Synthesis and Photo-electric Properties of 9-[4,5-Bis-(hexadecylthio)-1,3-dithiol-2-ylidene]anthracen-10(9H)-one

Chin. J. Org. Chem. ›› 2010, Vol. 30 ›› Issue (06): 865-870. Previous Articles Next Articles

Full Papers

9-[(4,5-二硫十六烷基)-1,3-二硫环戊烯-2-亚基]-10(9H)-蒽酮的合成及光电性质研究

朱玉兰*^{,1,2，尹起范¹，马奎蓉¹，曹丽¹^{,2，荆晓¹^{,2，仲慧¹}}}

¹淮阴师范学院化学化工学院江苏省低维材料化学重点建设实验室淮安 223300)
(²东北师范大学化学学院长春 130024

收稿日期:2009-08-24 修回日期:2009-11-10 发布日期:2010-01-20
通讯作者: 朱玉兰 E-mail:ylzhu1998@126.com
基金资助:
国家级.国家自然科学基金

Synthesis and Photo-electric Properties of 9-[4,5-Bis-(hexadecylthio)-1,3-dithiol-2-ylidene]anthracen-10(9H)-one

Zhu Yulan*^{,1,2 Yin Qifan¹ Ma Kuirong¹ Cao Li¹^{,2 Jing Xiao¹^{,2 Zhong Hui¹}}}

¹ Jiangsu Key Laboratory for Chemistry of Low-dimensional Materials, School of Chemistry and Chemical Engineering, Huaiyin Normal University, Huaian 223300)
(² School of Chemistry, Northeast Normal University, Changchun 130024)

Received:2009-08-24 Revised:2009-11-10 Published:2010-01-20

Abstract

A new 9-[4,5-bis-(hexadecylthio)-1,3-dithiol-2-ylidene]anthracen-10(9H)-one (d) has been synthesized. The molecular structure was characterized by ¹H NMR, ¹³C NMR, TOFMS and IR spectra. The photocurrent response experiment was performed with the electrochemical workstation. The photocurrent is relatively stable and reversible, which means that this system has an obvious property of photo-electric transfer. The geometry structure of the product was optimized using Gaussian 03 quantum chemical program package, and the method of density functional theory (DFT) at the level of 6-31G(d). The calculated results are in agreement with the experimental values. The research shows that this compound displays an intramolecular charge-transfer property.

Key words: anthraquinone derivative, charge transfer, photo-electric property, DFT

Cite this article

ZHU Yu-Lan, YIN Qi-Fan, MA Kui-Rong, CAO Li, JING Xiao, ZHONG Hui. Synthesis and Photo-electric Properties of 9-[4,5-Bis-(hexadecylthio)-1,3-dithiol-2-ylidene]anthracen-10(9H)-one[J]. Chin. J. Org. Chem., 2010, 30(06): 865-870.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

