chem. 2014, 79, 2255.
[7] (a) Duan, Y.; Xu, X.; Yan, H.; Wu, W.; Li, Z.; Peng, Q. Adv. Mater. 2017, 1605115.
(b) Lim, K.; Kang, M.-S.; Myung, Y.; Seo, J.-H.; Banerjee, P.; Marks, T. J.; Ko, J. J. Mater. Chem. A 2016, 4, 1186.
[8] (a) Anke, S.; Tatyana, S.; Edwin, K. Coord. Chem. Rev. 2013, 257, 2032.
(b) Kheria, S.; Rayavarapu, S.; Kotmale, A. S.; Gonnade, R. G.; Sanjayan, G. J. Chem.-Eur. J. 2017, 23, 783.
[9] Wang, H.; Zeng, Z.; Zeng, H.-P. Chin. J. Org. Chem. 2013, 33, 915(in Chinese). (王辉, 曾卓, 曾和平, 有机化学, 2013, 33, 915.)
[10] Xu, L.; Wang, P.-F.; Zhang, J.-J.; Wu, W.; Shi, J.-W.; Yuan, J.-F.; Han, H.; Wang, H. RSC Adv. 2015, 5, 51745.
[11] (a) Luo, J.; Xie, Z.; Lam, J. W. Y.; Cheng, L.; Tang, B. Z.; Chen, H.; Qiu, C.; Kwok, H. S.; Zhan, X.; Liu, Y. Chem. Commun. 2001, 1740.
(b) Mei, J.; Leung, N. L. C.; Kwok, R. T. K.; Lam, J. W. Y.; Tang, B. Z. Chem. Rev. 2015, 115, 11718.
[12] Wang, Y.; Gao, D. W.; Shi, J. W.; Kan, Y. H.; Song, J. S.; Li, C. L.; Wang, H. Tetrahedron 2014, 70, 631.
[13] Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A.; Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, O.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, Revision D01, Gaussian, Inc., Wallingford CT, 2013.
[14] Grimme, S.; Antony, J.; Ehrlich, S.; Krieg, H. J. Chem. Phys. 2010, 132, 154104.
[15] Goerigk, L.; Grimme, S. J. Chem. Phys. 2010, 132, 184103.
[16] Lu, T.; Chen, F. J. Comput. Chem. 2012, 33, 580.
[17] Bu, F.; Duan, R.; Xie, Y.; Yi, Y.; Peng, Q.; Hu, R.; Qin, A.; Zhao, Z.; Tang, B. Z. Angew. Chem., Int. Ed. 2015, 54, 14492.
[18] (a) Luo, J.; Song, K.; Gu, F. L.; Miao, Q. Chem. Sci. 2011, 2, 2029.
(b) Leung, N. L.; Xie, N.; Yuan, W.; Liu Y.; Wu, Q.; Peng, Q.; Miao, Q.; Lam, J. W. Y.; Tang, B. Z. Chem.-Eur. J. 2014, 20, 15349.
[19] (a) Nishiuchi, T.; Tanaka, K.; Kuwatani, Y.; Sung, J.; Nishinaga, T.; Kim, D.; Iyoda, M. Chem.-Eur. J. 2013, 19, 4110.
(b) Yuan, C.; Saito, S.; Camacho, C.; Kowalczyk, T.; Irle, S.; Yamaguchi, S. Chem.-Eur. J. 2014, 20, 2193.
[20] Yuan, C. X.; Tao, X. T.; Ren, Y.; Li, Y.; Yang, J. X.; Yu, W. T.; Wang, L.; Jiang, M. H. J. Phys. Chem. C 2007, 111, 12811.
/
| 〈 |
|
〉 |
