128
Views
43
CrossRef citations to date
0
Altmetric
Original Articles

Synthesis of Polymeric Calix[4]arene Dinitrile and Diamino‐Derivatives: Exploration of Their Extraction Properties Towards Dichromate Anion

, , &
Pages 433-447 | Received 01 Jul 2003, Accepted 01 Oct 2003, Published online: 22 Aug 2007

References

  • Mueller , J. G. , Chapman , P. J. and Pritchard , P. H. 1989 . Creosote‐contaminated sites . J. Environ. Sci. Technol. , 23 : 1197 – 1201 .
  • Roundhill , D. M. 2001 . Extraction of Metals from Soils and Waters Dordrecht : Kluwer, Academic Publishers .
  • Holloway , J. M. , Dahlgren , R. A. , Hansen , B. and Casey , W. H. 1998 . Contribution of bedrock nitrogen to high nitrate concentrations in stream water . Nature , 395 : 785 – 788 . [CROSSREF]
  • Gutsche , C. D. 1998 . Calixarenes Revisited The Royal Society of Chemistry Cambridge .
  • Asfari , Z. , Böhmer , V. , Harrowfield , M. McB. and Vicens , J. 2001 . Calixarenes 2001 Dordrecht : Kluwer Academic Publishers .
  • Yilmaz , M. 1997 . Solution State Metal Complexes of Calixarenes and Polymeric Calixarenes Handbook of Engineering Polymeric Materials Edited by: Cheremisinoff , N. P. New York : Marcel Dekker Inc. .
  • Roundhill , D. M. 1995 . Metal complexes of calixarenes . Prog. Inorg. Chem. , 43 : 533 – 592 .
  • Roundhill , D. M. and Koch , H. F. 2002 . Methods and techniques for the selective extraction of recovery of oxoanions . Chem. Soc. Revs. , 31 : 60 – 67 . [CROSSREF]
  • Ikeda , A. and Shinkai , S. 1997 . Novel cavity design using calix[n]arenes skeletons: toward molecular recognition and metal binding . Chem. Rev. , 97 : 1713 – 1734 . [PUBMED] [INFOTRIEVE] [CROSSREF]
  • Yordanov , A. T. , Mague , J. T. and Roundhill , D. M. 1995 . Synthesis of heavy metal ion selective calix[4]arenes having sulfur containing lower‐rim functionalities . Inorg. Chem. , 34 : 5084 – 5087 .
  • Yordanov , A. T. and Roundhill , D. M. 1996 . Invited paper (New trends in calixarene chemistry special issue): chemically modified calix[4]arenes as selective complexants for heavy metal ions: comparison with crowns and thiacrowns . New J. Chem. , 20 : 447 – 451 .
  • Yordanov , A. T. , Whittlesey , B. R. and Roundhill , D. M. 1998 . Lower rim 2‐methylthioethoxy substituted calix[4]arenes as shape selective complexants for mercury and silver . Supramolecular Chem. , 9 : 13 – 15 .
