Preparation of Polymeric Metal Complex Containing Azo Dye Rotaxane

Won Young Kang; Jong Seung Park (박종승)

Preparation of Polymeric Metal Complex Containing Azo Dye Rotaxane

Textile Coloration and Finishing
Abbr : Text. Color. and Finish.
2011, 23(3), pp.163-168
Publisher : The Korean Society Of Dyers And Finishers
Research Area : Engineering > Fiber Engineering > Dyeing Engineering

Won Young Kang ¹, Jong Seung Park ¹

¹동아대학교

Accredited

ABSTRACT

In this article, we synthesized an azo dye rotaxane containing bis(8-hydroxyquinoline) group and its polymeric metal complex with zinc. The azo dye rotaxane exhibits high pH sensitivity, solvatochromism and zinc (II) ion sensings in aqueous solution. These behaviors came from the tautomeric equilibrium between azo-hydrazone tautomers and the formation of extended conjugation. The structure of polymeric zinc complexed dye rotaxane was confirmed with NMR and FT-IR measurements. The existence of CD rings, provided by dye rotaxane formation, was found to be very beneficial in improving aqueous solubility of polymeric metal complex.

KEYWORDS

cyclodextrin, azo dye, dye rotaxane, pseudorotaxane, polymeric metal complex, 8-hydroxyquinoline

Citation status

* References for papers published after 2023 are currently being built.

[book] R. G. W. Hollingshead / 1954 / Oxine and its Derivatives Vols.I-IV / Butterworths

[journal] S. Wang / 2001 / Luminescence and Electroluminescence of Al(III), B(III), Be(II) and Zn(II) Complexes with Nitrogen Donors / Coord. Chem. Rev 215(1) : 79~98

[journal] T. J. Hurley / 1964 / Alkyl- and Arylaluminum Complexes I, The Reaction of Trialkyl- and Triarylaluminum with Bidendate Ligands / Inorg. Chem 3(5) : 692~696

[journal] C. W. Tang / 1987 / Organic Electroluminescent Diodes / Appl. Phys. Lett 51(12) : 913~915

[journal] C. H. Chen / 1998 / Metal Chelates as Emitting Materials for Organic Electroluminescence / Coord. Chem. Rev 171(1) : 161~174

[journal] M. Ghedini / 2003 / Synthesis and Photophysical Characterization of Soluble Photoluminescent Metal Complexes with Substituted 8-hydroxyquinolines / Synth. Met 138(1) : 189~192

[journal] M. Ceccato / 1997 / α-cyclodextrin/polyethylene Glycol Polyrotaxane: A Study of the Threading Process / Langmuir 13(9) : 2436~2439

[journal] A. Harada / 2001 / Cyclodextrin-based Molecular Machines / Acc. Chem. Res 34(6) : 456~464

[journal] S. Anderson / 1997 / Azo-dye Rotaxane / Angew. Chem. Int. Ed 36(12) : 1310~1313

[journal] M. R. Craig / 2001 / Rotaxane-encapsulation Enhances the Stability of an Azo Dye, in Solution and when Bonded to Cellulose / Angew. Chem. Int. Ed 40(6) : 1071~1074

[journal] M. Wei / 2002 / Manipulation of Nylon-6 Crystal Structures with its α-cyclodextrin Inclusion Complex / Macromolecules 35(21) : 8039~8044

[journal] N. Yamaguchi / 1998 / Dendritic Pseudorotaxanes / Angew. Chem. Int. Ed 37(23) : 3275~3279

[journal] A. Harada / 1994 / Doublestranded Inclusion Complexes of Cyclodextrin Threaded on Poly(ethylene glycol) / Nature 370(6485) : 126~128

[journal] P. N. Taylor / 2000 / Insulated Molecular Wires: Synthesis of Conjugated Polyrotaxanes by Suzuki Coupling in Water / Angew. Chem. Int. Ed 39(19) : 3456~3460

[journal] F. Cacialli / 2002 / Cyclodextrinthreaded Conjugated Polyrotaxanes as Insulated Wires with Reduced Interstrand Interactions / Nat. Mater 1(3) : 160~164

[journal] S. Anderson / 1996 / Synthesis of a Water-soluble Conjugated [3]rotaxane / Angew. Chem. Int. Ed 35(17) : 1956~1959

[journal] J. S. Fritz / 1957 / Complexometric Titrations using Azoxine Indicators / Anal. Chem 29(5) : 821~825

[journal] M. A. El-Gahami / 2003 / Synthetic and Spectroscopic Studies of Polymeric Metal Complexes Involving 1,4-[5-disulphonyl-8-hydroxyquinoline] piperazine / J. Inorg. Organomet. Polym 13(1) : 41~48

[journal] A. Z. El-Sonbati / 2002 / Stereochemistry of New Nitrogen Containing Heterocyclic Aldehyde IX, Spectroscopic Studies on Novel Mixed-ligand Complexes of Rh(III) / Spectrochim. Acta A 58(12) : 2771~2778

[journal] Y. Zhou / 2009 / Novel Polymeric Metal Complexes of 2,7-Bis[2-(2`-pyridyl)benzimidazole] -9,9`-dioctylfluorene with Cu(II) and Zn(II): Synthesis and Luminescence Properties / J. Inorg. Organomet. P 19(3) : 328~334

[journal] H. Huang / 2008 / Synthesis and Luminescence Properties of Polymeric Metal Complexes Containing bis(8-hydroxyquinoline) Goup / Eur. Polym. J 44(9) : 2944~2950

[journal] T. Zhao / 2003 / Direct Synthesis of Cyclodextrin-rotaxanated Poly(ethylene glycol)s and their Self-diffusion Behavior in Dilute Solution / Macromolecules 36(26) : 9859~9865

[journal] A. S. A. Zidan / 2000 / Mixed Ligand Complexes of 5-Arylazo-8-hydroxyqinoline and α-Amino Acids with Co(II), Ni(II) and Cu(II) / J. Therm. Anal. Cal 62(3) : 665~679

[journal] M. Ghdini / 2002 / Synthesis and Photophysical Characterization of Luminescent zinc Complexes with 5-Substituted-8-hydroxyquinolines / J. Chem. Soc. Dalton Trans 17 : 3406~3409

[journal] M. J. Jozwiakowski / 1985 / Aqueous Solubility Behavior of Three Cyclodextrins / Carbohyd. Res 143(9) : 51~59

[journal] T. Steiner / 1994 / Crystalline β -cyclodextrin Hydrate at Various Humidities: Fast, Continuous, and Reversible Dehydration Studied by X-ray Diffraction / J. Am Chem. Soc 116(12) : 5122~5128

KJCKorea
Journal Central

Textile Coloration and Finishing KCI Impact Factor : 0.0