Synthesis of a crescent aromatic oligothioamide and its high selectivity in recognizing copper(Ⅱ) ions

注册 English

Synthesis of a crescent aromatic oligothioamide and its high selectivity in recognizing copper(Ⅱ) ions

Qian Jiang , Lu-Tao He , Shun-Zhong Luo , Yan-Qiu Yang , Liang Yang , Wen Feng , Li-Hua Yuan

Citation: Qian Jiang, Lu-Tao He, Shun-Zhong Luo, Yan-Qiu Yang, Liang Yang, Wen Feng, Li-Hua Yuan. Synthesis of a crescent aromatic oligothioamide and its high selectivity in recognizing copper(Ⅱ) ions[J]. Chinese Chemical Letters, 2013, 24(10): 881-884. shu

shu

Synthesis of a crescent aromatic oligothioamide and its high selectivity in recognizing copper(Ⅱ) ions

通讯作者: Wen Feng,

基金项目:
This work was supported by the National Natural Science Foundation (No. 21172158) (No. 21172158)

NSAF (No. 11076018) (No. 11076018)

Technology Support Programme (No. 2011FZ0048) (No. 2011FZ0048)

the National Fund of China for Fostering Talents in Basic Science (No. J1210004) (No. J1210004)

Technology of Ministry of Education (No. 2010-08). Analytical & Testing Center of Sichuan University is acknowledged for NMR analyses. (No. 2010-08)

摘要: Functionalization of shape-persistent aromatic oligoamides still represents a difficult task nowadays. A crescent aromatic oligothioamide was synthesized by simple thionation of the corresponding oligoamide with the Lawesson's reagent. The results from UV-vis spectra of the molecule upon metal ion complexation demonstrated its higher selectivity in recognizing Cu²⁺ ions compared to the oligoamide precursor. The stoichiometry of the complex formed between the thioamide and Cu²⁺ was found to be 1:1 with a binding constant of (4.3±0.9)×10⁴ mol/L.

关键词:

English

Synthesis of a crescent aromatic oligothioamide and its high selectivity in recognizing copper(Ⅱ) ions

1.
a Key Laboratory for Radiation Physics and Technology of Ministry of Education, College of Chemistry, Institute of Nuclear Science and Technology, Sichuan University, Chengdu 610064, China;
2.
b Institute of Nuclear Physics and Chemistry, CAEP, Mianyang 621900, China

Corresponding author: Wen Feng,

Received Date: 01 April 2013
Fund Project:

Abstract: Functionalization of shape-persistent aromatic oligoamides still represents a difficult task nowadays. A crescent aromatic oligothioamide was synthesized by simple thionation of the corresponding oligoamide with the Lawesson's reagent. The results from UV-vis spectra of the molecule upon metal ion complexation demonstrated its higher selectivity in recognizing Cu²⁺ ions compared to the oligoamide precursor. The stoichiometry of the complex formed between the thioamide and Cu²⁺ was found to be 1:1 with a binding constant of (4.3±0.9)×10⁴ mol/L.

Key words:

