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  • 1.
    Hutchinson, Daniel J.
    et al.
    Department of Chemistry, University of Otago.
    Cameron, S. A.
    Department of Chemistry, University of Otago.
    Hanton, Lyall R.
    Department of Chemistry, University of Otago.
    Moratti, S. C.
    Department of Chemistry, University of Otago.
    Sensitivity of silver(I) complexes of a pyrimidine-hydrazone ligand to solvent, counteranion, and metal-to-ligand ratio changes2012In: Inorganic Chemistry, ISSN 0020-1669, E-ISSN 1520-510X, Vol. 51, no 9, p. 5070-81Article in journal (Refereed)
    Abstract [en]

    Metal complexation studies were performed with AgSO(3)CF(3) and AgBF(4) and the ditopic pyrimidine-hydrazone ligand 6-(hydroxymethyl)pyridine-2-carboxaldehyde (2-methylpyrimidine-4,6-diyl)bis(1-methylhydrazone) (1) in both CH(3)CN and CH(3)NO(2) in a variety of metal-to-ligand ratios. The resulting complexes were studied in solution by NMR spectroscopy and in the solid state by X-ray crystallography. Reacting either AgSO(3)CF(3) or AgBF(4) with 1 in either CH(3)CN or CH(3)NO(2) in a 1:1 metal-to-ligand ratio produced a double helicate in solution. This double helicate could be converted into a linear complex by increasing the metal-to-ligand ratio; however, the degree of conversion depended on the solvent and counteranion used. Attempts to crystallize the linear AgSO(3)CF(3) complex resulted in crystals with the dimeric structure [Ag(2)1(CH(3)CN)(2)](2)(SO(3)CF(3))(4) (2), while attempts to crystallize the AgSO(3)CF(3) double helicate from CH(3)CN resulted in crystals of another dimeric complex, [Ag(2)1(SO(3)CF(3))(CH(3)CN)(2)](2)(SO(3)CF(3))(2).H(2)O (3). The AgSO(3)CF(3) double helicate was successfully crystallized from a mixture of CH(3)CN and CH(3)NO(2) and had the structure [Ag(2)1(2)](SO(3)CF(3))(2).3CH(3)NO(2) (4). The linear AgBF(4) complex could not be isolated from the double helicate in solution; however, crystals grown from a solution containing both the AgBF(4) double helicate and linear complexes in CH(3)CN had the structure [Ag(2)1(CH(3)CN)(2)](BF(4))(2) (5). The AgBF(4) double helicate could only be crystallized from CH(3)NO(2) and had the structure [Ag(2)1(2)](BF(4))(2).2CH(3)NO(2) (6).

  • 2.
    Hutchinson, Daniel J.
    et al.
    Department of Chemistry, University of Otago.
    Hanton, Lyall R.
    Department of Chemistry, University of Otago.
    Moratti, S. C.
    Department of Chemistry, University of Otago.
    2-Methyl-4,6-bis-(1-methyl-hydrazino)pyrimidine2009In: Acta Crystallographica Section E: Structure Reports Online, ISSN 1600-5368, E-ISSN 1600-5368, Vol. 65, no Pt 7, p. o1546-Article in journal (Refereed)
    Abstract [en]

    In the title compound, C(7)H(14)N(6), the amine groups of the two methyl-hydrazino substituents are orientated in the opposite direction to the methyl substituent at the 2-position of the pyrimidine ring. The mol-ecule is almost planar with only the two amine N atoms lying substanti-ally out of the mean plane of the pyrimidine ring [by 0.1430 (2) and 0.3092 (2) A]. The H atoms on these amine groups point inwards towards the aromatic ring, such that the lone pair of electrons points outwards from the mol-ecule. Each mol-ecule is linked to two others through N-Hcdots, three dots, centeredN hydrogen bonds between the two amino groups, forming a one-dimensional chain in the [010] direction. Offset face-to-face pi-pi stacking inter-actions between the pyrimidine rings organize these chains into a two-dimensional array [centroid-centroid distance = 3.789 (2) A].

  • 3.
    Hutchinson, Daniel J.
    et al.
    Department of Chemistry, University of Otago.
    Hanton, Lyall R.
    Department of Chemistry, University of Otago.
    Moratti, S. C.
    Department of Chemistry, University of Otago.
    Control of self-assembly through the influence of terminal hydroxymethyl groups on the metal coordination of pyrimidine-hydrazone Cu(II) complexes2010In: Inorganic Chemistry, ISSN 0020-1669, E-ISSN 1520-510X, Vol. 49, no 13, p. 5923-34Article in journal (Refereed)
    Abstract [en]

    The synthesis and characterization of 6-hydroxymethylpyridine-2-carboxaldehyde (2-methyl-pyrimidine-4,6-diyl)bis(1-methylhydrazone) (1) is reported. Ligand 1 was designed as a ditopic pyrimidine-hydrazone molecular strand with hydroxymethyl groups attached to the terminal pyridine rings. Coordination of 1 with Cu(ClO(4))(2) x 6 H(2)O or Cu(SO(3)CF(3))(2) x 4 H(2)O in a 1:2 molar ratio resulted in the dinuclear Cu(II) complexes [Cu(2)1(CH(3)CN)(4)](ClO(4))(4) x CH(3)CN (4) and [Cu(2)1(SO(3)CF(3))(2)(CH(3)CN)(2)](SO(3)CF(3))(2) x CH(3)CN (5). X-ray crystallography and (1)H NMR NOESY experiments showed that 1 adopted a horseshoe shape with both pyrimidine-hydrazone (pym-hyz) bonds in a transoid conformation, while 4 and 5 were linear in shape, with both pym-hyz bonds in a cisoid conformation. Coordination of 1 with Cu(ClO(4))(2) x 6 H(2)O or Cu(SO(3)CF(3))(2) x 4 H(2)O in a 1:1 molar ratio resulted in three different bent complexes, [Cu(1H)(ClO(4))(2)](ClO(4)) (6), [Cu(1H)(CH(3)CN)](ClO(4))(3) x 0.5 H(2)O (7), and [Cu1(SO(3)CF(3))](2)(SO(3)CF(3))(2) x CH(3)CN (8), where the pym-hyz bond of the occupied coordination site adopted a cisoid conformation, while the pym-hyz bond of the unoccupied site retained a transoid conformation. Both 6 and 7 showed protonation of the pyridine nitrogen donor in the empty coordination site; complex 8, however, was not protonated. A variety of Cu(II) coordination geometries were seen in structures 4 to 8, including distorted octahedral, trigonal bipyramidal, and square pyramidal geometries. Coordination of the hydroxymethyl arm in the mononuclear Cu(II) complexes 6, 7, and 8 appeared to inhibit the formation of a [2 x 2] grid by blocking further access to the Cu(II) coordination sphere. In addition, the terminal hydroxymethyl groups contributed to the supramolecular structures of the complexes through coordination to the Cu(II) ions and hydrogen bonding.

  • 4.
    Hutchinson, Daniel J.
    et al.
    Department of Chemistry, University of Otago.
    Hanton, Lyall R.
    Department of Chemistry, University of Otago.
    Moratti, S. C.
    Department of Chemistry, University of Otago.
    Influence of terminal acryloyl arms on the coordination chemistry of a ditopic pyrimidine-hydrazone ligand: comparison of Pb(II), Zn(II), Cu(II), and Ag(I) complexes2013In: Inorg Chem, Vol. 52, no 5, p. 2716-28Article in journal (Refereed)
    Abstract [en]

