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Chinese Journal of Organic Chemistry >

2012 , Vol. 32 >Issue 04: 714 - 718

DOI: https://doi.org/10.6023/cjoc1110251

Articles

Synthesis, Properties and Quantum Chemical Calculation of 3-(4,5-Dibenzyldithio-1,3-dithiol-2-ylidene)naphthopyranone

  • Zhu Yulan ,
  • Xia Ke ,
  • Zhou Xinxin ,
  • Cao Li ,
  • Lu Mingzhu ,
  • Wang Kun
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  • a Jiangsu Key Laboratory for Chemistry of Low-dimensional Materials, School of Chemistry and Chemical Engineering, Huaiyin Normal University, Huai'an 223300;
    b School of Chemistry, Northeast Normal University, Changchun 130024;
    c School of Biological and Chemical Engineering, Jiangsu Food Science College, Huai′an 223003

Received date: 2011-10-25

  Revised date: 2011-11-29

  Online published: 2012-04-24

Supported by

Project supported by the National Natural Science Foundation of China (No. 20671038) and the Natural Science Foundation of Jiangsu Province (No. BK2011408).

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Abstract

A new 3-(4,5-dibenzyldithio-1,3-dithiol-2-ylidene)naphthopyranone (3) has been synthesized. The molecular structure was identified and characterized by UV-Vis, 1H NMR, 13C NMR, IR and TOFMS techniques. The electronic spectra, thermostability and fluorescence spectroscopy of 3 were briefly studied. The geometric structure of the product was optimized using Gaussian 03 quantum chemical program package with the method of density functional theory (DFT) at the B3PW91 level. The calculating results are in agreement with the experimental values. The research shows that 3 displays an intramolecular charge-transfer transition and remarkable fluorescence properies which were instructive explorations for pursuing new luminescent materials.

Key words： synthesis; charge transfer; absorption spectra; fluorescent property; density functional theory

Cite this article

Zhu Yulan , Xia Ke , Zhou Xinxin , Cao Li , Lu Mingzhu , Wang Kun . Synthesis, Properties and Quantum Chemical Calculation of 3-(4,5-Dibenzyldithio-1,3-dithiol-2-ylidene)naphthopyranone[J]. Chinese Journal of Organic Chemistry, 2012 , 32(04) : 714 -718 . DOI: 10.6023/cjoc1110251

References

[1] Xiao, Y.; Qian, X. H. Tetrahedron Lett. 2003, 44(10), 2087.  

[2] Zhao, T. F.; Zhao, D. F.; Chang, Y. W. Dye Ind. 1998, 35(3), 1 (in Chinese). (赵同丰, 赵德丰, 常玉威, 染料工业, 1998, 35(3), 1.)  

[3] Kollár, J.; Hrdlovi?, P.; Chmela, ?.; Sarakha, M.; Guyot, G. J. Photochem. Photobiol. A 2005, 170(2),151.

[4] Georgiev, N. I.; Bojinov, V. B.; Nikolov, P. S. Dyes Pigm. 2011, 88, 350.  

[5] Kobayashi, H.; Cui, H. B.; Kobayashi, A. Chem. Rev. 2004, 104, 5265.  

[6] Li, X. H.; Zhang, G. X.; Ma, H. M.; Zhang, D. Q.; Li, J.; Zhu, D. B. J. Am. Chem. Soc. 2004, 126, 11543.  

[7] Herranz, M.; Martín, N.; Ramey, J.; Guldi, D. M. Chem. Commun. 2002, 24, 2968.

[8] Zhu, Y. L.; Zhou, X. X.; Yin, Q. F.; Cao, L. Chin. J. Org. Chem. 2009, 29, 34 (in Chinese). (朱玉兰, 周鑫鑫, 尹起范, 曹丽, 有机化学, 2009, 29, 34.)

[9] Christensen, C. A.; Batsanov, A. S.; Bryce, M. R. J. Am. Chem. Soc. 2006, 128, 10484.  

[10] Zhu, Y. L.; Tian, L. B.; Ma, K. R.; Kan, Y. H.; Tang, X. L.; Hu, H. Y. Solid State Sci. 2010, 12, 391.  

[11] Zhao, B. T.; Wu, S. J.; Ye, B. X. Chin. J. Org. Chem. 2011, 31, 1027 (in Chinese). (赵邦屯, 吴圣江, 冶保献, 有机化学, 2011, 31, 1027.)

[12] Leary, E.; Higgins, S. J.; Zalinge, H. V.; Haiss, W.; Nichols, R. J.; Nygaard, S.; Jeppesen, J. O.; Ulstrup, J. J. Am. Chem. Soc. 2008, 130, 12204.  

[13] Wenger, S.; Bouit, P. A.; Chen, Q. L.; Teuscher, J.; Censo, D. D.; Humphry-Baker, R.; Moser, J. E.; Delgado, J. L.; Martin, N.; Zakeeruddin, S. M.; Gr?tzel, M. J. Am. Chem. Soc. 2010, 132, 5164.  

[14] Zhu, Y. L.; Kan, Y. H.; Lin, Y. K.; Pan, W. L.; Su, Z. M.; Cui, H. B. Acta Chim. Sinica 2003, 61, 19160 (in Chinese). (朱玉兰, 阚玉和, 林元奎, 潘万龙, 苏忠民, 崔亨波, 化学学报, 2003, 61, 19160.)

[15] Zhang, G. X.; Zhang, D. Q.; Yin, S. W.; Yang, X. D.; Shuai, Z. G.; Zhu, D. B. Chem. Commun. 2005, 2161.  

[16] Dolder, S.; Liu, S. X.; Derf, F. L.; Sallè, M.; Neels, A.; Decurtins, S. Org. Lett. 2007, 9, 3753.  

[17] Liu, Y.; Qiu, Y. Q.; Sun, S. L.; Zhao, H. B.; Su, Z. M. Acta Chim. Sinica 2010, 68, 1443 (in Chinese). (刘艳, 仇永清, 孙世玲, 赵海波, 苏忠民, 化学学报, 2010, 68, 1443.)

[18] Steimecke, H. G.; Sieler, J.; Kirsme, R.; Hoyer, E. Phosphorous Sulfur 1979, 7, 49.  

[19] Liu, Y. C.; Yu, T. Y.; Yao, Z. L. Chin. Sci. Bull. 1995, 40, 701 (in Chinese). (刘永成, 于同隐, 姚钟麒, 科学通报, 1995, 40, 701.)

[20] Wang, F.; Ziegler, T. J. Chem. Phys. 2005, 123, 194102.

[21] Zhu, Y. L.; Zhou, S. Y.; Kan,Y. H.; Yan, L. K.; Su, Z. M. J. Chem. Phys. 2007, 126, 245106.

[22] Zhu, Y. L.; Zhou, S. Y.; Kan,Y. H.; Su, Z. M. J. Organomet. Chem. 2009, 694, 3012.  

[23] Qin, C. S.; Yang, G. C.; Zhao, L.; Sun, S. L.; Qiu, Y. Q.; Su, Z. M.; Zhu, Y. L. Synth. Met. 2009, 159(21～22), 2406.  
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