[1]	Huang Shuaishuai, Nie Yixue, Yang Jingjing, Zheng Zhanjiang, Cao Jian, Xu Zheng, Xu Liwen. Copper-Catalyzed Arylated Etherification of 2,2-Difluoroethanol and Its Mechanistic Study [J]. Chinese Journal of Organic Chemistry, 2020, 40(7): 2018-2025.
[2]	Li Zhifeng, Wang Wenpeng, Wang Xicun, Quan Zhengjun. Mechanism of Synthesis of Phosphinecarboxamides by Reaction of Sodium Phosphaethynolate Anion and Amines under Acid-Free Conditions: Density Functional Theory Investigation [J]. Chinese Journal of Organic Chemistry, 2020, 40(6): 1563-1570.
[3]	Fu Qingqing, Hu Jinghan, Yao Ying, Yin Zhiyuan, Gui Kui, Long Chen, Ni Pengwei. Novel High Sensitivity Dual-Channel Chemosensor for Detecting CN^- Based on Coumarin Derivative in Aqueous Media and Its Application in Food Samples [J]. Chinese Journal of Organic Chemistry, 2020, 40(5): 1232-1238.
[4]	Li Yingjun, Liu Xuejie, Liu Jihong, Gao Lixin, Jin Kun, Sheng Li, Yang Hongjing, Lin Ledi, Li Jia. Synthesis and Protein Tyrosine Phosphatase 1B (PTP1B) Inhibitory Activity Evaluation of Novel Carbazole-Based Carbohydrazone Derivatives [J]. Chinese Journal of Organic Chemistry, 2020, 40(2): 478-488.
[5]	Li Yingjun, Yang Kaidong, Jin Kun, Gao Lixin, Sheng Li, Liu Xuejie, Yang Hongjing, Lin Ledi, Li Jia. Synthesis and Cdc25B/PTP1B Inhibitory Activity Evaluation of Novel Carbazole-Based Mono-/Bis-thiocarbohydrazone Derivatives [J]. Chinese Journal of Organic Chemistry, 2020, 40(1): 162-174.
[6]	Li Yingjun, Zhao Yue, Jin Kun, Gao Lixin, Sheng Li, Liu Xuejie, Yang Hongjing, Lin Ledi, Li Jia. Synthesis and PTP1B/TCPTP Inhibitory Activity Evaluation of Novel 2,5-Disubstituted-1,3,4-thiadiazolamide Derivatives Containing Carbazole/Benzimidazole Moity [J]. Chin. J. Org. Chem., 2019, 39(9): 2599-2608.
[7]	Chang Yongxina, Li Baia, Gao Yunfana, Xu Kuoxi. A Novel Schiff-Base Fluorescent Probe for Cr³⁺ and Its Bioimaging in Cells [J]. Chin. J. Org. Chem., 2019, 39(4): 1023-1028.
[8]	Wang Kaixuan, Wang Lanzhi. Unexpected Rearrangement Reaction and Synthesis of Benzoxazoles [J]. Chin. J. Org. Chem., 2019, 39(4): 1147-1152.
[9]	Zhang Shilong, Jiang Lasheng. Supramolecular Assembly Based on the Novel Sail-Boat-Shaped Self-Complexes [J]. Chin. J. Org. Chem., 2019, 39(3): 720-726.
[10]	Sun Yuewei, Zhou Laiyun, Wang Lanzhi. A Domino Reaction for the Selective Synthesis of Functionalized Benzo[b] [1,4]diazepines [J]. Chinese Journal of Organic Chemistry, 2019, 39(12): 3516-3523.
[11]	Cheng Xiaohong, Xu Ke, Qu Shaohua, Ruan Zhijun. Ratiometric Fluorescent Probe for Homocysteine and CysteineBased on the Aldehyde Functionalized Coumarin and SuccessfulBioimaging Application [J]. Chinese Journal of Organic Chemistry, 2019, 39(10): 2835-2842.
[12]	Bian Rongjian, Bao Xiaoguang. Computational Insights into the Mechanism of Pd(0) and Ben-zoic Acid Co-Catalyzed Hydroamination of Internal Alkynes [J]. Chin. J. Org. Chem., 2017, 37(1): 190-195.
[13]	Zheng Yueyou, Xie Qionglin, Wang Bingxi. Synthesis and Photophysical and Electrochemical Properties of 10-Methyl-10H-phenothiazine-5,5-dioxide Derivatives [J]. Chin. J. Org. Chem., 2016, 36(4): 803-811.
[14]	Feng JunShao, Jiangyang, Gong Zhongliang, Zhong Yuwu. Amine-Amine Electronic Coupling through an Anthracene Bridge [J]. Chin. J. Org. Chem., 2016, 36(10): 2407-2412.
[15]	Du Lijuan, Wu Caihong, Gu Honghong, Li Juan. A Density Functional Theory Study of the Mechanism of Cu(II)-Catalyzed Synthesis of Pyrido[1,2-a]benzimidazoles [J]. Chin. J. Org. Chem., 2015, 35(8): 1726-1732.

9-[(4,5-二硫十六烷基)-1,3-二硫环戊烯-2-亚基]-10(9H)-蒽酮的合成及光电性质研究

Synthesis and Photo-electric Properties of 9-[4,5-Bis-(hexadecylthio)-1,3-dithiol-2-ylidene]anthracen-10(9H)-one

PDF

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments