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Acta Phys. -Chim. Sin.  2017, Vol. 33 Issue (6): 1253-1260    DOI: 10.3866/PKU.WHXB201702212
Synthesis and Properties of a Series of Dinaphthosiloles
QU Hong-Mei1, CHONG Ze-Peng1, CHEN Xu2, MEN Yi-Can1, SHEN Hai-Jiao1
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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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  

The project was supported by the National Natural Science Foundation of China (21102099).

Corresponding Authors: QU Hong-Mei     E-mail:
Cite this article:

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

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