title: Synthesis and luminescence properties of iridium(III) azide- and triazole-bisterpyridine complexes.
abstract: We describe here the synthesis of azide-functionalised iridium(III) bisterpyridines using the "chemistry on the complex" strategy. The resulting azide-complexes are then used in the copper(I)-catalysed azide-alkyne Huisgen 1,3-dipolar cycloaddition "click chemistry" reaction to from the corresponding triazole-functionalised iridium(III) bisterpyridines. The photophysical characteristics, including lifetimes, of these compounds were also investigated. Interestingly, oxygen appears to have very little effect on the lifetime of these complexes in aqueous solutions. Unexpectedly, sodium ascorbate acid appears to quench the luminescence of triazole-functionalised iridium(III) bisterpyridines, but this effect can be reversed by the addition of copper(II) sulfate, which is known to oxidize ascorbate under aerobic conditions. The results demonstrate that iridium(III) bisterpyridines can be functionalized for use in "click chemistry" facilitating the use of these photophysically interesting complexes in the modification of polymers or surfaces, to highlight just two possible applications.
authors.affiliation: School of Chemistry, the University of New South Wales, NSW 2052, Australia.
authors.forename: Daniel C
authors.initials: DC
authors.lastname: Goldstein
authors.forename: Joshua R
authors.initials: JR
authors.lastname: Peterson
authors.forename: Yuen Yap
authors.initials: YY
authors.lastname: Cheng
authors.forename: Raphael G C
authors.initials: RG
authors.lastname: Clady
authors.forename: Timothy W
authors.initials: TW
authors.lastname: Schmidt
authors.forename: Pall
authors.initials: P
authors.lastname: Thordarson
mesh_terms: D001386:Azides / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D057930:Click Chemistry; D003300:Copper / Q000737:chemistry; D007495:Iridium / Q000737:chemistry*; D049449:Luminescence; D015394:Molecular Structure; D011108:Polymers / Q000737:chemistry; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D001386:Azides; D011108:Polymers; D014230:Triazoles; D007495:Iridium; D003300:Copper
references.citation: Angew Chem Int Ed Engl. 2001 Jun 1;40(11):2004-2021
references.pmid: 11433435
references.citation: Inorg Chem. 2004 May 17;43(10):3057-66
references.pmid: 15132611
references.citation: Bioconjug Chem. 2009 Jun;20(6):1129-38
references.pmid: 19453101
references.citation: Chem Soc Rev. 2011 May;40(5):2508-24
references.pmid: 21253643
references.citation: Appl Microbiol Biotechnol. 2006 Nov;73(2):243-54
references.pmid: 17061132
references.citation: Org Biomol Chem. 2013 Jul 28;11(28):4602-12
references.pmid: 23715338
references.citation: Angew Chem Int Ed Engl. 2002 Jul 15;41(14):2596-9
references.pmid: 12203546
references.citation: Dalton Trans. 2009 Feb 28;(8):1267-82
references.pmid: 19462644
references.citation: Anal Biochem. 1986 Jul;156(1):239-43
references.pmid: 3740413
references.citation: Dalton Trans. 2011 Mar 7;40(9):2053-61
references.pmid: 21218240
references.citation: Chem Commun (Camb). 2005 Sep 7;(33):4172-4
references.pmid: 16100593
references.citation: Dalton Trans. 2008 Apr 28;(16):2081-99
references.pmid: 18398532
references.citation: Chem Rev. 2008 Jun;108(6):1834-95
references.pmid: 18543874
references.citation: Org Biomol Chem. 2010 Jan 7;8(1):151-62
references.pmid: 20024146
references.citation: Acc Chem Res. 2008 Jul;41(7):857-71
references.pmid: 18543956
references.citation: Chem Soc Rev. 2010 Feb;39(2):638-55
references.pmid: 20111785
references.citation: Chem Commun (Camb). 2007 May 21;(19):1899-901
references.pmid: 17695222