Citation:
QI Zheng-Jian, WEI Bin, WANG Xue-Mei, KANG Feng, HONG Man-Xin, TANG Lan-Lan, SUN Yue-Ming. Synthesis, Optical and Electrochemical Properties of Novel 3,4-Dialkyloxythiophene-Based D-A-D Organic Conjugated Molecules[J]. Acta Physico-Chimica Sinica,
;2010, 26(12): 3310-3316.
doi:
10.3866/PKU.WHXB20101201
-
Novel 3,4-dialkyloxythiophene-based D-A-D organic conjugated molecules di(2-vinyl-3,4- dialkyloxythiophene)-p-2,5-bisphenyl-1,3,4-oxadiazole [(3,4DAOTV)2-OXD] were obtained using the Wittig reaction. The structure was effectively characterized using hydrogen nuclear magnetic resonance (1H NMR), Fourier transform infrared (FTIR) spectroscopy, high pressure liquid chromatography (HPLC) and elemental analysis (EA). The optical and electrochemical properties were studied by UV-Vis, fluorescence spectroscopy, and cyclic voltammetry. The UV-Vis maximum absorption of the three studied compounds ranged between 382-383 nm and their optical bandgaps ranged from 2.92 to 2.97 eV. Their emission maxima ranged from 448 to 452 nm with a bright cyan light and their luminescence quantum yields ranged from 36.8%-37.6% in CHCl3. As solid films, these compounds emit glaucous light at 513-516 nm. The (3, 4DAOTV)2-OXDs show oxidation and reduction processes in their cyclic voltammograms. Their ionization potentials of 5.65-5.70 eV coincide with the hole transport ability of thiophenes and their electron affinity values of 2.74-2.88 eV are close to the required properties of an electron transport material. These properties will facilitate electron injection and transfer from the cathode. Theoretical calculations indicate that the D-A-D organic conjugation molecule has high coplanarity and that electrons are delocalized along its backbone, which might result in interfacial molecular self-assembly and efficient charge carrier transport as well as efficient quantum yields of devices.
-
-
-
[1]
1. McCullough, R. D.; Jayaraman, M. J. Chem. Soc. Chem. Commun., 1995: 135
-
[2]
2. Inganas, O. Trends Polym. Sci., 1994, 2: 189
-
[3]
3. Van Dort, P. C.; Pickett, J. E.; Blohm, M. L. Synth. Met., 1991, 42: 2305
-
[4]
4. Fayd, K.; Cloutier, R.; Leclerc, M. Macromolecules, 1993, 26: 2501
-
[5]
5. Chen, S. A.; Tsai, C. C. Macromolecules, 1993, 26: 2234
-
[6]
6. Ding, J. F.; Day, M.; Robertson, G. Macromolecules, 2002, 35: 3474
-
[7]
7. Loewe, R. S.; Khersonsky, S. M.; McCullough, R. D. Adv. Mater, 1999, 11: 250
-
[8]
8. Iovu, M. C.; Sheina, E. E.; Gil, R. R.; McCullough, R. D. Macromolecules, 2005, 38: 8649
-
[9]
9. Yin, S. G. Adv. Func. Mater., 2009, 19: 894
-
[10]
10. Yu,W. L.; Meng, H.; Pei, J. Macromolecules, 1998, 31: 4838
-
[11]
11. Adachi, C.; Baldo, M. A.; Forrest, S. R. Appl. Phys. Let, 2000, 77: 904
-
[12]
12. Mikroyannidis, J. A.; Spiliopoulos, L. K.; Kasimis, T. S. Macromolecules, 2003, 36: 9295
-
[13]
13. Kim, J. H.; Park, J. H.; Lee, H. Chem. Mater., 2003, 15: 3414
-
[14]
14. Wan, J. H.; Feng, J. C.;Wen, G. A.;Wei,W.; Huang,W. J. Org. Chem., 2006, 71: 2565
-
[15]
15. Guo, K. P.; Hao, J. M.; Zhang, T.; Zu, F. H. Dyes and Pigments, 2008, 77: 657
-
[16]
16. Qi, Z. J.; He, Y. F.; Sun, Y. M. Chinese Journal of Organic Chemistry, 2009, 29: 1756
-
[17]
[祁争健, 何艳芳, 孙岳明. 有机化 学, 2009, 29: 1756]
-
[18]
17. Li, D. J.; Sun, B. H.; Li, B. University Chemistry, 2003, 18: 59
-
[19]
[李德江, 孙碧海, 李斌. 大学化学, 2003, 18 : 59]
-
[20]
18. Koeckelberghs, G.; Vangheluwe, M.; Samyn, C. Macromolecules, 2005, 38: 5554
-
[21]
19. Akoudad, S.; Frere, P.; Mercier, N.; Roncali, J. J. Org. Chem., 1999, 64: 4267
-
[22]
20. Song, J. F.; Cheng, Y. X.; Chen, L.W. European Polymer Journal, 2006, 42: 663
-
[23]
21. Zhu, Y.; Kulkarni, A. P.;Wu, P. T.; Jenekhe, S. A. Molecules Chem. Mater., 2008, 20: 4200
-
[24]
22. Shen, S. J. Spectral analysis principle. Shanghai: Chemical Technology College of East China Press, 1994: 19
-
[25]
[沈淑娟. 波谱分析法. 上海: 华东化工学院出版社, 1994: 19]
-
[26]
23. Hao, Y. Y.; Hao, H. T.;Wang, H. Spectrosc. Spectr. Anal., 2004, 24: 1524
-
[27]
[郝玉英, 郝海涛, 王华. 光谱学与光谱分析, 2004, 24: 1524)
-
[28]
24. Fang, R. C. Solid spectrascopy, Hefei: Press of University of Science and Technology of China, 2008: 61
-
[29]
[方容川. 固体光谱 学.合肥: 中国科技大学出版社, 2008: 61]
-
[30]
25. Huang, C. H.; Li, F. Y.; Huang,W. Introduction to organic light emitting materials and devices. Shanghai: Fudan University Press., 2005: 27
-
[31]
[黄春辉, 李富友, 黄维. 有机电致发光材料与器件 导论. 上海: 复旦大学出版社, 2005: 27]
-
[32]
26. Crosby, G. A.; Demas, J. N. J. Phys. Chem. A., 1971, 75: 991
-
[33]
27. Garcia, P.; Penuut, J. M.; Hapiot, P.;Wiatgens, V.; Valat, P.;Gander, F.; Dehbouglise, D. J. Phys. Chem. 1993, 97: 513Optical Materials, 2007, 29: 1710
-
[34]
29. Hegde, P. K.; Adhikari, A. V.; Manjunatha, M. G.; Poornesh, P.; Umesh, G. Optical Materials, 2009, 31: 1000
-
[35]
30. Tong, L. G.; Jian, X. G.;Wang, J. Y. J. Funct. Mater., 2002, 33: 568. [佟拉嘎, 蹇锡高, 王锦艳. 功能材料, 2002, 33: 568]
-
[1]
-
-
-
[1]
Yonghui ZHOU , Rujun HUANG , Dongchao YAO , Aiwei ZHANG , Yuhang SUN , Zhujun CHEN , Baisong ZHU , Youxuan ZHENG . Synthesis and photoelectric properties of fluorescence materials with electron donor-acceptor structures based on quinoxaline and pyridinopyrazine, carbazole, and diphenylamine derivatives. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 701-712. doi: 10.11862/CJIC.20230373
-
[2]
Chongjing Liu , Yujian Xia , Pengjun Zhang , Shiqiang Wei , Dengfeng Cao , Beibei Sheng , Yongheng Chu , Shuangming Chen , Li Song , Xiaosong Liu . Understanding Solid-Gas and Solid-Liquid Interfaces through Near Ambient Pressure X-Ray Photoelectron Spectroscopy. Acta Physico-Chimica Sinica, 2025, 41(2): 100013-. doi: 10.3866/PKU.WHXB202309036
-
[3]
Tengjiao Wang , Tian Cheng , Rongjun Liu , Zeyi Wang , Yuxuan Qiao , An Wang , Peng Li . Conductive Hydrogel-based Flexible Electronic System: Innovative Experimental Design in Flexible Electronics. University Chemistry, 2024, 39(4): 286-295. doi: 10.3866/PKU.DXHX202309094
-
[4]
Zhao Lu , Hu Lv , Qinzhuang Liu , Zhongliao Wang . Modulating NH2 Lewis Basicity in CTF-NH2 through Donor-Acceptor Groups for Optimizing Photocatalytic Water Splitting. Acta Physico-Chimica Sinica, 2024, 40(12): 2405005-. doi: 10.3866/PKU.WHXB202405005
-
[5]
Yuping Wei , Yiting Wang , Jialiang Jiang , Jinxuan Deng , Hong Zhang , Xiaofei Ma , Junjie Li . Interdisciplinary Teaching Practice——Flexible Wearable Electronic Skin for Low-Temperature Environments. University Chemistry, 2024, 39(10): 261-270. doi: 10.12461/PKU.DXHX202404007
-
[6]
Jiali CHEN , Guoxiang ZHAO , Yayu YAN , Wanting XIA , Qiaohong LI , Jian ZHANG . Machine learning exploring the adsorption of electronic gases on zeolite molecular sieves. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 155-164. doi: 10.11862/CJIC.20240408
-
[7]
Yanan Jiang , Yuchen Ma . Brief Discussion on the Electronic Exchange Interaction in Quantum Chemistry Computations. University Chemistry, 2025, 40(3): 10-15. doi: 10.12461/PKU.DXHX202402058
