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

doi:10.6023/cjoc201612045

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (7): 1781-1786.DOI: 10.6023/cjoc201612045 Previous Articles Next Articles

Articles

2,5-二取代噻吩衍生物的“一锅化”串联合成及光学性质

钱存卫, 臧世宇, 周倩, 王栋, 李万鑫, 王茂元

盐城师范学院化学与环境工程学院盐城 224051

收稿日期:2016-12-15 修回日期:2017-02-22 发布日期:2017-03-08
通讯作者: 钱存卫 E-mail:qiancunwei@163.com
基金资助:
江苏省高校自然科学基金（No.14JKD150009）、江苏高校品牌专业建设工程资助项目.

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

Qian Cunwei, Zang Shiyu, Zhou Qian, Wang Dong, Li Wanxin, Wang Maoyuan

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

Received:2016-12-15 Revised:2017-02-22 Published:2017-03-08
Contact: 10.6023/cjoc201612045 E-mail:qiancunwei@163.com
Supported by:
Project 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.

1. One-Pot Synthesis and Optical Properties of 2,5-Diphenylthiophene Derivatives.PDF(945KB)

Abstract

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.

Key words: aryl acetylene, urinary sulfur, thiophene derivative, one-pot synthesis, optical properties

Cite this article

Qian Cunwei, Zang Shiyu, Zhou Qian, Wang Dong, Li Wanxin, Wang Maoyuan. One-Pot Synthesis and Optical Properties of 2,5-Diphenylthiophene Derivatives[J]. Chin. J. Org. Chem., 2017, 37(7): 1781-1786.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[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] Joule, J. A.; Mills, K. Heterocyclic Chemistry, Trans. by You, Y.-C.; Gao, D.-B. Science Press, Beijing, 2004, p. 324(in Chinese). (J. A. 焦耳, K. 米尔斯, 杂环化学, 由业诚, 方大彬译, 科学出版社, 北京, 2004, p. 324.)
[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] (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] (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] (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] Urselmann, D.; Antovic, D.; Müller T. Beilstein J. Org. Chem. 2011, 7, 1499.
[8] Irudayanathan, F. M.; Raja, G. C. E.; Lee, S. Tetrahedron 2015, 71, 4418.

[1]	Wensheng Zhang, Yan Li, Haiyan Cui, Xiaoli Su, Supeng Xu. One-Pot Synthesis of N-Substituted Isoindolin-1-ones via Reductive Amination/Lactamization of Methyl 2-Formylbenzoate [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2456-2461.
[2]	Xianghao Luo, Yibi Xie, Nianyu Huang, Long Wang. Ugi Four-Component Reaction Based on in-situ Capture of Isocyanide and Post-Modification Tandem Reaction: One-Pot Synthesis of Nitrogen Heterocycles [J]. Chinese Journal of Organic Chemistry, 2022, 42(3): 838-846.
[3]	Jinni Liu, Yibi Xie, Qingqing Yang, Nianyu Huang, Long Wang. Ugi Four-Component Reaction Based on the in situ Capture of Amines and Subsequent Modification Tandem Cyclization Reaction: "One-Pot" Synthesis of Six- and Seven-Membered Heterocycles [J]. Chinese Journal of Organic Chemistry, 2021, 41(6): 2374-2383.
[4]	He Shuwang, Yan Shiqiang, Guo Wei, Zhai Guangxi, Zhang Wei. One-Pot Synthesis of Amino Alcohols from Styrenes [J]. Chinese Journal of Organic Chemistry, 2020, 40(7): 2094-2098.
[5]	Lan Jin, Xie Zongbo, Yang Jiangnan, Meng Jia, Liu Yishuai, Le Zhanggao. One-Pot Multi-component Synthesis of N,O-Acetal Compounds Catalyzed by D-Proline at Room Temperature [J]. Chinese Journal of Organic Chemistry, 2020, 40(5): 1331-1336.
[6]	Jia Jiru, Yu Aimin, Liu Xuguang, Meng Xiangtai. 1,4-Diazabicyclo[2.2.2]octane (DABCO)-Catalyzed [4+2] Domino Reaction of Allenoates: Synthesis of Benzo[4,5]thieno-[3,2-b]pyran Derivatives [J]. Chin. J. Org. Chem., 2019, 39(8): 2175-2182.
[7]	Wan Linxi, Gao Feng, Chen Wei, Zhou Xianli. One-Pot Synthesis of 2-((2-Aminobenzoyl)amino)benzoic Acid Derivatives [J]. Chin. J. Org. Chem., 2019, 39(8): 2270-2276.
[8]	Liang Jie, Ma Huifang, Ablajan Keyume. High-Selective One-Pot Synthesis of Spirocyclopropane Pyrazolones Promoted by 4-Dimethylaminopyridine [J]. Chinese Journal of Organic Chemistry, 2019, 39(11): 3169-3175.
[9]	Sun Xiaoli, Sun Zhenhua, Han Minmin, Han Jing, He Weimin, Chen Jie, Deng Hongmei, Shao Min, Zhang Hui, Cao Weiguo. Synthesis of Perfluoroalkylated Fluorenes with Phosphonate Group via One-Pot Synthesis Process [J]. Chin. J. Org. Chem., 2019, 39(1): 192-199.
[10]	Bai Feicheng, Hu Deqing, Liu Yunyun, Wei Li. One-Pot and Multicomponent Synthesis of N-Substituted-4-hydroxyl-2-pyridones [J]. Chin. J. Org. Chem., 2018, 38(8): 2054-2059.
[11]	Chen Jinyang, Wu Xiaobo, Yi Rongnan, Xu Xinxua. Nickel-Catalyzed Coupling of Grignard Reagents and Diaryl Acetylenes for Synthesis of Tetra-substituted Naphthalenes [J]. Chin. J. Org. Chem., 2017, 37(7): 1850-1854.
[12]	Xu Dingjian, Meng Lichen, Xu Hang, Yao Xiaoquan. Ligand-Triggered, Copper Catalyzed Synthesis of Peresters and Allylic Ester from Aldehydes [J]. Chin. J. Org. Chem., 2017, 37(5): 1205-1212.
[13]	Xing Xuejian, Fan Kui, Pang Haixia, Wu Yang, Yang Jinghui, Shi Wei, Xie Zhengfeng, Hui Yonghai. One-Pot Synthesis of 4-Thiazolidinone Derivatives Catalyzed by Zinc Acetate-Schiff Base Complex Immobilized on Mesoporous Molecular Sieve MCM-41 [J]. Chin. J. Org. Chem., 2016, 36(8): 1942-1947.
[14]	Yu Zutao, Wang Zeyu, Wu Xiao, Hu Gaoyun, Li Qianbin. “One-Pot” Synthesis of 1-Phenyl-1H-benzimidazole Derivatives Facilitated by Fe [J]. Chin. J. Org. Chem., 2016, 36(7): 1672-1676.
[15]	Li Yibiao, Cheng Liang, Chen Lu, Li Bin, Sun Ning, Qing Ning. One-Pot Synthesis of Substituted Thiophene and Furan Derivatives from Terminal Alkynes [J]. Chin. J. Org. Chem., 2016, 36(10): 2426-2436.

2,5-二取代噻吩衍生物的“一锅化”串联合成及光学性质

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

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments