Synthesis and Properties of a Novel Spirooxazine Dye

doi:10.6023/cjoc201308040

Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (4): 804-808.DOI: 10.6023/cjoc201308040 Previous Articles Next Articles

Articles

含肉桂酸酯基螺噁嗪的合成及性质研究

杨素华^a, 闫素君^b, 郇玲^a

a 赤峰学院化学化工学院赤峰 024000;
b 中山大学化学化工学院广州 510275

收稿日期:2013-08-31 修回日期:2013-11-10 发布日期:2013-12-06
通讯作者: 杨素华 E-mail:cfyangsuhua@126.com
基金资助:
内蒙古自治区高等学校科学研究基金（No. NJ10244）资助项目

Synthesis and Properties of a Novel Spirooxazine Dye

Yang Suhua^a, Yan Sujun^b, Huan Ling^a

a School of Chemistry and Chemical Engineering, Chifeng College, Chifeng 024000;
b School of Chemistry and Chemical Engineering, Sun Yat-Sen University, Guangzhou 510275

Received:2013-08-31 Revised:2013-11-10 Published:2013-12-06
Supported by:
Project supported by the Research Program of Science at Universities of Inner Mongolia Autonomous Region (No. NJ10244).

A novel bifunctional photochromic compound 2 based on spirooxazine and cinnamoyl moiety was synthesized by esterification reaction. Its structure was characterized by ¹H NMR, ¹³C NMR, IR and X-ray single crystal diffraction. The compound was proved by UV testing to have excellent photochromic properties both in organic solvents and polymer films when irridiated with high pressure Hg lamp. The acidichromism phenomenon of compound 2 was studied too. No significant fluorescence emission of compound 2 was observed in EtOH solution before and after irradiation. Under the acidic condition or irradiation with 150 W Xe lamp, The ethanol solution of compound 2 exhibits a good fluorescence respectively. The ethanol solution of compound 2 exhibits obvious fluorescence emission. After irradiating the acidic solution, new fluorescence emission can be observed. The emission change modulated by acid or light offers compound 2 to be potential as a new fluorescent molecular switch.

Key words: spirooxazine, photochromism, cinnamate, acidichromism, fluorescence

Cite this article

Yang Suhua, Yan Sujun, Huan Ling. Synthesis and Properties of a Novel Spirooxazine Dye[J]. Chin. J. Org. Chem., 2014, 34(4): 804-808.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

[1]	Simin Wu, Jiaxin Tang, Yujia Zhou, Xuetao Xu, Haoxing Zhang, Shaohua Wang. α-Glucosidase Inhibition Research of Derivatives Based on 2β-Acetoxyferruginol Scaffold Excluding Acetic Acid Group [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 613-621.
[2]	Cuiyun Ma, Hailan Luo, Fuhua Zhang, Dan Guo, Shuxing Chen, Fei Wang. Green Biosynthesis, Photophysical Properties and Application of 3-Pyrrolyl BODIPY [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 216-223.
[3]	Weiqing Yang, Yanbing Ge, Yuanyuan Chen, Ping Liu, Haiyan Fu, Menglin Ma. Design and Synthesis of Fluorescent 1,8-Napthalimide Derivatives and Their Identification of Cysteine [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 180-194.
[4]	Yi Zhang, Cheng-Zhuo Du, Ji-Kun Li, Xiao-Ye Wang. Recent Advances in Multi-Resonance Thermally Activated Delayed Fluorescence Materials Based on B,N-Heteroarenes [J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1645-1690.
[5]	Kaichun Liang, Keyan Bai, Lei Dai, Yuan Liu, Zecong Ye, Yanping Huo. Design, Synthesis and Electroluminescent Properties of Multiresonant Thermally Activated Delayed Fluorescence Materials Based on Tetrahydroquinoline [J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1799-1807.
[6]	Xiaodong Yang, Xiaokang Zheng, Hailiang Dong, Jing Sun, Hua Wang. Research Progress of Circularly Polarized Thermally Activated Delayed Fluorescence Materials and Devices [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1292-1309.
[7]	Wu Zhou, Min Peng, Qingxiang Liang, Aibin Wu, Wenming Shu, Weichu Yu. A Novel Turn-On Fluorescent Probe Based on Naphthalimide for Highly Selective and Sensitive Detection of Hydrogen Sulfide in Solution and Gas [J]. Chinese Journal of Organic Chemistry, 2023, 43(12): 4277-4283.
[8]	Yuehua Zhang, Fei Nie, Lu Zhou, Xiaofeng Wang, Yuan Liu, Yanping Huo, Wencheng Chen, Zujin Zhao. Synthesis and Optoelectronic Studies of Thermally Activated Delayed Fluorescence Materials Based on Benzothiazolyl Ketones [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3876-3887.
[9]	Xiaoyang Xu, Meiyan Liu, Chenglong Li, Xiaoming Wu, Xuguang Liu. Recent Advance of 1,4-BN Heteroaromatics in China [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3826-3843.
[10]	Jianwen Qiu, Meng Liu, Xinyi Xiong, Yong Gao, Hu Zhu. Research Progress in High Brightness Near Infrared Fluorescent Dyes [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3745-3760.
[11]	Yaxin Yang, Lin Chen, Xiaoling Hu, Keli Zhong, Shidi Li, Xiaomei Yan, Jinglin Zhang, Lijun Tang. Synthesis of a Turn-On Fluorescent Probe for Hydrogen Sulfide and Its Application in Red Wine and Living Cells [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 308-312.
[12]	Siyi Zhou, Xu Ding, Yongmei Zhao, Jinghua Li, Wen Luo. A Flavone-Based Long-Wavelength Fluorescent Probe to Detect Biothiols in vitro and in vivo [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 178-185.
[13]	Binghan Lin, Jibin Zhuo, Caixia Lin, Yong Gao, Yaofeng Yuan. Synthesis and Nucleotide Recognition Properties of Carborane-Based Benzoimidazolium Cyclophane [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2551-2558.
[14]	Wei Ding, Bowen Cheng, Meng Wang, Qingyu Dou, Siying Li, Peng Zhang, Qianfu Luo. Advances in Aggregation-Induced Emission Molecules Based on Organic Photochromism [J]. Chinese Journal of Organic Chemistry, 2022, 42(2): 363-383.
[15]	Jiamin Tan, Yajun Yu, Meng Guan, Yunhui Zhao, Zilong Tang, Zhihua Zhou, Tao Guo. Design and Synthesis of Novel Aggregation-Induced Luminescence Molecules Based on Isoquinoline [J]. Chinese Journal of Organic Chemistry, 2022, 42(11): 3776-3783.

含肉桂酸酯基螺噁嗪的合成及性质研究

Synthesis and Properties of a Novel Spirooxazine Dye

PDF

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments