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Acta Physico-Chimica Sinca  2017, Vol. 33 Issue (6): 1253-1260    DOI: 10.3866/PKU.WHXB201702212
ARTICLE     
Synthesis and Properties of a Series of Dinaphthosiloles
Hong-Mei QU1,*(),Ze-Peng CHONG1,Xu CHEN2,Yi-Can MEN1,Hai-Jiao SHEN1
1 Key Laboratory of Systems Bioengineering (Ministry of Education), Tianjin University, Tianjin 300072, P. R. China
2 Tianjin Kingsrial S & T Company, Limited, Tianjin 300384, P. R. China
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Abstract  

Siloles constitute an important emerging class of photoluminescent materials. A series of compounds consisting of silole cores and fused naphthalene were synthesized and characterized:6, 6-dimethyl-1, 2, 3, 4, 8, 9, 10, 11-octapropyl-6H-dinaphtho[2, 3-b:2', 3'-d]silole, 1, 2, 3, 4, 8, 9, 10, 11-octabutyl-6, 6-dimethyl-6H-dinaphtho[2, 3-b:2', 3'-d]silole, 6, 6-diphenyl-1, 2, 3, 4, 8, 9, 10, 11-octapropyl-6H-dinaphtho[2, 3-b:2', 3'-d]silole, and 1, 2, 3, 4, 8, 9, 10, 11-octabutyl-6, 6-diphenyl-6H-dinaphtho[2, 3-b:2', 3'-d]silole. These dinaphthalene-fused siloles were synthesized from diiodonaphthalene, which was prepared by a direct coupling method. Subsequent reaction in the presence of n-butyllithium yielded 3, 3'-diiodo-2, 2'-binaphthalene. Direct substitution of two chloride ions from Ph2SiCl2 or Me2SiCl2 with 3, 3'-dilithio-2, 2'-binaphthalene then yielded the multi-substituted silole. Nuclear magnetic resonance spectroscopy and high-resolution mass spectrometry were used to characterize the structures of the siloles. Their optical and electronic properties were investigated using ultraviolet-visible absorption spectroscopy, photoluminescence spectroscopy, cyclic voltammetry, and density functional theory calculations. The dinaphthalene-fused siloles exhibited similar absorption and emission peaks. Their deep highest occupied molecular orbital level at approximately -5.5 eV indicated that they were chemically stable. Differential scanning calorimetry and thermogravimetric analysis indicated that the siloles were stable up to 309℃. A multilayer electroluminescent device was fabricated using 1, 2, 3, 4, 8, 9, 10, 11-octabutyl-6, 6-dimethyl-6H-dinaphtho[2, 3-b:2', 3'-d]silole as a light-emitting layer. The resulting device produced bright blue emission, indicating that these siloles may be suitable materials in organic light-emitting devices.



Key wordsDinaphthosilole      Coupling reaction      Lithiation reaction      Cyclic voltammetry      Thermogravimetric analysis      Organic electroluminescent device     
Received: 21 December 2016      Published: 21 February 2017
MSC2000:  O649  
Fund:  the National Natural Science Foundation of China(21102099)
Corresponding Authors: Hong-Mei QU     E-mail: ququhongmei@126.com
Cite this article:

Hong-Mei QU,Ze-Peng CHONG,Xu CHEN,Yi-Can MEN,Hai-Jiao SHEN. Synthesis and Properties of a Series of Dinaphthosiloles. Acta Physico-Chimica Sinca, 2017, 33(6): 1253-1260.

URL:

http://www.whxb.pku.edu.cn/10.3866/PKU.WHXB201702212     OR     http://www.whxb.pku.edu.cn/Y2017/V33/I6/1253

 
 
 
 
 
 
 
 
Compound λabs/nma λabs-onset/nma ΔEopt/eVb λem/nm
4a 239, 299 391 3.17 411
4b 240, 300 392 3.16 410
4c 245, 303 396 3.13 418
4d 244, 304 395 3.14 416
 
 
Compound Eonsetox/V Eopt/eV EHOMO/eV ELUMO/eV
4a 1.1959 3.17 -5.50 -2.33
4b 1.1550 3.16 -5.49 -2.33
4c 1.2633 3.13 -5.56 -2.43
4d 1.2412 3.14 -5.54 -2.40
 
 
 
