SIOC English
有机化学
高级检索

有机化学 >

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

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

研究论文

3-(4,5-二苄硫基-1,3-二硫杂环戊烯-2-亚基)萘吡喃酮的合成、性质及量子化学计算

  • 朱玉兰 ,
  • 夏克 ,
  • 周鑫鑫 ,
  • 曹丽 ,
  • 卢明祝 ,
  • 王琨
展开
  • a 江苏省低维材料化学重点建设实验室 淮阴师范学院化学化工学院 淮安 223300;
    b 东北师范大学化学学院 长春 130024;
    c 江苏食品职业技术学院化学与生物工程学院 淮安 223003

收稿日期: 2011-10-25

  修回日期: 2011-11-29

  网络出版日期: 2012-04-24

基金资助

国家自然科学基金(No. 20671038)和江苏省自然科学基金(No. BK2011408)资助项目.

收起

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
Expand
  • 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).

Fold

摘要

设计合成了一种新的具有D-π-A 体系的有机分子: 3-(4,5-二苄硫基-1,3-二硫杂环戊烯-2-亚基)萘吡喃酮, 通过UV-vis, 1H NMR, 13C NMR, TOFMS 和IR 确定了其结构. 初步研究了该化合物的电子光谱、荧光光谱和热稳定性. 运用Gaussian 03 量子化学程序包, 采用密度泛函(DFT) B3PW91 的方法优化了其基态几何结构, 得到的几何参数与实验结果吻合得很好. 研究结果表明, 体系中存在着分子内的电荷转移, 有较好的荧光性质, 为寻找新的发光材料具有一定的实际意义.

关键词： 合成; 电荷转移; 吸收光谱; 荧光性质; 密度泛函

本文引用格式

朱玉兰 , 夏克 , 周鑫鑫 , 曹丽 , 卢明祝 , 王琨 . 3-(4,5-二苄硫基-1,3-二硫杂环戊烯-2-亚基)萘吡喃酮的合成、性质及量子化学计算[J]. 有机化学, 2012 , 32(04) : 714 -718 . DOI: 10.6023/cjoc1110251

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

参考文献

[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.  
Options
文章导航

/

〈 〉