Synthesis of crescent aromatic oligoamides with preorganized chelating groups and their extraction towards transition metal ions

Journal of Hazardous Materials

Volumn 217-218, Issue , 2012, Pages 171-176

  Yang, Xinshi ^a   Chen, Long ^a   Yang, Yongan ^a   He, Youzhou ^a   Zou, Shuliang ^a   Feng, Wen ^a   Yang, Yuanyou ^a   Liu, Ning ^a   Liao, Jiali ^a   Yuan, Lihua ^a  

^a SICHUAN UNIVERSITY   (China)

Author keywords

Aromatic oligoamide; Hydrogen bonding; Solvent extraction; Transition metal ion

Indexed keywords

AROMATIC OLIGOAMIDES; CHELATING GROUPS; DIMERIC LIGANDS; EXTRACTABILITY; EXTRACTION CONSTANTS; INTRAMOLECULAR HYDROGEN BOND; LIQUID-LIQUID EXTRACTION; METAL CATION; OLIGOAMIDES; OXYGEN DONORS; UV-VIS SPECTROMETRY;

AROMATIC COMPOUNDS; AROMATIZATION; COBALT COMPOUNDS; COPPER; HYDROGEN BONDS; LEAD; LEAD COMPOUNDS; LIGANDS; MERCURY (METAL); METAL IONS; STOICHIOMETRY; TRANSITION METALS;

SOLVENT EXTRACTION;

5 ACETAMIDO N (5 (ETHYLCARBAMOYL) 2,4 BIS (2 ETHYLHEXYLOXY)PHENYL) 2,4 DIMETHOXYBENZ AMIDE; AROMATIC AMIDE; CADMIUM; CATION; COBALT; COPPER ION; LEAD; MERCURY; N1,N3 BIS (5 (5 (ETHYLCARBAMOYL) 2,4 BIS (2 ETHYLHEXYLOXY)PHENYLCARBAMOYL) 2,4 DIMETHOXY PHENYL) 4,6 BIS (2 ETHYLHEXYLOXY)ISOPHTHALAMIDE; N1,N3 BIS (5 (ETHYLCARBAMOYL) 2,4 DIMETHOXYPHENYL) 4,6 BIS (2 ETHYLHEXYLOXY)ISOPHTHAL AMIDE; NICKEL; PICRIC ACID; SILVER; UNCLASSIFIED DRUG; ZINC ION;

AROMATIC HYDROCARBON; CATION; CHELATING AGENT; CHEMICAL BONDING; EXTRACTION METHOD; LIGAND; ORGANIC NITROGEN COMPOUND; OXYGEN; SOLVENT; STOICHIOMETRY; TRANSITION ELEMENT;

ARTICLE; HYDROGEN BOND; LIQUID LIQUID EXTRACTION; SPECTROMETRY; STOICHIOMETRY; SYNTHESIS; ULTRAVIOLET SPECTROSCOPY;

AMIDES; CATIONS; CHELATING AGENTS; MAGNETIC RESONANCE SPECTROSCOPY; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; TRANSITION ELEMENTS;

EID: 84859821452     PISSN: 03043894     EISSN: 18733336     Source Type: Journal    
DOI: 10.1016/j.jhazmat.2012.03.010     Document Type: Article

References (38)

