Synthesis of Anthraquinone-Based Thiacalixarene via Click Chemis-try and Its Fluorescence Sensing Towards Al3＋

Chin. J. Org. Chem. ›› 2011, Vol. 31 ›› Issue (12): 2121-2125. Previous Articles Next Articles

Full Papers

含蒽醌基硫桥杯芳烃的点击合成及其对铝离子的荧光传感

赵邦屯*^,1，曹世娜²，郭海明²，渠桂荣²

(¹洛阳师范学院化学系洛阳 471022)
(²河南师范大学化学与环境科学学院新乡 453007)

收稿日期:2011-07-04 修回日期:2011-09-16 发布日期:2011-09-23
通讯作者: 曹世娜 E-mail:csn407452454@yahoo.com.cn

Synthesis of Anthraquinone-Based Thiacalixarene via Click Chemis-try and Its Fluorescence Sensing Towards Al^3＋

Zhao Bangtun*^,1 Cao Shina² Guo Haim-ing² Qu Guirong²

(¹Department of Chemistry, Luoyang Normal University, Luoyang 471022)
(²College of Chemistry and Environmental Science, Henan Normal Univer-sity, Xinxiang 453007)

Received:2011-07-04 Revised:2011-09-16 Published:2011-09-23

Tetrabromobutoxy thiacalix[4]arene (1) was reacted with sodium azide (NaN₃) in dimentylformamide (DMF) to obtain tetraazidobutoxy thiacalix[4]arene (2). The sequent reaction of 2 with 1,8-bis(prop-2- ynyloxy)anthraquinone (3) catalyzed by CuSO₄/VcNa to gave a novel anthraquinone-based thiacalixarene compound 4, which was characterized by ¹H NMR, FT-IR, MS (MALDI-TOF) and elemental analysis. The fluorescence experiments have shown that compound 4 has a good selectivity with Al^3＋ and the complexation of 4 with Al^3＋ in a 1∶2 complex mode gives an enhanced fluorescence change at 559 nm. In CHCl₃-CH₃CN (V∶V＝3∶1) solvent, the binding constant for the complex 4 and Al^3＋ is 2670 dm³•mol^－1 at room temperature. Hence, compound 4 can be used as a new fluorescent sensor for the Al^3＋ ion.

Key words: thiacalix[4]arene, anthraquinone, Al^3＋ ion, fluorescent sensor

Cite this article

ZHAO Bang-Tun, CAO Shi-Na, GUO Hai-Ming, QU Gui-Rong. Synthesis of Anthraquinone-Based Thiacalixarene via Click Chemis-try and Its Fluorescence Sensing Towards Al^3＋[J]. Chin. J. Org. Chem., 2011, 31(12): 2121-2125.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

[1]	Lixin Ju, Qi Shao, Linchuan Lu, Hongfei Lu. A New Turn-On Fluorescent Chemosensor for Selective Detection of Al³⁺ Based on a Purine Schiff Base and Its Cell Imaging [J]. Chinese Journal of Organic Chemistry, 2022, 42(6): 1706-1712.
[2]	Lu Xue, Lihua Zhang, Chengyu Zhang, Xin Zhao, Weifan Dang, Zhaoxin Wang, Chunhua Wang, Tongchuan Suo, Xiaohui Yan. Discovery of Tiancimycin Congeners from Streptomyces sp. CB03234-S [J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 1241-1247.
[3]	Yinghao Liu, Fangxia Lin, Yinfeng Tan, Jingyu Yang, Bin Zhang, Xueming Zhou, Xinming Song. Three New Phenanthraquinones from the Root of Dendrobium nobile [J]. Chinese Journal of Organic Chemistry, 2021, 41(5): 2112-2115.
[4]	Zhang Jidong, Zhan Yan, Li-Hu Yuewen, Qi Yi, Wang Ruipeng, Meng Li. Recent Progress in Fluorescent Chemosensors for Selenium Compounds [J]. Chinese Journal of Organic Chemistry, 2020, 40(7): 1847-1859.
[5]	Ma Xuelin, Han Limin, Zhang Xiaoyong, Zhang Yuheng, Wang Li, Yang Kun, Ji Jie. Triazine Derivative for Fluorescence Sensing of Zr⁴⁺, Fe³⁺ Ions and Acetone [J]. Chinese Journal of Organic Chemistry, 2020, 40(6): 1745-1751.
[6]	Chang Yongxin, Li Bai, Guo Miao, Cai Yonghong, Xu Kuoxi. A Novel Logic Gate Fluorescent Sensor for the Sequential Detection of Cd²⁺ and Pyrophosphate Anion and Application in Cell Imaging [J]. Chin. J. Org. Chem., 2019, 39(9): 2485-2491.
[7]	Zhou Jianping, Wu Baogeng, Zhou Zhikuan, Tian Jiangwei, Yuan Aihua. A Novel Naphthalene-Fused Boron Dipyrromethene (BODIPY)-Based Near Infrared Fluorescent Probe for Detecting Fluoride in Living Cells [J]. Chin. J. Org. Chem., 2019, 39(2): 406-411.
[8]	Zhu Yangmin, Wang Zhonglong, Yang Jian, Xu Xu, Wang Shifa, Cai Zhengchun, Xu Haijun. N,N-Bis(2-pyridylmethyl)amine-Based Truxene Derivative as a Highly Sensitive Fluorescence Sensor for Cu²⁺ and Ni²⁺ Ion [J]. Chin. J. Org. Chem., 2019, 39(2): 427-433.
[9]	Hou Jiting, Li Kun, Qin Caiqin, Yu Xiaoqi. Review of the Small Molecular Fluorescent Sensors for Intracellular Reactive Oxygen Species [J]. Chin. J. Org. Chem., 2018, 38(3): 612-628.
[10]	Liu Zhanxiong, Yuan Jing, Zhang Zhenfeng, Yan Deyue, Zhang Wanbin. Design, Synthesis and Antitumor Activity of 1-Monosubstituted 1H-Naphtho[2,3-d]imidazole-4,9-diones and 1H-Anthra[2,3-d]imidazole-4,11-diones [J]. Chin. J. Org. Chem., 2018, 38(12): 3302-3317.
[11]	Zhou Chan, Qiu Bo, Zeng Yi, Chen Jinping, Yu Tianjun, Li Yi. A Reaction-Based Chemsensor for Hydrogen Sulfide Detection with Fluorescence Enhancement [J]. Chin. J. Org. Chem., 2017, 37(1): 92-96.
[12]	Zhang Pingzhu, Wei Xiao, Liu Huan, Wang Qiwei, Ma Chen, Rong Ruixue, Li Xiaoliu. Synthesis and Cytotoxicity of Azasugar Modified Anthraquinone Derivatives [J]. Chin. J. Org. Chem., 2016, 36(8): 1921-1925.
[13]	Tan Zan, Du Huan, Lü Xinyang, Bao Xiaoping. Synthesis and Recognition Properties of Carbazole Sulfonamide-Based Anion Receptor Containing the Aminoanthraquinone Signalling Units [J]. Chin. J. Org. Chem., 2016, 36(6): 1389-1394.
[14]	Yang Taiqun, Dai Shan, Qin Cuifang, Huang Kehan, Chen Yuting, Pan Haifeng, Zhang Sanjun, Zhang Kun, Xu Jianhua. Selective Detection of Homocysteine by Using Poly Methyl Vinyl Ether-alt-Maleic Silver Clusters [J]. Chin. J. Org. Chem., 2016, 36(4): 867-871.
[15]	Zhang Chenglu, Guo Yang, Chen Ying, Sun Lijie, Cheng Anqi, Zhao Na, Zhao Baocheng, Tang Jie, Xi Huan. Synthesis and Properties of Novel Tripod Type Multi-benzimidazole Quaternary Ammonium Compounds [J]. Chin. J. Org. Chem., 2015, 35(8): 1665-1672.

含蒽醌基硫桥杯芳烃的点击合成及其对铝离子的荧光传感

Synthesis of Anthraquinone-Based Thiacalixarene via Click Chemis-try and Its Fluorescence Sensing Towards Al^3＋

PDF

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments