Citation: Qian Cunwei, Zang Shiyu, Zhou Qian, Wang Dong, Li Wanxin, Wang Maoyuan. One-Pot Synthesis and Optical Properties of 2, 5-Diphenylthiophene Derivatives[J]. Chinese Journal of Organic Chemistry, ;2017, 37(7): 1781-1786. doi: 10.6023/cjoc201612045 shu

One-Pot Synthesis and Optical Properties of 2, 5-Diphenylthiophene Derivatives

  • Corresponding author: Qian Cunwei, qiancunwei@163.com Wang Maoyuan, 
  • Received Date: 15 December 2016
    Revised Date: 22 February 2017
    Available Online: 8 July 2017

    Fund Project: Natural Science Foundation of the Jiangsu Higher Education Institutions 14JKD150009Project supported by the Natural Science Foundation of the Jiangsu Higher Education Institutions (No. 14JKD150009) and the Excellent Specialties Program Development of Jiangsu Higher Education Institutions

Figures(5)

  • The paper describes a convenient and facile methodology for the synthesis of 2, 5-diphenylthiophene derivatives. The environmentally friendly synthetic approach is supported by a one-pot tandem reaction process. All of the target products was confirmed by 1H NMR, 13C NMR and HRMS. On this basis, UV and fluorescence properties of the synthesized compounds were further explored. The experimental results showed that the UV maximum absorption wavelengths of the compounds are between 292 and 341 nm. The fluorescence spectra showed that these compounds have good fluorescence. The fluorescence emission wavelengths measured in methanol are between 386 and 454.5 nm, and the fluorescence emission wavelengths measured in dichloromethane are between 390 and 412 nm. The increase of conjugation system led to the red shift of fluorescence.
  • 加载中
    1. [1]

      For selected review, see:(a) Wu, X. F.; Neumann, H.; Beller, M. Chem. Rev. 2013, 113, 1.
      (b) Zeni, G.; Larock, R. C. Chem. Rev. 2006, 106, 4644.
      (c) Lipshutz, B. H. Chem. Rev. 1986, 86, 795.
      (d) Lu, H.; Liu, G. T. Planta Med. 1992, 58, 311.
      (e) Navarro, E.; Alonso, S. J.; Trujillo, J.; Jorge, E.; Pérez, C. J. Nat. Prod. 2001, 64, 134.
      (f) Cacchi, S.; Fabrizi, G.; Goggiamani, A. Org. Biomol. Chem. 2011, 9, 641.
      (g) Flynn, B. L.; Hamel, E.; Jung, M. K. J. Med. Chem. 2002, 45, 2670.
      (h) Palkowitz, A. D.; Glasebrook, A. L.; Thrasher, K. J.; Hauser, K. L.; Short, L. L.; Philips, D. L.; Muehl, B. S.; Sato, M.; Shetler, P. K.; Cullinan, G. J.; Pell, T. R.; Bryant, H. U. J. Med. Chem. 1997, 40, 1407.
      (i) Tsuji, H.; Cantagrel, G.; Ueda, Y.; Chen, T.; Wan, L. J.; Nakamura, E. Chem. Asian J. 2013, 8, 2377.

    2. [2]

      Joule, J. A.; Mills, K. Heterocyclic Chemistry, Trans. by You, Y.-C.; Gao, D.-B. Science Press, Beijing, 2004, p. 324(in Chinese).

    3. [3]

      (a) Snégaroff, K.; Komagawa, S.; Chevallier, F.; Gros, P. C.; Golhen, S.; Roisnel, T.; Uchiyama, M.; Mongin, F. Chem.-Eur. J. 2010, 16, 8191.
      (b) Kel'in, A. V.; Gevorgyan, V. J. Org. Chem. 2002, 67, 95.
      (c) Rao, H. S. P.; Jothilingam, S. J. Org. Chem. 2003, 68, 5392.
      (d) Aponick, A.; Li, C. Y.; Malinge, J.; Marques, E. F. Org. Lett. 2009, 11, 4624.
      (e) Egi, M.; Azechi, K.; Akai, S. Org. Lett. 2009, 11, 5002.
      (f) Dheur, J.; Sauthier, M.; Castanet, Y.; Mortreux, A. Adv. Synth. Catal. 2010, 352, 557.

    4. [4]

      (a) Sun, H.; Wu, X.; Hua, R. Tetrahedron Lett. 2011, 52, 4408.
      (b) Singha, R.; Nandi, S.; Ray, J. K. Tetrahedron Lett. 2012, 53, 6531.
      (c) Pridmore, S. J.; Slatford, P. A.; Williams, J. M. J. Tetrahedron Lett. 2007, 48, 5111.
      (d) Kramer, S.; Madsen, J. L. H.; Rottl€ander, M.; Skrydstrup, T. Org. Lett. 2010, 12, 2758.
      (e) Nun, P.; Dupuy, S.; Gaillard, S.; Poater, A.; Cavallod, L.; Nolan, S. P. Catal. Sci. Technol. 2011, 1, 58.
      (f) Jiang, H.; Zeng, W.; Li, Y.; Wu, W.; Huang, L.; Fu, W. J. Org. Chem. 2012, 77, 5179.
      (g) Zheng, Q.; Hua, R.; Yin, T. Curr. Org. Synth. 2013, 10, 161.
      (h) Beny, J.-P.; Dhawan, S. N.; Kagan, J.; Sundlass, S. J. Org. Chem. 1982, 47, 2201.
      (i) Pridmore, S. J.; Slatford, P. A.; Daniel, A.; Whittlesey, M. K.; Williams, J. M. J. Tetrahedron Lett. 2007, 48, 5115.
      (j) Lavallo, V.; Frey, G. D.; Donnadieu, B.; Soleilhavoup, M.; Bertrand, G. Angew. Chem., Int. Ed. 2008, 47, 5224.
      (k) Zheng, Q.; Hua, R. Tetrahedron Lett. 2010, 51, 4512.
      (l) Mandadapu, A. K.; Sharma, S. K.; Gupta, S.; Krishna, D. G. V.; Kundu, B. Org. Lett. 2011, 13, 3162.
      (m) Mandadapu, A. K.; Dathi, M. D.; Arigela, R. K.; Kundu, B. Tetrahedron 2012, 68, 8207.
      (n)Wang, L.; Yu, X.; Feng, X.; Bao, M. Org. Lett. 2012, 14, 2418.
      (o) Zheng, Q.; Hua, R.; Yin, T. Curr. Org. Synth. 2013, 10, 161.
      (p) Jiang, H.; Zeng, W.; Li, Y.; Wu, W.; Huang, L.; Fu, W. J. Org. Chem. 2012, 77, 5179.

    5. [5]

      (a) Zheng, Q.; Hua, R.; Jiang, J.; Zhang, L. Tetrahedron 2014, 70, 8252.
      (b) Zhang, G.; Yi, H.; Chen, H.; Bian, C.; Liu, C.; Lei, A. Org. Lett. 2014, 16, 6156.
      (c) Tang, J.; Zhao, X. RSC Adv. 2012, 2, 5488.

    6. [6]

      (a) Li, D.; Yin, K.; Li, J.; Jia, X. Tetrahedron Lett. 2008, 49, 5918.
      (b) Li, L.; Wang, J.; Zhang, G.; Liu, Q. Tetrahedron Lett. 2009, 50, 4033.

    7. [7]

      Urselmann, D.; Antovic, D.; Müller T. Beilstein J. Org. Chem. 2011, 7, 1499.  doi: 10.3762/bjoc.7.174

    8. [8]

      Irudayanathan, F. M.; Raja, G. C. E.; Lee, S. Tetrahedron 2015, 71, 4418.  doi: 10.1016/j.tet.2015.05.017

  • 加载中
    1. [1]

      Yinuo Wang Siran Wang Yilong Zhao Dazhen Xu . Selective Synthesis of Diarylmethyl Anilines and Triarylmethanes via Multicomponent Reactions: Introduce a Comprehensive Experiment of Organic Chemistry. University Chemistry, 2024, 39(8): 324-330. doi: 10.3866/PKU.DXHX202401063

    2. [2]

      Zhongyan Cao Shengnan Jin Yuxia Wang Yiyi Chen Xianqiang Kong Yuanqing Xu . Advances in Highly Selective Reactions Involving Phenol Derivatives as Aryl Radical Precursors. University Chemistry, 2025, 40(4): 245-252. doi: 10.12461/PKU.DXHX202405186

    3. [3]

      Zhiwen HUANGQi LIUJianping LANG . W/Cu/S cluster-based supramolecular macrocycles and their third-order nonlinear optical responses. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 79-87. doi: 10.11862/CJIC.20240184

    4. [4]

      Yikai Wang Xiaolin Jiang Haoming Song Nan Wei Yifan Wang Xinjun Xu Cuihong Li Hao Lu Yahui Liu Zhishan Bo . 氰基修饰的苝二酰亚胺衍生物作为膜厚不敏感型阴极界面材料用于高效有机太阳能电池. Acta Physico-Chimica Sinica, 2025, 41(3): 2406007-. doi: 10.3866/PKU.WHXB202406007

    5. [5]

      Yonghui ZHOURujun HUANGDongchao YAOAiwei ZHANGYuhang SUNZhujun CHENBaisong ZHUYouxuan 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

    6. [6]