1. [1] B. Gong, Crescent oligoamide: from acyclic "macrocycles" to folding nanotubes, Chem. Eur. J. 7 (2001) 4336-4342.[1] B. Gong, Crescent oligoamide: from acyclic "macrocycles" to folding nanotubes, Chem. Eur. J. 7 (2001) 4336-4342.
2. [2] H. Jiang, C. Dolain, J.M. Léger, H. Gornitzka, I. Huc, Switching of chiral induction in helical aromatic oligoamides using solid state-solution state equilibrium, J. Am. Chem. Soc. 126 (2004) 1034-1035.[2] H. Jiang, C. Dolain, J.M. Léger, H. Gornitzka, I. Huc, Switching of chiral induction in helical aromatic oligoamides using solid state-solution state equilibrium, J. Am. Chem. Soc. 126 (2004) 1034-1035.
3. [3] Z.T. Li, J.L. Hou, C. Li, et al., Shape-persistent aromatic amide oligoamide: new tools for supramolecular chemistry, Chem. Asian J. 1 (2006) 766-778.[3] Z.T. Li, J.L. Hou, C. Li, et al., Shape-persistent aromatic amide oligoamide: new tools for supramolecular chemistry, Chem. Asian J. 1 (2006) 766-778.
4. [4] H.Y. Hu, W. Xue, Z.Q. Hu, et al., Probing the dynamic environment-associated conformational conversion from secondary to supersecondary structures in oligo(phenanthroline dicarboxamide)s, J. Org. Chem. 74 (2009) 4949-4957.[4] H.Y. Hu, W. Xue, Z.Q. Hu, et al., Probing the dynamic environment-associated conformational conversion from secondary to supersecondary structures in oligo(phenanthroline dicarboxamide)s, J. Org. Chem. 74 (2009) 4949-4957.
5. [5] W.Q. Ong, H.Q. Zhao, Z.Y. Du, et al., Computational prediction and experimental verification of pyridine-based helical oligoamides containing four repeating units per helical turn, Chem. Commun. 47 (2011) 6416-6418.[5] W.Q. Ong, H.Q. Zhao, Z.Y. Du, et al., Computational prediction and experimental verification of pyridine-based helical oligoamides containing four repeating units per helical turn, Chem. Commun. 47 (2011) 6416-6418.
6. [6] I. Saraogi, A.D. Hamilton, Recent advances in the development of aryl-based foldmers, Chem. Soc. Rev. 38 (2009) 1726-1743.[6] I. Saraogi, A.D. Hamilton, Recent advances in the development of aryl-based foldmers, Chem. Soc. Rev. 38 (2009) 1726-1743.
7. [7] J. Zhu, R.D. Parra, H.Q. Zeng, et al., A new class of folding oligomers: crescent oligoamides, J. Am. Chem. Soc. 122 (2000) 4219-4220.[7] J. Zhu, R.D. Parra, H.Q. Zeng, et al., A new class of folding oligomers: crescent oligoamides, J. Am. Chem. Soc. 122 (2000) 4219-4220.
8. [8] L.H. Yuan, W. Feng, K. Yamato, et al., Highly efficient, one-step macrocyclizations assisted by the folding and preorganization of precursor oligomers, J. Am. Chem. Soc. 126 (2004) 11120-11121.[8] L.H. Yuan, W. Feng, K. Yamato, et al., Highly efficient, one-step macrocyclizations assisted by the folding and preorganization of precursor oligomers, J. Am. Chem. Soc. 126 (2004) 11120-11121.
9. [9] W. Feng, K. Yamato, L.Q. Yang, et al., Efficient kinetic macrocyclization, J. Am. Chem. Soc. 131 (2009) 2629-2637.[9] W. Feng, K. Yamato, L.Q. Yang, et al., Efficient kinetic macrocyclization, J. Am. Chem. Soc. 131 (2009) 2629-2637.
10. [10] Y.A. Yang, W. Feng, J.C. Hu, et al., Strong aggregation and directional assembly of aromatic oligoamide macrocycles, J. Am. Chem. Soc. 133 (2011) 18590-18593.[10] Y.A. Yang, W. Feng, J.C. Hu, et al., Strong aggregation and directional assembly of aromatic oligoamide macrocycles, J. Am. Chem. Soc. 133 (2011) 18590-18593.
11. [11] H.L. Fu, Y. Liu, H.Q. Zeng, Shape-persistent H-bonded macrocyclic aromatic pentamers, Chem. Commun. 49 (2013) 4127-4144.[11] H.L. Fu, Y. Liu, H.Q. Zeng, Shape-persistent H-bonded macrocyclic aromatic pentamers, Chem. Commun. 49 (2013) 4127-4144.