1. Carraher C.E. Giant Molecules: Essential Materials for Everyday Living and Problem Solving 2003, Hoboken, New Jersey. second ed.
2. Saraogi I., Hamilton A.D. Recent advances in the development of aryl-based foldamers. Chem. Soc. Rev. 2009, 38:1726-1743.
3. Gong B. Hollow crescents, helices, and macrocycles from enforced folding and folding-assisted macrocyclization. Acc. Chem. Res. 2008, 41:1376-1386.
4. Hecht S., Huc I. Foldamers: Structure, Properties and Applications 2007, Weinheim, Wiley-VCH.
5. Li Z.T., Hou J.L., Li C. Peptide mimics by linear arylamides: a structural and functional diversity test. Acc. Chem. Res. 2008, 41:1343-1353.
6. Gong B. Crescent oligoamides: from acyclic macrocycles to folding nanotubes. Chem. Eur. J. 2001, 7:4336-4342.
7. Yuan L.H., Sanford A.R., Feng W., Zhang A.M., Zhu J., Zeng H.Q., Yamato K., Li M.F., Ferguson J.S., Gong B. Synthesis of crescent aromatic oligoamides. J. Org. Chem. 2005, 70:10660-10669.
8. Yuan L.H., Zeng H.Q., Yamato K., Sanford A.R., Feng W., Atreya H.S., Sukumaran D.K., Szyperski T., Gong B. Helical aromatic oligoamides: reliable, readily predictable folding from the combination of rigidified structural motifs. J. Am. Chem. Soc. 2004, 126:16528-16537.
9. Feng W., Yamato K., Yang L.Q., Ferguson J.S., Zhong L.J., Zou S.L., Yuan L.H., Zeng X.C., Gong B. Efficient kinetic macrocyclization. J. Am. Chem. Soc. 2009, 131:2629-2637.
10. Yang L.Q., Zhong L.J., Yamato K., Zhang X.H., Feng W., Deng P.C., Yuan L.H., Zeng X.C., Gong B. Aromatic oligoamide macrocycles from the bimolecular coupling of folded oligomeric precursors. New J. Chem. 2009, 33:729-733.
11. Zou S.L., He Y.Z., Yang Y.A., Zhao Y., Yuan L.H., Feng W., Yamato K., Gong B. Improving the efficiency of forming 'unfavorable' products: eight-residue macrocycles from folded aromatic oligoamide precursors. Synlett 2009, 9:1437-1440.
12. Yang Y.A., Feng W., Hu J.C., Zou S.L., Gao R.Z., Yamato K., Kline M., Cai Z.H., Gao Y., Wang Y.B., Li Y.B., Yang Y.L., Yuan L.H., Zeng X.C., Gong B. Strong aggregation and directional assembly of aromatic oligoamide macrocycles. J. Am. Chem. Soc. 2011, 133:18590-18593.
13. Zhong L.J., Chen L., Feng W., Zou S.L., Yang Y.Y., Liu N., Yuan L.H. Shape-persistent macrocycles: efficient extraction towards lanthanide and actinide elements. J. Incl. Phenom. Macrocycl. Chem. 2012, 72:367-373.
14. Hayashita T., Sawano H., Higuchi T., Indo M., Hiratani K., Zhang Z.Y., Bartsch R.A. Molecular design of acyclic polyether dicarboxylic acids possessing pseudo-18-crown-6 frameworks for selective lead(II) extraction. Anal. Chem. 1999, 71:791-795.
15. Kim J.S., Cho M.H., Cho J.H., Lee J.H., Bartsch R.A., Lee Y.I., Kim I.H. Metal ion complexation by acyclic polyethers with lipophilic amide, thioamide, and amine end groups. Talanta 2000, 51:99-105.
16. Gokel G.W., Leevy W.M., Weber M.E. Crown ethers: sensors for ions and molecular scaffolds for materials and biological models. Chem. Rev. 2004, 104:2723-2750.
17. Tsukanov A.V., Dubonosov A.D., Bren V.A., Minkin V.I. Organic chemosensors with crown-ether groups (review). Chem. Heterocycl. Compd. 2008, 44:899-923.
18. Förstner U., William G.T.W. Metal Pollution in the Aquatic Environment 1983, Springer-Verlag, Berlin.
19. Uria J.E.S., Sanz-Medel A. Inorganic and methylmercury speciation in environmental samples. Talanta 1998, 47:509-524.
20. Say R., Birlik E., Erdemgil Z., Denizli A., Ersöz A. Removal of mercury species with dithiocarbamate-anchored polymer/organosmectite composites. J. Hazard. Mater. 2008, 150:560-564.
21. Zolfaghari G., Esmaili-Sari A., Anbia M., Younesi H., Amirmahmoodi S., Ghafari-Nazari A. Taguchi optimization approach for Pb(II) and Hg(II) removal from aqueous solutions using modified mesoporous carbon. J. Hazard. Mater. 2011, 192:1046-1055.
22. Li S.X., Zheng F.Y., Huang Y., Ni J.C. Thorough removal of inorganic and organic mercury from aqueous solutions by adsorption on Lemna minor powder. J. Hazard. Mater. 2011, 186:423-429.
23. 2+ from water. J. Hazard. Mater. 2011, 189:450-457.
24. Idris S.A., Harvey S.R., Gibson L.T. Selective extraction of mercury(II) from water samples using mercapto functionalised-MCM-41 and regeneration of the sorbent using microwave digestion. J. Hazard. Mater. 2011, 193:171-176.
25. 2-macrocyclic crown ligands. J. Incl. Phenom. Macrocycl. Chem. 2008, 60:17-24.
26. López J.M., Borrajo J.L., García E.D.M., Arrans J.R., Estévez M.C.H., Castillo A.J.S. Multivariate analysis of contamination in the mining district of Linares (Jaén, Spain). Appl. Geochem. 2008, 23:2324-2336.
27. Reddy M.L.P., Francis T. Recent advances in the solvent extraction of mercury(II) with calixarenes and crown ethers. Solvent Extr. Ion Exch. 2001, 19:839-863.
28. Liu K., Shi W., Cheng P. The coordination chemistry of Zn(II), Cd(II) and Hg(II) complexes with 1,2,4-triazole derivatives. Dalton Trans. 2011, 40:8475-8490.
29. Grant G.J. Mercury(II) complexes with thiacrowns and related macrocyclic ligands. Struct. Bond. 2006, 120:107-141.
30. Nolan E.M., Lippard S.J. Tools and tactics for the optical detection of mercuric ion. Chem. Rev. 2008, 108:3443-3480.
31. Pedersen C. New macrocyclic polyethers. J. Am. Chem. Soc. 1970, 92:391-394.
32. Zhu J., Parra R.D., Zeng H.Q., Skrzypczak-Jankun E., Zeng X.C., Gong B. A new class of folding oligomers: crescent oligoamides. J. Am. Chem. Soc 2000, 122:4219-4220.
33. Alp H., ök H.Z.G., Kantekin H., Ocak ü. Synthesis and metal ion binding properties of thiaaza crown macrocycles. J. Hazard. Mater. 2008, 159:519-522.
34. Miessler G.L., Tarr D.A. Inorganic Chemistry 1998, Prentice-Hall, New Jersey.
35. Shi X.D., Mullaugh K.M., Fettinger J.C., Jiang Y., Hofstadler S.A., Davis J.T. Lipophilic G-quadruplexes are self-assembled ion pair receptors, and the bound anion modulates the kinetic stability of these complexes. J. Am. Chem. Soc. 2003, 125:10830-10841.
36. Ren C.L., Maurizot V., Zhao H.Q., Shen J., Zhou F., Ong W.Q., Du Z.Y., Zhang K., Su H.B., Zeng H.Q. Five-fold-symmetric macrocyclic aromatic pentamers: high-affinity cation recognition, ion-pair-induced columnar stacking, and nanofibrillation. J. Am. Chem. Soc. 2011, 133:13930-13933.
37. Park C., Chun S., Bartsch R.A. Effect of conformation on metal ion extraction by calix[4]arene dicarboxylic acids. J. Incl. Phenom. Macrocycl. Chem. 2010, 66:95-105.
38. 3-symmetric triphenoxymethane platform. Inorg. Chem. 2002, 41:1707-1716.