      Shenhao QIUQingquan XIAOHuazhu TANGQuan XIE . First-principles study on electronic structure, optical and magnetic properties of rare earth elements X (X=Sc, Y, La, Ce, Eu) doped with two-dimensional GaSe. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2250-2258. doi: 10.11862/CJIC.20240104

    7. [7]

      Zhihao HEJiafu DINGYunjie WANGXin SU . First-principles study on the structure-property relationship of AlX and InX (X=N, P, As, Sb). Chinese Journal of Inorganic Chemistry, 2025, 41(5): 1007-1019. doi: 10.11862/CJIC.20240390

    8. [8]

      Jinyao Du Xingchao Zang Ningning Xu Yongjun Liu Weisi Guo . Electrochemical Thiocyanation of 4-Bromoethylbenzene. University Chemistry, 2024, 39(6): 312-317. doi: 10.3866/PKU.DXHX202310039

    9. [9]

      Jianfeng Yan Yating Xiao Xin Zuo Caixia Lin Yaofeng Yuan . Comprehensive Chemistry Experimental Design of Ferrocenylphenyl Derivatives. University Chemistry, 2024, 39(4): 329-337. doi: 10.3866/PKU.DXHX202310005

    10. [10]

      Yukun Chang Haoqin Huang Baolei Wang . Preparation of Trans-Cinnamic Acid via “One-Pot” Protocol of Aldol Condensation-Hydrolysis Reaction: Recommending an Improved Organic Synthesis Experiment. University Chemistry, 2024, 39(4): 322-328. doi: 10.3866/PKU.DXHX202309095

    11. [11]

      Zhen Yao Bing Lin Youping Tian Tao Li Wenhui Zhang Xiongwei Liu Wude Yang . Visible-Light-Mediated One-Pot Synthesis of Secondary Amines and Mechanistic Exploration. University Chemistry, 2024, 39(5): 201-208. doi: 10.3866/PKU.DXHX202311033

    12. [12]

      Renxiao Liang Zhe Zhong Zhangling Jin Lijuan Shi Yixia Jia . A Palladium/Chiral Phosphoric Acid Relay Catalysis for the One-Pot Three-Step Synthesis of Chiral Tetrahydroquinoline. University Chemistry, 2024, 39(5): 209-217. doi: 10.3866/PKU.DXHX202311024

    13. [13]

      Dongheng WANGSi LIShuangquan ZANG . Construction of chiral alkynyl silver chains and modulation of chiral optical properties. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 131-140. doi: 10.11862/CJIC.20240379

    14. [14]

      Xiao SANGQi LIUJianping 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

    15. [15]

      Hongjie SHENHaozhe MIAOYuhe YANGYinghua LIDeguang HUANGXiaofeng ZHANG . Synthesis, crystal structure, and fluorescence properties of two Cu(Ⅰ) complexes based on pyridyl ligand. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 855-863. doi: 10.11862/CJIC.20250009

    16. [16]

      Peng ZHOUXiao CAIQingxiang MAXu LIU . Effects of Cu doping on the structure and optical properties of Au11(dppf)4Cl2 nanocluster. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1254-1260. doi: 10.11862/CJIC.20240047

    17. [17]

      Xin MAYa SUNNa SUNQian KANGJiajia ZHANGRuitao ZHUXiaoli GAO . A Tb2 complex based on polydentate Schiff base: Crystal structure, fluorescence properties, and biological activity. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1347-1356. doi: 10.11862/CJIC.20230357

    18. [18]

      Wenjie SHIFan LUMengwei CHENJin WANGYingfeng HAN . Synthesis and host-guest properties of imidazolium-functionalized zirconium metal-organic cage. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 105-113. doi: 10.11862/CJIC.20240360

    19. [19]

      Laiying Zhang Yinghuan Wu Yazi Yu Yecheng Xu Haojie Zhang Weitai Wu . Innovation and Practice of Polymer Chemistry Experiment Teaching for Non-Polymer Major Students of Chemistry: Taking the Synthesis, Solution Property, Optical Performance and Application of Thermo-Sensitive Polymers as an Example. University Chemistry, 2024, 39(4): 213-220. doi: 10.3866/PKU.DXHX202310126

    20. [20]

      Yiming Liang Ziyan Pan Kin Shing Chan . One Drink, Two Tears in the Central Nervous System: The Perils of Disulfiram-Like Reactions. University Chemistry, 2025, 40(4): 322-325. doi: 10.12461/PKU.DXHX202406016

Metrics
  • PDF Downloads(0)
  • Abstract views(1406)
  • HTML views(180)

通讯作者: 陈斌, bchen63@163.com
  • 1. 

    沈阳化工大学材料科学与工程学院 沈阳 110142

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索
Address:Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888
Powered By info@rhhz.net

/

DownLoad:  Full-Size Img  PowerPoint
Return