    A new ditopic pyrimidine-hydrazone ligand, 6-hydroxymethylacryloyl-2-pyridinecarboxaldehyde, 2,2'-[2,2'-(2-methyl-4,6-pyrimidinediyl)bis(1-methylhydrazone)] (L2), was synthesized with terminal acryloyl functional groups to allow incorporation into copolymer gel actuators. NMR spectroscopy was used to show that L2 adopted a horseshoe shape with transoid-transoid pym-hyz-py linkages. Metal complexation studies were performed with L2 and salts of Pb(II), Zn(II), Cu(II), and Ag(I) ions in CH3CN in a variety of metal to ligand ratios. Reacting L2 with an excess amount of any of the metal ions resulted in linear complexes where the pym-hyz-py linkages were rotated to a cisoid-cisoid conformation. NMR spectroscopy showed that the acryloyl arms of L2 did not interact with the bound metal ions in solution. Seven of the linear complexes (1-7) were crystallized and analyzed by X-ray diffraction. Most of these complexes (4-7) also showed no coordination between the acryloyl arms and the metal ions; however, complexes 1-3 showed some interactions. Both of the acryloyl arms were coordinated to Pb(II) ions in [Pb2L2(SO3CF3)4] (1), one through the carbonyl oxygen donor and the other through the alkoxy oxygen donor. One of the acryloyl arms of [Cu2L2(CH3CN)3](SO3CF3)4 (2) was coordinated to one of the Cu(II) ions through the carbonyl oxygen donor. There appeared to be a weak association between the alkoxy donors of the acryloyl arms and the Pb(II) ions of [Pb2L2(ClO4)4].CH3CN (3). Reaction of excess AgSO3CF3 with L2 was repeated in CD3NO2, resulting in crystals of {[Ag7(L2)2(SO3CF3)6(H2O)2] SO3CF3}infinity (8), the polymeric structure of which resulted from coordination between the carbonyl donors of the acryloyl arms and the Ag(I) ions. In all cases the coordination and steric effects of the acryloyl arms did not inhibit isomerization of the pym-hyz bonds of L2 or the core shape of the linear complexes.

  • 5.
    Hutchinson, Daniel J.
    et al.
    Department of Chemistry, University of Otago.
    Hanton, Lyall R.
    Department of Chemistry, University of Otago.
    Moratti, S. C.
    Department of Chemistry, University of Otago.
    Metal ion-controlled self-assembly using pyrimidine hydrazone molecular strands with terminal hydroxymethyl groups: a comparison of Pb(II) and Zn(II) complexes2011In: Inorganic Chemistry, ISSN 0020-1669, E-ISSN 1520-510X, Vol. 50, no 16, p. 7637-49Article in journal (Refereed)
    Abstract [en]

    Metal complexation studies were performed with the ditopic pyrimidine-hydrazone (pym-hyz) strand 6-hydroxymethylpyridine-2-carboxaldehyde (2-methyl-pyrimidine-4,6-diyl)bis(1-methylhydrazone) (1) and Pb(ClO(4))(2).3H(2)O, Pb(SO(3)CF(3))(2).H(2)O, Zn(SO(3)CF(3))(2), and Zn(BF(4))(2) to examine the ability of 1 to form various supramolecular architectures. X-ray crystallographic and NMR studies showed that coordination of the Pb(II) salts with 1 on a 2:1 metal/ligand ratio in CH(3)CN and CH(3)NO(2) resulted in the linear complexes [Pb(2)1(ClO(4))(4)] (2), [Pb(2)1(ClO(4))(3)(H(2)O)]ClO(4) (3), and [Pb(2)1(SO(3)CF(3))(3)(H(2)O)]SO(3)CF(3) (4). Two unusually distorted [2 x 2] grid complexes, [Pb1(ClO(4))](4)(ClO(4))(4) (5) and [Pb1(ClO(4))](4)(ClO(4))(4).4CH(3)NO(2) (6), were formed by reacting Pb(ClO(4))(2).6H(2)O and 1 on a 1:1 metal/ligand ratio in CH(3)CN and CH(3)NO(2). These grids formed despite coordination of the hydroxymethyl arms due to the large, flexible coordination sphere of the Pb(II) ions. A [2 x 2] grid complex was formed in solution by reacting Pb(SO(3)CF(3))(2).H(2)O and 1 on a 1:1 metal/ligand ratio in CH(3)CN as shown by (1)H NMR, microanalysis, and ESMS. Reacting the Zn(II) salts with 1 on a 2:1 metal/ligand ratio gave the linear complexes [Zn(2)1(H(2)O)(4)](SO(3)CF(3))(4).C(2)H(5)O (7) and [Zn(2)1(BF(4))(H(2)O)(2)(CH(3)CN)](BF(4))(3).H(2)O (8). (1)H NMR studies showed the Zn(II) and Pb(II) ions in these linear complexes were labile undergoing metal ion exchange. All of the complexes exhibited pym-hyz linkages in their cisoid conformation and binding between the hydroxymethyl arms and the metal ions. No complexes were isolated from reacting either of the Zn(II) salts with 1 on a 1:1 metal/ligand ratio, due to the smaller size of the Zn(II) coordination sphere as compared to the much larger Pb(II) ions.

  • 6.
    Hutchinson, Daniel J.
    et al.
    Department of Chemistry, University of Otago.
    Hanton, Lyall R.
    Department of Chemistry, University of Otago.
    Moratti, S. C.
    Tetratopic pyrimidine-hydrazone ligands modified with terminal hydroxymethyl and acryloyl arms and their Pb(II), Zn(II), Cu(II) and Ag(I) complexes2014In: Dalton Transactions, ISSN 1477-9226, E-ISSN 1477-9234, Vol. 43, no 22, p. 8205-18Article in journal (Refereed)
    Abstract [en]

    The first tetratopic pyrimidine-hydrazone (pym-hyz) molecular strands containing terminal hydroxymethyl (L1) and acryloyl (L2) functional groups have been synthesised. L1 was produced by step-wise imine condensation reactions, starting with 6-hydroxymethyl-2-pyridinecarboxaldehyde. L2 was then synthesised through the treatment of L1 with acryloyl chloride. NMR spectroscopy and X-ray crystallography showed that the ligands adopted a helical shape, comprised of 1 and 1/3 helical turns. Both L1 and L2 uncoiled upon reaction with an excess amount of Pb(II), Zn(II) and Cu(II) ions, resulting in linear M4LA8 complexes (where M = Pb(II), Zn(II), or Cu(II); L = L1 or L2; and A = ClO4(-), SO3CF3(-) or BF4(-)). Horse-shoe shaped Pb2LA4 complexes were also formed by reacting Pb(II) ions with either L1 or L2 in a 2 : 1 metal to ligand ratio. The addition of Ag(I) ions to either L1 or L2 resulted in Ag2L2A2 double helicates, which were stable in the presence of excess Ag(I). The Pb(II), Zn(II) and Ag(I) complexes were characterised by NMR spectroscopy, while UV-Vis spectroscopy was used to probe the Cu(II) complexes. In addition, X-ray crystallography was used to analyse the linear Pb4L1A8, horse-shoe shaped Pb2L1(ClO4)4, twisted Cu3L2(SO3CF3)6, and double helicate Ag2L12(SO3CF3)2 complexes yielding the structures [Pb4L1(ClO4)7(H2O)]ClO4.4CH3NO2 (1), [Pb4L1(SO3CF3)8]2.6CH3CN.H2O (2), [Pb2L1(ClO4)2(CH3CN)(H2O)](ClO4)2.2CH3CN.C4H10O.H2O (3), [Cu3L2(SO3CF3)3(CH3CN)2(H2O)](SO3CF3)3.2CH3CN.H2O (4) and [Ag2L12](SO3CF3)2.CH3CN.H2O (5), respectively.

  • 7.
    Hutchinson, Daniel J.
    et al.
    Department of Chemistry, University of Otago.
    Hanton, Lyall R.
    Department of Chemistry, University of Otago.
    Moratti, Stephen C.
    Department of Chemistry, University of Otago.
    The one pot synthesis of heterobimetallic complexes from a homoditopic pyrimidine–hydrazone ligand2014In: RSC Advances, ISSN 2046-2069, E-ISSN 2046-2069, Vol. 4, no 28, p. 14550-14556Article in journal (Refereed)
    Abstract [en]

    The symmetrical, homoditopic, pyrimidine-hydrazone (pym-hyz) ligand L1 was used to synthesise three new heterobimetallic complexes, CuPbL1(ClO4)4, CuAgL1(SO3CF3)3, and CuZnL1(SO3CF3)4. Each of the complexes was produced in a one-pot reaction in CH3CN, and was isolated in high yield and purity simply by precipitation through the addition of diethyl ether. Analysis was carried out by IR, UV-Vis and ESMS spectroscopy, as well as microanalysis. Crystals were also grown for the purposes of X-ray diffraction studies, which yielded the structures [CuPbL1(ClO4)(CH3CN)2(H2O)](ClO4)3(1),[CuAgL1(SO3CF3)(CH3CN)2](SO3CF3)2$CH3CN (2), and CuZnL1(SO3CF3)2(CH3CN)(H2O)](SO3CF3)2$CH3CN (3), all of which were linear complexes containing a Cu(II) ion in one of the pym-hyz-py coordination sites, and either a Pb(II), Ag(I), or Zn(II) ion in the other.

  • 8.
    Hutchinson, Daniel J.
    et al.
    Department of Chemistry, University of Otago.
    James, M. P.
    Department of Chemistry, University of Otago.
    Hanton, Lyall R.
    Department of Chemistry, University of Otago.
    Moratti, S. C.
    Department of Chemistry, University of Otago.
    Metal-induced isomerization of a molecular strand containing contradictory dynamic coordination sites2014In: Inorganic Chemistry, ISSN 0020-1669, E-ISSN 1520-510X, Vol. 53, no 4, p. 2122-32Article in journal (Refereed)
    Abstract [en]

    A new hydroxymethyl terminated pyrimidine-hydrazone (pym-hyz) ligand (L1) was synthesized with a central hyz-pyridine-hyz (hyz-py-hyz) motif replacing the usual hyz-pym-hyz unit, to create a molecular strand that underwent metal-induced isomerization with a minimal net change in ligand length. NMR spectroscopy showed that L1 had a horseshoe shape due to the hyz-py-hyz and pym-hyz bonds adopting transoid conformations. The ligand was successfully reacted with Pb(II), Zn(II), and Ag(I) salts in either CH3CN or CH3NO2 resulting in horseshoe-shaped M(n+)3L1A3n (where A = ClO4(-) or SO3CF3(-)) complexes in the solution phase. Crystals were grown from these solutions, the structures of which were highly dependent on the metal ion and solvent used, and were distinctly different from those seen in solution. The crystals grown from mixtures of Pb(ClO4)2.3H2O and L1 in either CH3CN or CH3NO2 resulted in the horseshoe-shaped [Pb3L1(ClO4)4(H2O)2](ClO4)2.CH3CN (1) complex or the {[Pb3L1(ClO4)4(H2O)](ClO4)2}infinity.CH3NO2 (2) helical coordination polymer, respectively. The horseshoe-shaped [Pb3L1(SO3CF3)6].CH3CN (3) complex was crystallized from a solution of Pb(SO3CF3)2.H2O and L1 in CH3CN, while the crystals grown from the solution of Zn(SO3CF3)2 and L1 in CH3CN consisted of the zigzag-shaped [Zn3L1(H2O)7](SO3CF3)6 (4) complex. The [Ag3(L1)2](SO3CF3)3 (5) double-helicate and the macrocycle-like [Ag6(L1)2](SO3CF3)6 (6) complex were crystallized from solutions of AgSO3CF3 and L1 in either CH3CN or CH3NO2, respectively.

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