12. [12] W.Q. Ong, H.Q. Zeng, Rapid construction of shape-persistent H-bonded macrocycles via one-pot H-bonding-assisted macrocyclization, J. Incl. Phenom. Macrocycl. Chem. (2013), http://dx.doi.org/10.1007/s10847-012-0243-4.[12] W.Q. Ong, H.Q. Zeng, Rapid construction of shape-persistent H-bonded macrocycles via one-pot H-bonding-assisted macrocyclization, J. Incl. Phenom. Macrocycl. Chem. (2013), http://dx.doi.org/10.1007/s10847-012-0243-4.
13. [13] X.S. Yang, L. Chen, Y.A. Yang, et al., Synthesis of crescent aromatic oligoamides with preorganized chelating groups and their extraction towards transition metal ion, J. Hazard. Mater. 217-218 (2012) 171-176.[13] X.S. Yang, L. Chen, Y.A. Yang, et al., Synthesis of crescent aromatic oligoamides with preorganized chelating groups and their extraction towards transition metal ion, J. Hazard. Mater. 217-218 (2012) 171-176.
14. [14] S.L. Zou, L.T. He, J. Zhang, et al., Tunable mesogens based on shape-persistent aromatic oligoamides: from lamellar, columnar, to nematic liquid crystalline phase, Org. Lett. 14 (2012) 3584-3587.[14] S.L. Zou, L.T. He, J. Zhang, et al., Tunable mesogens based on shape-persistent aromatic oligoamides: from lamellar, columnar, to nematic liquid crystalline phase, Org. Lett. 14 (2012) 3584-3587.
15. [15] D.M. Roundhill, J.Y. Shen, Phase transfer extraction of heavy metals, in: Z. Asfari, V. Bohmer, J. Harrowfield, J. Vicens (Eds.), Calixarenes, Kluwer Academic Publishers, Dordrecht, 2001, pp. 407-420.[15] D.M. Roundhill, J.Y. Shen, Phase transfer extraction of heavy metals, in: Z. Asfari, V. Bohmer, J. Harrowfield, J. Vicens (Eds.), Calixarenes, Kluwer Academic Publishers, Dordrecht, 2001, pp. 407-420.
16. [16] P. Wang, T. Okamura, H.P. Zhou, et al., Metal complex with terpyrindine derivative ligand as highly selective colorimetric sensor for iron(Ⅲ), Chin. Chem. Lett. 24 (2013) 20-22.[16] P. Wang, T. Okamura, H.P. Zhou, et al., Metal complex with terpyrindine derivative ligand as highly selective colorimetric sensor for iron(Ⅲ), Chin. Chem. Lett. 24 (2013) 20-22.
17. [17] M.C. Zhang, Q. Zhou, Y. Zhou, et al., Efficient absorption and desorption of Cu²⁺ by a novel acid-resistant magnetic weak acid resin, Chin. Chem. Lett. 23 (2012) 1267-1270.[17] M.C. Zhang, Q. Zhou, Y. Zhou, et al., Efficient absorption and desorption of Cu²⁺ by a novel acid-resistant magnetic weak acid resin, Chin. Chem. Lett. 23 (2012) 1267-1270.
18. [18] N. Shao, Y. Zhang, S.M. Cheung, et al., Copper ion-selective fluorescent sensor based on the inner filter effect using a spiropyran derivative, Anal. Chem. 77 (2005) 7294-7303.[18] N. Shao, Y. Zhang, S.M. Cheung, et al., Copper ion-selective fluorescent sensor based on the inner filter effect using a spiropyran derivative, Anal. Chem. 77 (2005) 7294-7303.
19. [19] Y. Zhou, F. Wang, Y. Kim, et al., Yoon, Cu²⁺-selective ratiometric and "off-on" sensor based on the rhodamine derivative bearing pyrene group, Org. Lett. 11 (2009) 4442-4445.[19] Y. Zhou, F. Wang, Y. Kim, et al., Yoon, Cu²⁺-selective ratiometric and "off-on" sensor based on the rhodamine derivative bearing pyrene group, Org. Lett. 11 (2009) 4442-4445.
20. [20] M.J. Schwing-Weill, F. Arnaud, M.A. Mckervey, Modulation of the cation complexing properties in the lower rim chemically modified calixarene series, J. Phys. Org. Chem. 5 (1992) 496-501.[20] M.J. Schwing-Weill, F. Arnaud, M.A. Mckervey, Modulation of the cation complexing properties in the lower rim chemically modified calixarene series, J. Phys. Org. Chem. 5 (1992) 496-501.
21. [21] M. Zhu, M.J. Yuan, X.F. Liu, et al., Visible near-infrared chemosensor for mercury ion, Org. Lett. 10 (2008) 1481-1484.[21] M. Zhu, M.J. Yuan, X.F. Liu, et al., Visible near-infrared chemosensor for mercury ion, Org. Lett. 10 (2008) 1481-1484.

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