1 Chen H. Y. ; Hou J. ; Hayden A. E. ; Yang H. ; Houk K. N. ; Yang Y. Adv. Mater. 2010, 22 (3), 371.
2 Chen B. ; Jiang Y. ; Chen L. ; Nie H. ; He B. ; Lu P. ; Sung H. H. Y. ; Williams I. D. ; Kwork H. S. ; Qin A. ; Zhao Z. ; Tang B. Z. Chem.-Eur. J. 2014, 20 (7), 1931.
3 Shimizu M. ; Mochida K. ; Hiyama T. J.Phys. Chem. C 2011, 115 (22), 11265.
4 Shimizu M. ; Mochida K. ; Katoh M. ; Hiyama T. J.Phys. Chem. C 2010, 114 (21), 10004.
5 Toal S. J. ; Jones K. A. ; Magde D. ; Trogler W. C. J.Am. Chem. Soc. 2005, 127 (33), 11661.
6 Lu G. ; Usta H. ; Risko C. ; Wang L. ; Facchetti A. ; Ratner M. A. ; Marks T. J. J.Am. Chem. Soc. 2008, 130 (24), 7670.
7 Hou J. ; Chen H. Y. ; Zhang S. ; Li G. ; Yang Y. J.Am. Chem. Soc. 2008, 130 (48), 16144.
8 Chu T. Y. ; Lu J. ; Beaupre S. ; Zhang Y. ; Pouliot J. R. ; Wakim S. ; Zhou J. ; Leclerc M. ; Li Z. ; Ding J. ; Tao Y. J.Am. Chem. Soc. 2011, 133 (12), 4250.
9 Chen H. Y. ; Lam W. Y. ; Luo J. D. ; Ho Y. L. ; Tang B. Z. ; Zhu D. B. ; Wong M. ; Kwok H. S. Appl. Phys. Lett. 2002, 81 (4), 574.
10 Tamao K. ; Uchida M. ; Izumizawa T. ; Furukawa K. ; Yamaguchi S. J.Am. Chem. Soc. 1996, 118 (47), 11974.
11 Liu M. S. ; Luo J. ; Jen A. K. Y. Chem. Mater. 2003, 15 (18), 3496.
12 Chen H. ; Yang T. ; Li J. W. ; Zhang X. W. ; Qian Y. ; Xie L. H. ; Huang W. Acta Phys. -Chim. Sin. 2016, 26 (9), 2346.
12 陈昊; 杨涛; 李杰伟; 张新稳; 钱妍; 解令海黄维. 物理化学学报, 2016, 26 (9), 2346.
13 Wang F. ; Luo J. ; Yang K. X. ; Chen J. W. ; Huang F. ; Cao Y. Macromolecules 2005, 38 (6), 2253.
14 Ren Y. ; Lam J. W. Y. ; Dong Y. Q. ; Tang B. Z. ; Wong K. S. J.Phys. Chem. B 2005, 109 (3), 1135.
15 Qi Q. J. ; Wu X. M. ; Hua Y. L. ; Hou Q. C. ; Dong M. S. ; Mao Z. Y. ; Yin B. ; Yin S. G. Org. Electron. 2010, 11 (3), 503.
16 Wang M. ; Zhang D. Q. ; Zhang G. X. ; Tang Y. L. ; Wang S. ; Zhu D. B. Anal. Chem. 2008, 80 (16), 6443.
17 Taydakov I. V. ; Akkuzina A. A. ; Avetisov R. I. ; Khomyako A. V. ; Saifutyarov R. R. ; Avetissov I. C. J.Lumin. 2016, 177, 31.
18 Du X. B. ; Wang Z. Y. Chem. Commun. 2011, 47, 4276.
19 Yin S. C. ; Zhang J. ; Feng H. K. ; Zhao Z. J. ; Xu L. W. ; Qiu H. Y. ; Tang B. Z. Dyes Pigm. 2012, 95 (2), 174.
20 Zhang Q. W. ; An K. ; He W. Angew. Chem. 2014, 126 (22), 5773.
21 Murai M. ; Matsumoto K. ; Takeuchi Y. ; Takai K. Org. Lett. 2015, 17 (12), 3102.
22 Ohshita J. ; Lee K. H. ; Kimura K. ; Kunai A. Organometallics 2004, 23 (23), 5622.
23 Ohshita J. ; Kai H. ; Sumida T. ; Kunai A. ; Adachi A. ; Sakamaki K. ; Okita K. J.Organomet. Chem. 2002, 642 (1-2), 137.
24 Kunai A. ; Ohshita J. ; Iida T. ; Kanehara K. ; Adachi A. ; Okita K. Synth. Met. 2003, 137 (1-3), 1007.
25 Song X. N. ; Wang G. W. ; Chang Y. ; Ma Y. ; Wang C. K. Acta Phys. -Chim. Sin. 2016, 32 (4), 943.
25 宋秀能; 王广伟; 常燕; 马勇; 王传奎. 物理化学学报, 2016, 32 (4), 943.
26 Liang Y. ; Geng W. Z. ; Wei J. N. ; Xi Z. F. Angew. Chem.-Ger. Edit. 2012, 124 (8), 1970.
27 Volz H. ; Kowarsch H. J.Organomet. Chem. 1977, 136 (2), c27.
28 Zhao J. C. ; Qiu D. F. ; Shi J. W. ; Wang H. J.Org. Chem. 2012, 77 (6), 2929.
29 Yasuike S. ; Hagiwara J. ; Danjo H. ; Kawahata M. ; Kakusawa N. ; Yamaguchi K. ; Kurita J. Heterocycles 2009, 78 (12), 3001.
30 Bayrak R. ; Ak?ay H. T. ; Durmu? M. ; De?irmencio?lu ?. J.Organomet. Chem. 2011, 696 (23), 3807.
31 Zhao Z. J. ; Liu D. D. ; Mahtab F. ; Xin L. Y. ; Shen Z. F. ; Yu Y. ; Chan C. Y. K. ; Lu P. ; Lam J. W. Y. ; Sung H. H. Y. ; Williams I. D. ; Yang B. ; Ma Y. G. ; Tang B. Z. Chem.-Eur. J. 2011, 17 (21), 5998.
32 Yamaguchi S. ; Jin R. Z. ; Tamao K. J.Organomet. Chem. 1998, 559 (1-2), 73.
33 Siddiqui S. A. ; Al-Hajry A. ; Al-Assiri M. S. Int. J.Quantum Chem. 2016, 116 (5), 339.
34 Foresman J. B. ; Head-Gordon M. ; Pople J. A. ; Frisch M. J. J.Phys. Chem. 1992, 96 (1), 135.
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