  • Liu , Y. , Zhao , B.‐T. , Zhang , H.‐Y. , Ju , H.‐F. , Chen , L.‐X. and He , X.‐W. 2001 . Molecular design of calixarene, part 4, synthesis of novel double‐armed p‐(tert‐butyl)calix[4]arene‐derived amides and their lead(II) (Pb2+)‐selective‐electrode properties . Helv. Chim. Act. , 84 ( 7 ) : 1969 – 1975 . [CROSSREF]
  • Molard , Y. , Bureau , C. , Parrot‐Lopez , H. , Lamartine , R. and Regnouf‐de‐Vains , J.‐B. 1999 . Synthesis of calix[4]arene podands bearing two and four histidine or glycine groups at the lower rim. Complexation properties towards cobalt(II) chloride . Tetrahedron Lett. , 40 ( 35 ) : 6383 – 6387 . [CROSSREF]
  • Zhang , Y. , Yuan , H. , Huang , Z. , Zhou , J. , Kawanishi , Y. , Schatz , J. and Maas , G. 2001 . A p‐tert‐butylcalix[6]arene capped with a triethanolamine‐derived triple bridge . Tetrahedron , 57 ( 19 ) : 4161 – 4165 . [CROSSREF]
  • Reddy , M. L.P. and Françis , T. 2001 . Recent advances in the solvent extraction of mercury(II) with calixarenes and crown ethers . Solv. Extr. Ion Exch. , 19 ( 5 ) : 839 – 863 . [CROSSREF] [CSA]
  • Tuntulani , T. , Thavornyutikarn , P. , Poompradub , S. , Jaiboon , N. , Ruangpornvisuti , V. , Chaichit , N. , Asfari , Z. and Vicens , J. 2002 . Synthesis of tripodal aza crown ether calix[4]arenes and their supramolecular chemistry with transition, alkali metal ions and anions . Tetrahedron , 58 ( 52 ) : 10277 – 10285 . [CROSSREF]
  • Kavallieratos , K. and Moyer , B. A. 2001 . Attenuation of Hofmeister bias in ion‐pair extraction by a disulfonamide anion host used in strikingly effective synergistic combination with a calix‐crown Cs+ host . Chem. Commun. , : 1620 – 1621 . [CROSSREF]
  • Alpoguz , H. K. , Memon , S. , Ersöz , M. and Yilmaz , M. 2002 . Transport of Hg2+ through bulk liquid membrane using biscalix[4]arene nitrile derivetive as carrier: kinetic analysis . New J. Chem. , 26 : 477 – 480 . [CROSSREF]
  • Scheerder , J. , Engbersen , J. F.J. , Casnati , A. , Ungaro , R. and Reinhoudt , D. N. 1995 . J. Org. Chem. , 60 : 6448
  • Scheerder , J. , van Duynhoven , J. P.M. , Engbersen , J. F.J. and Reinhoudt , D. N. 1996 . Angew Chem., Int. Ed. Engl. , 35 : 1090 [CROSSREF]
  • Redman , J. E. , Beer , P. D. , Dent , S. W. and Drew , M. G.B. 1998 . Cooperative binding of potassium cation and chloride anion by novel rhenium(I) bipyridyl amide crown ether receptors . Chem. Commun. , : 231 – 232 . [CROSSREF]
  • Cooper , J. B. , Drew , M. G.B. and Beer , P. D. 2000 . Alkali metal cation cooperative anion recognition by heteroditopic bis(calix[4]arene) rhenium(I) bipyridyl and ferrocene receptor molecules . J. Chem. Soc., Dalton Trans. , : 2721 – 2728 . [CROSSREF]
  • Beer , P. D. and Cooper , J. B. 2000 . “ Calixarene based anion receptors ” . In Calixarenes in Action Edited by: Mandolini , L. and Ungaro , R. 111 – 143 . London : Imperial College Press .
  • Matthews , S. E. and Beer , P. D. 2001 . “ Calixarene‐based anion receptors ” . In Calixarenes 2001 Edited by: Asfari , Z. , Böhmer , V. , Harrowfield , J. and Vicens , J. 421 – 439 . Dordrecht : Kluwer Academic Publishers .
  • Gale , P. A. 2001 . Anion receptor chemistry: highlights from 1999 . Coord. Chem. Rev. , 213 : 79 – 128 . [CROSSREF]
  • Gale , P. A. 2003 . Anion and ion‐pair receptor chemistry: highlights from 2000 and 2001 . Coord. Chem. Rev. , 240 : 17 – 55 .
  • Tuntulani , T. , Poompradub , S. , Thavornyutikarn , P. , Jaiboon , N. , Ruangpornvisuti , V. , Chaichit , N. , Asfari , Z. and Vicens , J. 2001 . Aza crown ether calix[4]arenes containing cation and anion binding sites: Effects of metal ions towards anion binding ability . Tetrahedron Lett. , 42 : 5541 – 5544 . [CROSSREF]
  • Aeungmaitrepirom , W. , Hagege , A. , Asfari , Z. , Vicens , J. and Leroy , M. 2001 . Solvent extraction of selenate and chromate using a diaminocalix[4]arene . J. Incl. Phenom. and Macrocyclic Chem. , 40 ( 3 ) : 225 – 229 . [CROSSREF]
  • Falana , O. M. , Koch , H. F. , Roundhill , D. M. , Lumetta , C. J. and Hay , B. P. 1998 . Synthesis and extraction studies of 1,2‐ and 1,3‐disubstituted butylcalix[4]arene amides with oxyions; Geometric and conformational effects . J. Chem. Soc., Chem. Commun. , : 503 – 504 .
  • Georgiev , M. , Wolf , N. and Roundhill , D. M. 1997 . Lower rim alkylammonium substituted calix[4]arenes as “proton switchable” extractants for chromate and dichromate anions . Polyhedron , 16 ( 9 ) : 1581 – 1584 . [CROSSREF]
  • Wolf , N. J. , Georgiev , E. M. , Yordanov , A. T. , Whittlesey , B. R. , Koch , H. F. and Roundhill , D. M. 1999 . Synthesis and crystal structures of lower rim amine and carbamoyl substituted calixarenes as transfer agents for oxyanions between an aqueous and a chloroform phase . ibid. , 18 : 885 – 896 .
  • Yordanov , A. T. , Wolf , N. J. , Georgiev , E. M. , Koch , H. F. , Falana , O. M. and Roundhill , D. M. 1999 . Dervatized calix[4]arenes as selective phase transfer extractants for heavy metal andoxyion salts . Comments Inorg. Chem. , 20 ( 4–6 ) : 163 – 175 .
  • Memon , S. and Yilmaz , M. 2001 . A complimentary study of calixarene based bifunctional receptors for alkali or transition metal cations and Cr2O7 −2 anions . J. Mol. Struc. , 595 : 101 – 109 . [CROSSREF]
  • Yilmaz , A. , Memon , S. and Yilmaz , M. 2002 . Synthesis and study of allosteric effects on extraction behavior of novel calixarene‐based dichromate anion receptors . Tetrahedron , 58 : 7735 [CROSSREF]
  • Burrows , D. 1983 . Chromium: Metabolism and Toxicity Boca Raton, FL : CRC Press .
  • De Flora , S. and Wetterhahn , K. E. 1989 . [65]: Mechanisms of chromium metabolism and genotoxicity . Life Chem. Rep. , 7 : 169 – 244 .
  • Stearns , D. M. , Kennedy , L. J. , Courtney , K. D. , Giangrande , P. H. , Phieffer , L. S. and Wetterhahn , K. E. 1995 . Reduction of chromium(VI) by ascorbate leads to chromium‐DNA binding and DNA strand breaks in vitro . Biochemistry , 34 : 910 – 919 . [PUBMED] [INFOTRIEVE]
  • Wittbrodt , P. R. and Palmer , C. D. 1995 . Reduction of Cr(VI) in the presence of excessive soil fulvic acid . Environ. Sci. Technol. , 29 : 255 – 263 .
  • Deligöz , H. , Tavasli , M. and Yilmaz , M. 1994 . Selective extraction of Fe3+ by a polymeric calix[4]arene . J. Pol. Sci., Part A; Polym. Chem. , 32 ( 15 ) : 2961 – 2964 . [CROSSREF]
  • Yilmaz , A. , Memon , S. and Yilmaz , M. 1999 . Synthesis and binding properties of calix[4]arene telomers . J. Polym. Sci., Part A; Polym. Chem. , 37 ( 20 ) : 4351 – 4355 .
