Synthesis and Electroluminescent Properties of a Liquid Crystalline Linear Conjugated Arylacetylene Derivative
- Corresponding author: LAI Shoujun, shoujunlai@163.com
Citation:
GUAN Xiaolin, MENG Li, JIA Tianming, JIN Qijun, LU Baocui, LAI Shoujun. Synthesis and Electroluminescent Properties of a Liquid Crystalline Linear Conjugated Arylacetylene Derivative[J]. Chinese Journal of Applied Chemistry,
;2018, 35(4): 426-435.
doi:
10.11944/j.issn.1000-0518.2018.04.170206
Zhang C W, Qiao B, Zhao S L. Transient Analysis on Stored Charges in Organic Light-emitting Diodes and Their Application in Alternating Current Driven Electroluminescence[J]. Org Electron, 2016,39:348-353. doi: 10.1016/j.orgel.2016.10.019
Klaus K, Christoph G, Pablo M. Atomic-Scale Imaging and Spectroscopy of Electroluminescence at Molecular Interfaces[J]. Chem Rev, 2017,117(7):5174-5222. doi: 10.1021/acs.chemrev.6b00645
Hiroki T, Naoya A, Yu H. Tunable Full-Color Electroluminescence from All-Organic Optical Upconversion Devices by Near-Infrared Sensing[J]. ACS Photonics, 2017,4(2):223-227. doi: 10.1021/acsphotonics.6b00964
Michael C C, Lydia S V, Herv B. Ordinary and Hot Electroluminescence from Single-Molecule Devices:Controlling the Emission Color by Chemical Engineering[J]. Nano Lett, 2016,16(10):6480-6484. doi: 10.1021/acs.nanolett.6b02997
PENG Sai, CHEN Kai, SHENG Yafei. Research Progress on Materials for Organic Light-emitting Diodes(OLEDs)[J]. Mater Rev, 2015,29(3):41-56.
Jadhav T, Choi J M, Dhokale B. Effect of End Groups on Mechanochromism and Electroluminescence in Tetraphenylethylene Substituted Phenanthroimidazoles[J]. J Phys Chem C, 2016,120(33):18487-1849. doi: 10.1021/acs.jpcc.6b06277
Lee J, Park J. Synthesis and Electroluminescence of Novel Pyrene-Fused Chromophores[J]. Org Lett, 2015,17(16):3960-3963. doi: 10.1021/acs.orglett.5b01793
Boudreault P L T, Hennek J W, Loser S. New Semiconductors Based on 2, 2'-Ethyne-1, 2-diylbis[3-(alk-1-yn-1-yl) thiophene] for Organic Opto-Electronics[J]. Chem Mater, 2012,24(15):2929-2942. doi: 10.1021/cm301095x
Charvet R, Yamamoto Y, Sasaki T. Segregated and Alternately Stacked Donor/Acceptor Nanodomains in Tubular Morphology Tailored with Zinc Porphyrin-C60 Amphiphilic Dyads:Clear Geometrical Effects on Photoconduction[J]. J Am Chem Soc, 2012,134(5):2524-2527. doi: 10.1021/ja211334k
Silvestri F, Marrocchi A, Seri M. Solution-Processable Low-Molecular Weight Extended Arylacetylenes:Versatile p-Type Semiconductors for Field-Effect Transistors and Bulk Heterojunction Solar Cells[J]. J Am Chem Soc, 2010,132(17):6108-6123. doi: 10.1021/ja910420t
Jesus R C, Natsuhiro S, Masashi S. Synthesis of Poly(1-chloro-2-arylacetylene)s with High Cis-content and Examination of Their Absorption/Emission Properties[J]. J Polym Sci Part A:Polym Chem, 2017,55(3):382-388. doi: 10.1002/pola.v55.3
Daniel P I, Christian W. Enantioselective Sensing of Amines Based on[1+1] -, [2+2] -, and[1+2] -Condensation with Fluxional Arylacetylene-Derived Dialdehydes[J]. Org Lett, 2011,13(10):2602-2605. doi: 10.1021/ol200574x
Li Y H, Zhang G X, Zhang W. Arylacetylene-Substituted Naphthalene Diimides with Dual Functions:Optical Waveguides and n-Type Semiconductors[J]. Chem Asian J, 2014,9(11):3207-3214. doi: 10.1002/asia.201402768
Breen C A, Tischler J R, Bulovic V. Highly Efficient Blue Electroluminescence from Poly(phenylene ethynylene) via Energy Transfer from a Hole-Transport Matrix[J]. Adv Mater, 2005,17(16):1981-1985. doi: 10.1002/(ISSN)1521-4095
Flamini R, Tomasi I, Marrocchi A. Synthesis and Photobehaviour of Donor-π-Acceptor Conjugated Arylacetylenes Original Research Article[J]. J Photochem Photobiol A, 2011,223(2/3):140-148.
FANG Jingkun, YU Xian, YANG Xin. Synthesis of Diphenylamino-Substituted Arylene-Ethynylenes and Photovoltaic Properties[J]. Chinese J Org Chem, 2012,32(7):1261-1269.
Flatt A K, Yao Y X, Tour J M. Orthogonally Functionalized Oligomers for Controlled Self-Assembly[J]. J Org Chem, 2004,69(5):1752-1755. doi: 10.1021/jo035821b
Fasina T M, Collings J C, Burke J M. Synthesis, Optical Properties, Crystal Structures and Phase Behaviour of Symmetric, Conjugated Ethynylarene-based Rigid Rods with Terminal Carboxylate Groups[J]. J Mater Chem, 2005,15(6):690-697. doi: 10.1039/B413514H
ZHAO Qiangqin, LIU Meiling, LI Haitao. Synthesis of a Class of Novel Conjugated Oligo-Phenylene-Ethynylenes with Terminal Amine and Their Photoelectricity Property[J]. Chinese J Synth Chem, 2009,17(6):665-669.
Fang J, An D L, Toyaota S. Synthesis and Spectroscopic Study of Phenylene-(poly)-ethynylenes Substituted by Amino or Amino/Cyano Groups at Terminal(s):Electronic Effect of Cyano Group on Charge-transfer Excitation of Acetylenic π-Systems[J]. Tetrahedron, 2010,66(29):5479-5485. doi: 10.1016/j.tet.2010.05.016
Hirata Y, Okada T, Nomoto T. Significant Quenching of the Photoinduced Charge Separated State of Aminophenyl(phenyl)acetylene and N, N-Dimethylaminophenyl(phenyl)acetylene in Protic Solvents[J]. J Phys Chem A, 1998,102(33):6585-6589. doi: 10.1021/jp980991r
Adam D, Schuhmacher P, Simmerer J. Fast Photoconduction in the Highly Ordered Columnar Phase of a Discotie Liquid Crystal[J]. Adv Mater, 1995,7(16):43-45.
ZHU Fengzhi, YANG Gang, LI Lu. A New EL Device Based on Pt Complex Phosphorescent Materials with Liquid Crystal[J]. J Optoelectron Laser, 2010,21(6):829-832.
GUAN Xiaolin, ZHANG Yang, FAN Hongting. Synthesis and Photoelectric Properties of Novel Liquid Crystalline Compound Bearing Diethynyl and Naphthyl Groups with High Birefringence[J]. Chinese J Appl Chem, 2016,33(5):533-541. doi: 10.11944/j.issn.1000-0518.2016.05.150198
Zhang Z L, Zhang L Y, Shen Z H. Synthesis and Properties of Mesogen-Jacketed Liquid Crystalline Polymers Containing Bistolane Mesogen[J]. J Polym Sci Part A:Polym Chem, 2010,48(21):4627-4639. doi: 10.1002/pola.v48:21
Fang J, An D L, Toyaota S. Synthesis and Spectroscopic Study of Diphenylamino-substituted Phenylene-(poly)ethynylenes:Remarkable Effect of Acetylenic Conjugation Modes[J]. Tetrahedron Lett, 2010,51(6):917-920. doi: 10.1016/j.tetlet.2009.12.023
Zehua Zhang , Haitao Yu , Yanyu Qi . Design Strategy for Thermally Activated Delayed Fluorescence Materials with Multiple Resonance Effect. Acta Physico-Chimica Sinica, 2025, 41(1): 100006-0. doi: 10.3866/PKU.WHXB202309042
YanYuan Jia , Rong Rong , Jie Liu , Jing Guo , GuoYu Jiang , Shuo Guo . Unity is Strength, and Independence Shines: A Science Popularization Experiment on AIE and ACQ Effects. University Chemistry, 2024, 39(9): 349-358. doi: 10.12461/PKU.DXHX202402035
Fan JIA , Wenbao XU , Fangbin LIU , Haihua ZHANG , Hongbing FU . Synthesis and electroluminescence properties of Mn2+ doped quasi-two-dimensional perovskites (PEA)2PbyMn1-yBr4. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1114-1122. doi: 10.11862/CJIC.20230473
Qin Li , Kexin Yang , Qinglin Yang , Xiangjin Zhu , Xiaole Han , Tao Huang . Illuminating Chlorophyll: Innovative Chemistry Popularization Experiment. University Chemistry, 2024, 39(9): 359-368. doi: 10.3866/PKU.DXHX202309059
Xiao SANG , Qi LIU , Jianping LANG . Synthesis, structure, and fluorescence properties of Zn(Ⅱ) coordination polymers containing tetra-alkenylpyridine ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2124-2132. doi: 10.11862/CJIC.20240158
Feng Lu , Tao Wang , Qi Wang . Preparation and Characterization of Water-Soluble Silver Nanoclusters: A New Design and Teaching Practice in Materials Chemistry Experiment. University Chemistry, 2025, 40(4): 375-381. doi: 10.12461/PKU.DXHX202406005
Chen LU , Qinlong HONG , Haixia ZHANG , Jian ZHANG . Syntheses, structures, and properties of copper-iodine cluster-based boron imidazolate framework materials. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 149-154. doi: 10.11862/CJIC.20240407
Zishuo Yi , Peng Liu , Yan Xu . Fluorescent “Chameleon”: A Popular Science Experiment Based on Dynamic Luminescence. University Chemistry, 2024, 39(9): 304-310. doi: 10.12461/PKU.DXHX202311079
Shuwen SUN , Gaofeng WANG . Two cadmium coordination polymers constructed by varying Ⅴ-shaped co-ligands: Syntheses, structures, and fluorescence properties. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 613-620. doi: 10.11862/CJIC.20230368
Dongdong YANG , Jianhua XUE , Yuanyu YANG , Meixia WU , Yujia BAI , Zongxuan WANG , Qi MA . Design and synthesis of two coordination polymers for the rapid detection of ciprofloxacin based on triphenylpolycarboxylic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2466-2474. doi: 10.11862/CJIC.20240266
Jiming XI , Yukang TENG , Rui ZHANG , Zhenzhong LU . Fluorescent coordination polymers based on anthracene-and pyrene-derivative ligands. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 847-854. doi: 10.11862/CJIC.20240367
Yuanyu YANG , Jianhua XUE , Yujia BAI , Lulu CUI , Dongdong YANG , Qi MA . Design, synthesis, and detection of Al3+ of two zinc complexes based on Schiff base ligands. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1207-1216. doi: 10.11862/CJIC.20250005
Yanfen PENG , Xinyue WANG , Tianbao LIU , Xiaoshuo WU , Yujing WEI . Syntheses and luminescence of four Cd(Ⅱ)/Zn(Ⅱ) complexes constructed by 1,3‐bis(4H‐1,2,4‐triazole)benzene. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1416-1426. doi: 10.11862/CJIC.20250018
Youbo HU , Donggang LI , Changhua SUN , Zhenzhong LU , Songjun GU . Coordination polymers based on anthracene- and pyrene-derived ligands: Crystal structure, fluorescent property, and framework isomerization. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1681-1688. doi: 10.11862/CJIC.20250004
Lin Song , Dourong Wang , Biao Zhang . Innovative Experimental Design and Research on Preparing Flexible Perovskite Fluorescent Gels Using 3D Printing. University Chemistry, 2024, 39(7): 337-344. doi: 10.3866/PKU.DXHX202310107
Han ZHANG , Jianfeng SUN , Jinsheng LIANG . Hydrothermal synthesis and luminescent properties of broadband near-infrared Na3CrF6 phosphor. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 349-356. doi: 10.11862/CJIC.20240098
Yanglin Jiang , Mingqing Chen , Min Liang , Yige Yao , Yan Zhang , Peng Wang , Jianping Zhang . Experimental and Theoretical Investigations of Solvent Polarity Effect on ESIPT Mechanism in 4′-N,N-diethylamino-3-hydroxybenzoflavone. Acta Physico-Chimica Sinica, 2025, 41(2): 100012-0. doi: 10.3866/PKU.WHXB202309027
Yingpeng ZHANG , Xingxing LI , Yunshang YANG , Zhidong TENG . A pyrazole-based turn-off fluorescent probe for visual detection of hydrazine. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1301-1308. doi: 10.11862/CJIC.20250064
Xuewei BA , Cheng CHENG , Huaikang ZHANG , Deqing ZHANG , Shuhua LI . Preparation and luminescent performance of Sr1-xZrSi2O7∶xDy3+ phosphor with high thermal stability. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 357-364. doi: 10.11862/CJIC.20240096
Yan ZHAO , Jiaxu WANG , Zhonghu LI , Changli LIU , Xingsheng ZHAO , Hengwei ZHOU , Xiaokang JIANG . Gd3+-doped Sc2W3O12: Eu3+ red phosphor: Preparation and luminescence performance. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 461-468. doi: 10.11862/CJIC.20240316