Synthesis and Photoelectric Properties of Novel Liquid Crystalline Compound Bearing Diethynyl and Naphthyl Groups with High Birefringence

doi:10.11944/j.issn.1000-0518.2016.05.150198

Chinese Journal of Applied Chemistry ›› 2016, Vol. 33 ›› Issue (5): 533-541.DOI: 10.11944/j.issn.1000-0518.2016.05.150198

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Synthesis and Photoelectric Properties of Novel Liquid Crystalline Compound Bearing Diethynyl and Naphthyl Groups with High Birefringence

GUAN Xiaolin^a,ZHANG Yang^a,FAN Hongting^a,ZHANG Donghai^a,JIA Tianming^a,LAI Shoujun^a^b^*(),LEI Ziqiang^a

^a Key Laboratory of Eco-Environment-Related Polymer Materials,Ministry of Education,Key Laboratory of Polymer Materials Ministry of Gansu Province,College of Chemistry and Chemical Engineering,Northwest Normal University,Gansu 730070,China
^b College of Chemistry & Environmental Engeering,Chongqing Three Gorges University,Chongqing 404100,China

Received:2015-06-15 Accepted:2015-12-31 Published:2016-04-29 Online:2016-04-29
Contact: LAI Shoujun
Supported by:
Supported by the National Natural Science Foundation of China(No.51363019), Specialized Research Fund for the Doctoral Program of Higher Education(No.20136203120002), Gansu Natural Science Foundation of China(No.1308RJZA120), Natural Science Foundation Project of CQ CSTC(No.cstc2012jjA50021, No.cstc2012jjA50010), Youth Fund Promotion Plan of Northwest Normal University(No.NWNU-LKQN-12-5)

Abstract

Abstract:

An asymmetric diacetylene derivative bearing naphthyl group, 4-(4-(4-(6-(hexyloxy)-2-naphthalen)-1-(1,3-butadiynyl))-3-vinyl-phenylethynyl)-N,N-dimethylbenzenamine, was successfully synthesized by multi-step Sonogashira reactions. The structure of the compound was confirmed with ¹H and ¹³C NMR spectroscopy and elemental analysis. Its liquid crystalline property and optical birefringence were characterized by differential scanning calorimetry(DSC), polarized light microscopy(POM) and Abbe refractometer. The absorption and emission spectra of the compound were obtained with the ultraviolet-visible absorption spectrometer and fluorescence spectrometer, respectively. The compound exhibits the nematic phase in liquid crystal state and high optical birefringence of 0.47. The peak of the photoluminescence(PL) of the compound in chloroform is at 470 nm and the quantum efficiency is 97%. The double-layer devices ITO/PEDOT/liquid crystal compound/Mg:Ag(10:1)/Ag(ITO:indium tin oxide, PEDOT:poly(3,4-ethylene-dioxythiophene thiophene)) is fabricated with a low onset voltage(6.75 V). The peak of electroluminescence(EL) is at 503 nm, and the maximum brightness value is 150 cd/m²(14.75 V). The diacetylene derivative is a promising material for liquid crystal display or organic light-emitting device.

Key words: nematic liquid crystal, high optical birefringence, high fluorescence quantum efficiency, organic light-emitting device

GUAN Xiaolin, ZHANG Yang, FAN Hongting, ZHANG Donghai, JIA Tianming, LAI Shoujun, LEI Ziqiang. Synthesis and Photoelectric Properties of Novel Liquid Crystalline Compound Bearing Diethynyl and Naphthyl Groups with High Birefringence[J]. Chinese Journal of Applied Chemistry, 2016, 33(5): 533-541.

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Synthesis and Photoelectric Properties of Novel Liquid Crystalline Compound Bearing Diethynyl and Naphthyl Groups with High Birefringence

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