  • Memon , S. and Yilmaz , M. 2000 . Synthesis and complexation studies of 1,3‐dialkylated p‐tert‐butylcalix[4]arene telomers . Reactive Funct. Polym. , 44 ( 3 ) : 227 – 233 . [CROSSREF]
  • Memon , S. , Yilmaz , A. and Yilmaz , M. 2000 . Synthesis and comparative complexation studies of schiff base derivatives of p‐tert butylcalix[4]arene copolymers . J. Macromol. Sci. Part A, Pure and Appl. Chem. , 37 ( 8 ) : 865 – 879 . [CROSSREF]
  • Deligöz , H. and Yilmaz , M. 1996 . synthesis of polymer‐supported calix[4]arene and selective extraction of Fe3+ . Reactive Funct. Polym. , 31 ( 2 ) : 81 – 88 . [CROSSREF]
  • Memon , S. , Uysal , G. and Yilmaz , M. 2001 . Synthesis and complexation studies of p‐tert‐butylcalix[4]crown telomers . J. Macromol. Sci. Part A, Pure and Appl. Chem. , 38 ( 2 ) : 173 – 184 . [CROSSREF]
  • Memon , S. , Uysal , G. and Yilmaz , M. 2001 . Syntheses and binding properties of polymeric calix[4]crown‐4 . Reactive Funct. Polym. , 47 ( 3 ) : 165 – 174 . [CROSSREF]
  • Uysal , G. , Memon , S. and Yilmaz , M. 2001 . Synthesis and binding properties of polymeric calix[4]arene nitriles . Reactive Funct. Polym. , 50 ( 1 ) : 77 – 84 . [CROSSREF]
  • Dondoni , A. , Ghiglione , C. , Marra , A. and Scoponi , M. 1997 . Synthesis and receptor properties of calix[4]arene‐bisphenol‐a copolymers . Chem. Commun. , : 673 – 674 . [CROSSREF]
  • Dondoni , A. , Ghiglione , C. , Marra , A. and Scoponi , M. 1999 . Synthesis and characterization of bisphenol‐a copolyethers and copolyesters carrying calix[4]arene units in the main chains and their binding properties towards silver cations . Macromol. Chem. Phys. , 200 ( 1 ) : 77 – 86 . [CROSSREF]
  • Memon , S. , Oguz , O. , Yilmaz , A. , Tabakci , M. , Yilmaz , M. and Ertul , S. 2002 . Synthesis and extraction study of calix[4]arene dinitrile derivatives incorporated in a polymeric backbone with bisphenol‐A . J. Polymers and the Environment , 9 ( 2 ) : 97 – 101 . [CROSSREF]
  • Uysal , G. , Memon , S. and Yilmaz , M. 2002 . Synthesis of oligomeric calix[4]arene‐crowns as novel ionophores for alkali and transition metals . Polycyclic Aromatic Compounds , 22 ( 5 ) : 1075 – 1086 . [CROSSREF]
  • Gutsche , C. D. , Iqbal , M. and Stewart , D. 1986 . Calixarenes 18. Synthesis procedures for p‐tert‐butylcalix[4]arene . J. Org. Chem. , 51 : 742 – 745 .
  • Gutsche , C. D. and Lin , L.‐G. 1986 . Calixarenes 12: the synthesis of functionalized calixarenes . Tetrahedron , 42 ( 6 ) : 1633 – 1640 . [CROSSREF]
  • Collins , M. , McKervey , M. A. , Madigan , E. , Moran , M. B. , Owens , M. , Ferguson , G. and Harris , S. J. 1991 . Chemically modified calix[4]arenas. Regioselective synthesis of 1,3‐(distal)derivatives and related compounds. X‐ray crystal structure of a diphenoldinitrile . J. Chem. Soc. Perkin Trans. 1 , : 3137 – 3142 . [CROSSREF]
  • Memon , S. , Uysal , G. and Yilmaz , M. 2000 . Selective complexation of Hg2+ by bis‐calix[4]arene nitriles . Sep. Sci. and Tech. , 35 ( 8 ) : 1247 – 1256 . [CROSSREF] [CSA]
  • Perrin , D. D. 1965 . Dissociation Constants of Organic Bases in Aqueous Solution 15 London : Butterworths .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.