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

doi:10.6023/cjoc1110251

Chin. J. Org. Chem. ›› 2012, Vol. 32 ›› Issue (04): 714-718.DOI: 10.6023/cjoc1110251 Previous Articles Next Articles

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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^a,b, 夏克^a, 周鑫鑫^a,c, 曹丽^a,b, 卢明祝^a, 王琨^b

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 发布日期:2012-04-24
通讯作者: 朱玉兰 E-mail:ylzhu1998@126.com
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.

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

Zhu Yulan^a,b, Xia Ke^a, Zhou Xinxin^a,c, Cao Li^a,b, Lu Mingzhu^a, Wang Kun^b

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:2011-10-25 Revised:2011-11-29 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).

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]. Chin. J. Org. Chem., 2012, 32(04): 714-718.

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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

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

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