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

Yancheng Teachers College, School of Chemical & Environmental Engineering, Yancheng 224051

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

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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.
- aryl acetylene,
- urinary sulfur,
- thiophene derivative,
- one-pot synthesis,
- optical properties
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
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