-
[8]
Yaqin Zheng , Lian Zhuo , Meng Li , Chunying Rong . Enhancing Understanding of the Electronic Effect of Substituents on Benzene Rings Using Quantum Chemistry Calculations. University Chemistry, 2025, 40(3): 193-198. doi: 10.12461/PKU.DXHX202406119
-
[9]
Jingwen Wang , Minghao Wu , Xing Zuo , Yaofeng Yuan , Yahao Wang , Xiaoshun Zhou , Jianfeng Yan . Advances in the Application of Electrochemical Regulation in Investigating the Electron Transport Properties of Single-Molecule Junctions. University Chemistry, 2025, 40(3): 291-301. doi: 10.12461/PKU.DXHX202406023
-
[10]
Meiqing Yang , Lu Wang , Haozi Lu , Yaocheng Yang , Song Liu . Recent Advances of Functional Nanomaterials for Screen-Printed Photoelectrochemical Biosensors. Acta Physico-Chimica Sinica, 2025, 41(2): 100018-. doi: 10.3866/PKU.WHXB202310046
-
[11]
Jingzhao Cheng , Shiyu Gao , Bei Cheng , Kai Yang , Wang Wang , Shaowen Cao . 4-氨基-1H-咪唑-5-甲腈修饰供体-受体型氮化碳光催化剂的构建及其高效光催化产氢研究. Acta Physico-Chimica Sinica, 2024, 40(11): 2406026-. doi: 10.3866/PKU.WHXB202406026
-
[12]
Jinfu Ma , Hui Lu , Jiandong Wu , Zhongli Zou . Teaching Design of Electrochemical Principles Course Based on “Cognitive Laws”: Kinetics of Electron Transfer Steps. University Chemistry, 2024, 39(3): 174-177. doi: 10.3866/PKU.DXHX202309052
-
[13]
Donghui PAN , Yuping XU , Xinyu WANG , Lizhen WANG , Junjie YAN , Dongjian SHI , Min YANG , Mingqing CHEN . Preparation and in vivo tracing of 68Ga-labeled PM2.5 mimetic particles for positron emission tomography imaging. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 669-676. doi: 10.11862/CJIC.20230468
-
[14]
Jizhou Liu , Chenbin Ai , Chenrui Hu , Bei Cheng , Jianjun Zhang . 六氯锡酸铵促进钙钛矿太阳能电池界面电子转移及其飞秒瞬态吸收光谱研究. Acta Physico-Chimica Sinica, 2024, 40(11): 2402006-. doi: 10.3866/PKU.WHXB202402006
-
[15]
Qin Hu , Liuyun Chen , Xinling Xie , Zuzeng Qin , Hongbing Ji , Tongming Su . Ni掺杂构建电子桥及激活MoS2惰性基面增强光催化分解水产氢. Acta Physico-Chimica Sinica, 2024, 40(11): 2406024-. doi: 10.3866/PKU.WHXB202406024
-
[16]
Xiangchun Li , Wei Xue , Xu Liu , Wenyong Lai . Research and Practice on the Cultivation of Innovation Ability of Chemistry Graduate Students in Electronic Information Universities: A Case Study of Nanjing University of Posts and Telecommunications. University Chemistry, 2024, 39(6): 55-62. doi: 10.3866/PKU.DXHX202310018
-
[17]
. . Chinese Journal of Inorganic Chemistry, 2024, 40(11): 0-0.
-
[18]
Tingting Yu , Si Chen , Lianglong Sun , Tongtong Shi , Kai Sun , Xin Wang . Comprehensive Experimental Design for the Photochemical Synthesis, Analysis, and Characterization of Difluoropyrroles. University Chemistry, 2024, 39(11): 196-203. doi: 10.3866/PKU.DXHX202401022
-
[19]
Xinyu Yin , Haiyang Shi , Yu Wang , Xuefei Wang , Ping Wang , Huogen Yu . Spontaneously Improved Adsorption of H2O and Its Intermediates on Electron-Deficient Mn(3+δ)+ for Efficient Photocatalytic H2O2 Production. Acta Physico-Chimica Sinica, 2024, 40(10): 2312007-. doi: 10.3866/PKU.WHXB202312007
-
[20]
Caixia Lin , Zhaojiang Shi , Yi Yu , Jianfeng Yan , Keyin Ye , Yaofeng Yuan . Ideological and Political Design for the Electrochemical Synthesis of Benzoxathiazine Dioxide Experiment. University Chemistry, 2024, 39(2): 61-66. doi: 10.3866/PKU.DXHX202309005
-
[1]
Metrics
- PDF Downloads(1449)
- Abstract views(2699)
- HTML views(73)