Investigation on Synthesis and Photostabilities of Novel Asymmetric Benzothiazole Trimethine Cyanine Dyes

doi:10.6023/cjoc1201091

Chin. J. Org. Chem. ›› 2012, Vol. 32 ›› Issue (08): 1445-1449.DOI: 10.6023/cjoc1201091 Previous Articles Next Articles

Articles

新型不对称苯并噻唑三次甲基菁染料的合成及光稳定性研究

陈秀英, 郭琳, 郑昌戈, 高海燕, 王海军, 张丹

江南大学食品胶体与生物技术教育部重点实验室江南大学化学与材料工程学院无锡 214122

收稿日期:2012-01-09 修回日期:2012-04-23 发布日期:2012-05-11
通讯作者: 陈秀英 E-mail:chenxiuying1975@163.com
基金资助:
国家自然科学基金(No.20706026)、中央高校基本科研业务费专项资金(Nos. JUSRP211A12, JUSRP21110)资助项目.

Investigation on Synthesis and Photostabilities of Novel Asymmetric Benzothiazole Trimethine Cyanine Dyes

Chen Xiuying, Guo Lin, Zheng Changge, Gao Haiyan, Wang Haijun, Zhang Dan

Key Laboratory of Food Colloids and Biotechnology, Ministry of Education, School of Chemical and Material Engineering, Jiangnan University, Wuxi 214122

Received:2012-01-09 Revised:2012-04-23 Published:2012-05-11
Supported by:
Project supported by the National Natural Science Foundation of China (No. 20706026) and the Fundamental Research Funds for the Central Universities (Nos. JUSRP211A12, JUSRP21110).

Novel asymmetric trimethine benzothiazole cyanine dyes with different N-substituents were synthesized and characterized by MS and ¹H NMR techniques. The maximums of absorption and emission spectra of the dyes in ethanol were in the range of 628～631 and 662～666 nm, respectively. The dyes were almost non-fluorescent in solvents, which can reduce the background interference greatly. The photodegradation experiment showed that the octyl group on quinoline ring and benzyl group on benzothiazole ring improved the photostabilites of the dyes obviously. The rate constants of photoreaction of the dyes 8a～8d were 6.38×10^-4, 12.5×10^-4, 2.68×10^-4 and 6.30×10^-4 mol·min^-1, respectively. Oxidation potentials were determined by cyclic voltammetry.

Key words: benzothiazole cyanine dye, photodegradation, cyclic voltammetry curves, fluorescence, oxidizing potential, photostability

Cite this article

Chen Xiuying, Guo Lin, Zheng Changge, Gao Haiyan, Wang Haijun, Zhang Dan . Investigation on Synthesis and Photostabilities of Novel Asymmetric Benzothiazole Trimethine Cyanine Dyes[J]. Chin. J. Org. Chem., 2012, 32(08): 1445-1449.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Williams, C. H. G. Trans. R. Soc. Edinburgh 1856, 21, 377.

[2] Chen, C.; Qi, X.; Zhou, B. J. Photochem. Photobiol., A: Chem. 1997, 109, 155.

[3] Beck, W. F.; Sauer, K. J. Phys. Chem. 1992, 96, 4658.

[4] Kietzmann, R.; Willig, F.; Weller, H.; Vogel, R.; Nath, D. N.;Eichberger, R.; Liska, P.; Lehnert, J. Mol. Cryst. Liq. Cryst. 1991, 194, 169.

[5] Kietzmann, R.; Ehret, A.; Spitler, M.; Willig, F. J. Am. Chem. Soc. 1993, 115, 1930.

[6] Mitsuo, K.; Satoshi, A. Chem. Commun. 2004, 988.

[7] Guo, M.; Xu, Y.; Shi, L.; Liang, C.; Wang, L.; Gao, Y.; Sun, S.; Cai, S. J. Photochem. Photobiol. A: Chem. 2005, 171, 231.

[8] Lanzafame, J. M.; Muenter, A. A.; Brumbaugh, D. V. Chem. Phys. 1996, 210, 79.

[9] Lanzafame, J. M.; Min, L.; Miller, R. J. D.; Muenter, A. A.; Parkinson, B. A. Mol. Cryst. Liq. Cryst. 1991, 194, 287.

[10] Zhou, X.; Zhou, J. Anal. Chem. 2004,76, 5302.

[11] Schuler, B.; Pannell, L. K. Bioconjugate Chem. 2002, 13, 1039.

[12] Vasu, N.; Curt, S. C. J. Org. Chem. 1981, 46, 4759.

[13] Lee, L. G.; Chen, C. H.; Chiu, L. A. Cytometry 1986, 7, 508.

[14] Benson, S. C.; Mathies, R. A.; Glazer, A. N. Nucleic Acids Res. 1993, 21, 5720.

[15] Lubitz, I.; Zikich, D.; Kotlyar, A. Biochemistry. 2010, 49, 3567.

[16] Bethge, L.; Singh, I.; Seitz, O. Org. Biomol. Chem. 2010, 8, 2439.

[17] Deligeorgiev, T.; Gadjev, N.; Vasilev, A.; Drexhage, K.-H.; Yarmoluk, S. M. Dyes Pigm. 2007, 72, 28.

[18] Chen, X.; Peng, X.; Cui, A.; Wang, B.; Wang, L.; Zhang, R. J. Photochem. Photobiol., A: Chem. 2006, 181, 79.

[19] Mizukami, T.; Ishiyama, M.; Sakata, T. US 6004816, 1999 [Chem. Abstr. 1998, 160, 78447].

[20] Karstens, T.; Kobs, K. J. Phys. Chem. 1980, 84, 1871.

[21] Velapoldi, R. A.; T?nnesen, H. H. J. Fluoresc. 2004, 14, 465.

[22] Petersen, M.; Hamed, A. A.; Pedersen, E. B.; Jacobsen, J. P. Bioconjugate Chem. 1999, 10, 66.

[23] St?rk, D.; Hamed, A. A.; Pedersen, E. B.; Jacobsen, J. P. Bioconjugate Chem. 1997, 8, 869.

[24] Timcheva, I.; Maximova, V.; Deligeorgiev, T.; Gadjev, N.; Sabnis, R.; Ivanov, I. FEBS Lett. 1997, 405, 141.

[25] Netzel, T. L.; Nafisi, K.; Zhao, M.; Lenhard, J. R.; Johnson, I. J. Phys. Chem. A 1995, 99, 17936.

[26] Jacobsen, J. P.; Pedersen, J. B.; Hansen, L. F.; Wemmer, D. E. Nucleic Acids Res. 1995, 23, 753-760.

[27] Chen, G. Fluorometry, 2nd ed., Science Press, Beijing, 1990, pp. 10～15 (in Chinese).(陈国珍, 荧光分析法, 第二版, 科学出版社, 北京, 1990, pp. 10～15.)

[28] Song, F.; Peng, X.; Lu, E.; Zhang, R.; Chen, X.; Song, B. J. Photochem. Photobiol., A: Chem. 2004, 168, 53.

[29] Chen, P.; Sun, S.; Hu, Y.; Qian, Z.; Zheng, D. Dyes Pigm. 1999, 41, 227.

[30] Rettig, W.; Strehmel, B.; Schrader, S.; Seifert, H. Applied Fluorescence in Chemistry, Biology and Medicine, Springer, London, 1998, pp. 193～240.

[31] Lenhard, J. R.; Cameron, A. D. J. Phys. Chem. 1993, 97, 4916.

[32] Kanofsky, J. R.; Sima, P. D. Photochem. Photobiol. 2000, 71, 361.

新型不对称苯并噻唑三次甲基菁染料的合成及光稳定性研究

Investigation on Synthesis and Photostabilities of Novel Asymmetric Benzothiazole Trimethine Cyanine Dyes

PDF

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[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]	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.
[3]	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.
[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]	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.
[15]	Xiaolong Zhao, Yuqing Li, Liangwu Guo, Qiyuan Ran, Huihui Wu, Zhen Zhang, Yingpeng Su, Pengxin Zhou, Na Yan. A Highly Selective and High-Contrast Colorimetric “Off-On” Chemosensor for Cu^2＋ Based on Boron-Dipyrromethene (BODIPY) Derivatives [J]. Chinese Journal of Organic Chemistry, 2022, 42(11): 3757-3765.