Synthesis and Characterization of Some Macrocylic Complexes Incorporating Indole and 2,2'-Bipyridine or 1,10-Phenanthroline

Muhammad S. Khan; Nawal K. Al-Rasbi; Edwin C. Constable

doi:10.24200/squjs.vol20iss1pp20-28

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Apr 28, 2017

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Jun 1, 2015

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Abstract

Complexes of anionic pentadentate macrocyclic ligands by the template condensation of bis(hydrazino)2,2'-bipyridine or 1,10-phenanthroline with an indoledialdehyde have been synthesized. The new Mn(II), Fe(II), Co(II), Ni(II), Cu(II) and Zn(II) macrocyclic complexes have been characterized by analytical and spectroscopic techniques and by conductivity and magnetic susceptibility measurements.

Keywords

Macrocyclic complexes Transition metals Magnetic susceptibility measurements.

References

Lindoy, L.F. The Chemistry of Macrocyclic Ligand Complexes, (Ed), Cambridge University Press, 1990.
Curtis, N. and Melson, G. Coordination Chemistry of Macrocyclic Compounds. Plenum Press, New York, 1979, 230.
Constable, E.C., Sacht, C., Palo, G., Tocher, D.A. and Truter, M.R. Lead(II) as a template for the synthesis of a [1+1] 18-membered hexadentate N4S2-donor macrocycle; crystal and molecular structure of (acetato-O, O′)[3,13-dithia-6,10-diaza-1,8 (2,6)-dipyridinacyclotetradecaphane-6,9-diene] lead(II) hexafluorophosphate. J. Chem. Soc., Dalton Trans., 1993, 8, 1307-1312.
Chung, L., Constable, E.C., Khan, M.S., Lewis, J., Raithby, P.R. and Vargas, M.D. Structural characterisation of a pentagonal bipyramidal macrocyclic chromium (III) complex; an explanation of a chromium-mediated ‘transient-template’ effect. J. Chem. Soc., Chem. Commun., 1984, 21, 1425-1426.
Constable, E.C., Chung, L.-Y., Lewis, J. and Raithby, P.R. The first stable lithium complex of a pentadentate macrocycle incorporating sp2-nitrogen donor atoms only; the X-ray crystal structure of [Li (L2)(MeOH)][PF6]{L2= 6,13-(bis-2-hydroxyethyl)-6H,13H-tripyrido[cd,fg,lm][1,2,4,7,9,10,13] heptazapentadecine. J. Chem. Soc., Chem. Commun., 1986, 23, 1719-1720.
Lewis, J. and Wainwright, K.P. Synthesis of a macrocyclic ligand derived from 6, 6′-dihydrazino-2, 2′-bipyridyl. ibid., 1974, 5, 169-170.
Ansell, C.W.G., Lewis, J., Raithby, P.R., Ramsden, J.N. and Schröder, M. X-Ray crystal structure of the pentagonal bipyramidal nickel(II) complex [Ni II(L)(H2O)2](BF4)2 and the selective stabilisation of the nickel(I) oxidation state by a quinquedentate macrocyclic ligand. ibid., 1982, 10, 546-547.
Bishop, M.M., Lewis, J., O'Donoghue, T.D. and Raithby, P.R. Some metal complexes of macrocyclic ligands incorporating the 1,10-phenanthroline group. X-Ray crystal structure of the manganese(II) complex. ibid., 1978, 11, 476-478.
Bishop, M.M., Lewis, J., O'Donoghue, T.D., Raithby, P.R. and Ramsden, J.N. X-Ray crystal structure of a planar, high-spin iron(II) complex of a pentadentate unsaturated macrocycle formed by reaction of 2,9-di(1-methylhydrazino)-1,10-phenanthroline monohydrochloride with 2,6-diacetylpyridine. ibid., 1978, 19, 828-829.
Chung, L.-Y., Constable, E.C., Dale, A.R., Khan, M.S., Liptrot, M.C., Lewis, J. and Raithby, P.R. The transient template effect: chromium (III)-directed syntheses of metal-free macrocyclic ligands and crystal structure of 1,11-bis(2′-hydroxyethyl)-4,8;12,16;17,21-trinitrilo-1,2,10,11-tetra-azacyclohenicosa-2,4,6,9,12,14,18,20-octaene hydrochloride tetrahydrate. J. Chem. Soc., Dalton Trans., 1990, 4, 1397-1404.
Lewis, J. and Wainwright, K.P. Chemistry of polydentate ligands. Part 2. The mode of co-ordination of 6,6′-dihydrazino-2,2′-bipyridyl ligands with nickel(II) and zinc(II) in octahedral complexes. ibid., 1977, 8, 739-744; Lewis, J. and Wainwright, K.P. Chemistry of polydentate ligands. Part 3. Ring closures effected by the reaction of β-diketones with 6,6′-dihydrazino- and 6,6′-di(N-methylhydrazino)-2,2′-bipyridylnickel(II) diperchlorate. ibid., 1978, 5, 440-446.
Lewis, J., O'Donoghue, T.D., Haque, Z.P. and Tasker, P.A. Chemistry of polydentate ligands. Part 9. Preparation and properties of Group 2B cation complexes with multidentate ligands based on 2,2′-bipyridyl. ibid., 1980, 9, 1664-1667.
Ansell, C.W.G.,Lewis, J.,Raithby, P.R. and Ramsden, J.N. Synthesis and X-ray structure of a macrocyclic pentagonal bipyramidal complex of Cobalt(II). ibid., 1982, 10, 2127-2129.
Ansell, C.W.G., Lewis, J., Liptrot, M.C., Raithby, P.R. and Schröder, M. The stabilisation of low oxidation state transition metal complexes. Preparation and electrochemistry of cobalt(II) unsaturated macrocyclic complexes and the stabilisation of a cobalt(I) derivative. Crystal and molecular structures of [CoII(L)(CH3OH)2][BF4]2 and [CoI(L){P(OCH3)3}][BF4]. ibid., 1982, 8, 1593-1601.
Ansell, C.W.G., Lewis, J., Raithby, P.R. and O'Donoghue, T.D. Synthesis of a macrocyclic metal complex incorporating peripheral hydroxyethyl tails: The X-ray structure of [Mn(L1)Cl][BF4]·4H2O. ibid., 198, 1, 177-179.
Bishop, M.M., Lewis, J., O'Donoghue, T.D., Raithby, P.R. and Ramsden, J.N. Chemistry of polydentate ligands. Part 8. Preparation and properties of iron(II) complexes with quinquedentate macrocyclic ligands. Crystal and molecular structure of a compound where high-spin FeII sits in the ligand cavity. Electrochemistry of a series of complexes with the macrocycles. ibid., 1980, 8, 1390-1396.
Lewis, J., O'Donoghue, T.D. and Raithby, P.R. Chemistry of polydentate ligands. Part 7. Synthesis, characterisation, and properties of some manganese(II) complexes of quinquedentate macrocyclic ligands based on 1,10-phenanthroline. Crystal and molecular structure of a complex with pentagonal-pyramidal coordination geometry about the Mn(II). ibid., 1980, 8,1383-1389.
Lewis, J. and O'Donoghue, T.D. Chemistry of polydentate ligands. Part 5. Complexes of 2,9-di-hydrazino-derivatives of 1,10-phenanthroline. Dependence of co-ordination number of a ligand on the anion present. ibid., 1980, 5, 736-742.
Constable, E.C., Lewis, J., Liptrot, M.C., Raithby, P.R. and Schröder, M. Synthesis, molecular structure and electrochemistry of pentagonal bipyramidal nickel(II) complexes of quinquedentate macrocylic ligand incorporating a 2,2′:6′,2″-terpyridyl moiety. Polyhed., 1983, 2(4), 301-302.
Ansell, C.W.G., Lewis, J., Ramsden, J.N. and Schröder, M. The preparation and electrochemistry of manganese(II) complexes of an unsaturated pentadentate macrocyclic ligand. Polyhed., 1983, 2(6), 489-491.
Constable, E.C.,Corr, S. and Lewis, J. The hydrolytic behaviour of some pentadentate schiff-base type macrocycles. Inorg. Chim. Acta., 1986, 116(2), 95-97.
Constable, E.C.,Khan, M.S.,Liptrot, M.C.,Lewis, J. and Raithby, P.R. Silver(I)-silver (I) interactions in complexes of pentadentate macrocyclic ligands; crystal and molecular structure of [Ag2L2][BF4]2(L1,11-bis (2′-hydroxyethyl)-4, 8; 12, 16; 17, 21-trinitrilo-1, 2, 10, 11-tetraazacyclohenicosa-2,4,6,9,12,14,18,20-octaene). ibid., 1991, 179(2), 239-244.
Constable, E.C.,Khan, M.S.,Lewis, J.,Liptrot, M.C. and Raithby, P.R. Iron complexes of derivatised pentadentate macrocyclic ligands; the crystal and molecular structure of dichloro (6, 13-(bis-2-hydroxyethyl)-6H, 13H-tripyrido [cd, fg, lm][1, 2, 4, 7, 9, 10, 13] heptaaza-pent adecine) iron (III) chloride. ibid., 1991, 181(2), 207-212.
Lewis, J. and Wainwright, K.P. Chemistry of polydentate ligands. Part 4. The oxidative denitrogenation of dichloro-6, 6′-dihydrazino-2, 2′ bipyridyliron (II). ibid., 1979, 34, 57-60; Lewis, J. and O'Donoghue, T. Folding of a macrocyclic ligand induced by hydrogenation of part of the ring: the effect of rigidity in the system. ibid., 1978, 30, L339-L340.
Ansell, C.W.G., Egert, E., Lewis, J. and Raithby, P.R. [2, 9-Bis (N-methylhydrazino)-1, 10-phenanthroline] dichlororhodium (III) tetrafluoroborate sesquihydrate,[ RhCl2 (C14H16N6)]BF4.1.5H2O. Acta Cryst. Sect. C: Cryst. Struct. Commun., 1984, 40(3), 359-362.
Ansell, C.W.G., Lewis, J., Raithby, P.R., Kabir, A., Khan, F.K., Malik, K.M.A., Khan, M.S. and Haider, S.Z. Coordination chemistry of polydentate macrocyclic ligands. Part 1. Synthesis, characterization, spectral, Thermal, electrochemical and electrolytic properties of Ag(I), Pt(II) and Rh(III) Complexes of 2,9-bis(N-methyl hydrazino)-1,10-phenanthroline, L1; crystal and molecular structure of Rh(L1)Cl2.2H20 J. Bangladesh Acad. Sci., 1986, 10, 215-229.
Khan, F.K., Malik, K.M.A., Khan, M.S., Haider, S.Z., Lewis, J., Liptrot, M.C. and Raithby, P.R. Coordination chemistry of polydentate macrocylic ligands. Part 2. Synthesis, characterization, spectral, electrolytic and electrochemical properties of some quinquedentate macrocycles derived from 1,10-phenanthroline dihydrazines and 2,6-pyridine dicarbonyls; crystal structure of a novel N5-macrocycle ibid., 1987, 11, 43-54.
Constable, E.C. and Lewis, J. The preparation and coordination chemistry of 2,2′:6′,2″-terpyridine macrocycles-1. Polyhed.,1982, 1(3), 303-306; Constable, E.C. and Holmes, J.M. The preparation and coordination chemistry of 2,2′:6′,2″-terpyridine macrocycles-VI. Planar hexadentate macrocycles incorporating 2,2′: 6′,2″-terpyridine. ibid., 1988, 7(24), 2531-2536.
Constable, E.C., Lewis, J., Liptrot, M.C. and Raithby, P.R. The preparation and co-ordination chemistry of 2,2′: 6′,2″-terpyridine macrocycles. Part 3. Transient template effects involving dimethyltin(IV). J. Chem. Soc., Dalton Trans., 1984, 10, 2177-2185.
Constable, E.C., Khan, F.K., Lewis, J., Liptrot, M.C. and Raithby, P.R. The preparation and co-ordination chemistry of 2,2′:6′,2″-terpyridine macrocycles. Part 4. Structural characterisation of an intermediate in a transient template reaction. ibid., 1985, 2, 333-335.
Constable, E.C., Holmes, J.M. and McQueen, R.C.S. The preparation and co-ordination chemistry of 2,2′: 6′,2″-terpyridine macrocycles. Part 5. Unsubstituted fifteen-membered-ring macrocycles containing 2,2′: 6′,2′-terpyridine. ibid., 1987, 1, 5-8.
Constable, E.C., Doyle, M.J., Healy, J. and Raithby, P.R. Alkali metal complexes of planar pentadentate macrocycles; a unique environment for lithium in the crystal and molecular structure of (LiL1][PF6] {L1 = 1,6-dimethyl-1,2,5,6-tetra-aza- [6.0.0](2,6)pyridinophane-2,4-diene}. J. Chem. Soc., Chem. Commun., 1988, 18, 1262-1264.
Chung, L., Constable, E.C., Lewis, J., Raithby, P.R. and Kaye, P.T. Transition metal complexes of substituted 2,2′-biquinolines. Part 1. The crystal and molecular structures of [8,8′-bis(aminomethyl)-2,2′-biquinoline]dichloromanganese(II) and [8,8′-bis(aminomethyl)-2,2′-biquinoline]chlorocopper(II) chloride. J. Chem. Soc., Dalton Trans., 1988, 8, 2121-2125.
Constable, E.C., Housecroft, C.E. and Smith, C.B. Self-assembly of two discrete polynuclear iron(II) metallomacrocycles from a ligand containing two 2, 2′:6′,2″-terpyridine binding domains. Inorg. Chem. Commun., 2003, 6(8), 1011-1013.
Chow, H.S., Constable, E.C., Housecroft, C.E. and Neuburger, M. Metal-directed assembly of a conformationally restricted metallomacrocycle. Dalton Trans., 2003, 24, 4568-4569.
Constable, E.C., Dunphy, E.L., Housecroft, C.E., Kylberg, W., Neuburger, M., Schaffner, S., Schofield, E.R. and Smith, C.B. Structural development of free or coordinated 4′-(4-pyridyl)-2, 2′:6′,2′-terpyridine ligands through N-alkylation: New strategies for metallamacrocycle formation. Chem. - A Eur. J., 2006, 12(17), 4600-4610.
Constable, E.C., Housecroft, C.E., Neuburger, M. and Schmitt, C.X. Platinamacrocycles containing 2,5-thiophenediyl and poly(2,5-thiophenediyl)-linked azaaromatic ligands: New structural paradigms for metallosupramolecular chemistry. Polyhedron, 2006, 25(8), 1844-1863.
Constable, E.C. and Schofield, E. Metal-directed assembly of a box-like structure. Chem. Commun., 1998, 3, 403-404.
Constable, E.C., King, A.C. and Raithby, P.R. Synthesis, coordination chemistry and crystal structures of [2+2] macrocycles incorporating 2,6-bis(thiomethyl)pyridine sub-units. Polyhedron, 1998, 17(23-24), 4275-4289.
Constable, E.C. and Housecroft, C.E. Supramolecular approaches to advanced materials. Chimia, 1998, 52(10), 533-538.
Constable, E.C., Harris, K., Housecroft, C.E. and Neuburger, M. When is a metallopolymer not a metallopolymer? When it is a metallomacrocycle? Dalton Trans., 2011, 40(7), 1524-1534.
Constable, E.C., Housecroft, C.E., Prescimone, A.,Vujovic, S. and Zampese, J.A. Environmental control in the assembly of metallomacrocycles and one-dimensional polymers with 4,2′:6′:4′′-terpyridine linkers and zinc(ii) nodes. Cryst. Eng. Comm., 2014, 16(37), 8691-8699.
Black, D.S.C., Rothnie, N.E. and Wong, L.C.H. Synthesis of macrocyclic ligands containing the indole ring system. Tet. Lett., 1980, 21(19), 1883-1886.
Black, D.S.C., Rothnie, N. and Wong, L. Metal template reactions. XX. Macrocyclic metal complexes derived from 4, 6-Dimethoxy-3-methylindole-2, 7-dicarbaldehyde and some primary diamines with additional nitrogen donor atoms. Aust. J. Chem., 1983, 36(12), 2407-2412.
Black, D.S.C., Craig, D.C. and Kumar, N. Synthesis of a new class of indole-containing macrocycles. J. Chem. Soc., Chem. Commun., 1989, 7, 425-426.
Black, D.S.C., Kumar, N. and Wong, L.C.H. Synthesis of macrocyclic nickel(II) complexes containing the 2,2′-bi-indolyl moiety. ibid., 1985, 17, 1174-1175.
Constable, E.C., Khan, M.S. and Lewis, J. Chromium(III) complex of a pentadentate macrocycle containing 2,2’-bipyridine. In Synthetic Methods of Organometallic and Inorganic Chemistry., Hermann, W.A., Salzer, A. (Eds.), Thieme, Stuttgart, 1996, 1, 126.
Constable, E.C., Khan, M.S. and Lewis, J. Chromium(III) directed synthesis of a planar pentadentate macrocycle containing 2,2’-bipyridine. In Synthetic Methods of Organometallic and Inorganic Chemistry., Hermann, W.A., Salzer, A. (Eds.), Thieme, Stuttgart, 1996, 1, 128

References

Lindoy, L.F. The Chemistry of Macrocyclic Ligand Complexes, (Ed), Cambridge University Press, 1990.

Curtis, N. and Melson, G. Coordination Chemistry of Macrocyclic Compounds. Plenum Press, New York, 1979, 230.

Constable, E.C., Sacht, C., Palo, G., Tocher, D.A. and Truter, M.R. Lead(II) as a template for the synthesis of a [1+1] 18-membered hexadentate N4S2-donor macrocycle; crystal and molecular structure of (acetato-O, O′)[3,13-dithia-6,10-diaza-1,8 (2,6)-dipyridinacyclotetradecaphane-6,9-diene] lead(II) hexafluorophosphate. J. Chem. Soc., Dalton Trans., 1993, 8, 1307-1312.

Chung, L., Constable, E.C., Khan, M.S., Lewis, J., Raithby, P.R. and Vargas, M.D. Structural characterisation of a pentagonal bipyramidal macrocyclic chromium (III) complex; an explanation of a chromium-mediated ‘transient-template’ effect. J. Chem. Soc., Chem. Commun., 1984, 21, 1425-1426.

Constable, E.C., Chung, L.-Y., Lewis, J. and Raithby, P.R. The first stable lithium complex of a pentadentate macrocycle incorporating sp2-nitrogen donor atoms only; the X-ray crystal structure of [Li (L2)(MeOH)][PF6]{L2= 6,13-(bis-2-hydroxyethyl)-6H,13H-tripyrido[cd,fg,lm][1,2,4,7,9,10,13] heptazapentadecine. J. Chem. Soc., Chem. Commun., 1986, 23, 1719-1720.

Lewis, J. and Wainwright, K.P. Synthesis of a macrocyclic ligand derived from 6, 6′-dihydrazino-2, 2′-bipyridyl. ibid., 1974, 5, 169-170.

Ansell, C.W.G., Lewis, J., Raithby, P.R., Ramsden, J.N. and Schröder, M. X-Ray crystal structure of the pentagonal bipyramidal nickel(II) complex [Ni II(L)(H2O)2](BF4)2 and the selective stabilisation of the nickel(I) oxidation state by a quinquedentate macrocyclic ligand. ibid., 1982, 10, 546-547.

Bishop, M.M., Lewis, J., O'Donoghue, T.D. and Raithby, P.R. Some metal complexes of macrocyclic ligands incorporating the 1,10-phenanthroline group. X-Ray crystal structure of the manganese(II) complex. ibid., 1978, 11, 476-478.

Bishop, M.M., Lewis, J., O'Donoghue, T.D., Raithby, P.R. and Ramsden, J.N. X-Ray crystal structure of a planar, high-spin iron(II) complex of a pentadentate unsaturated macrocycle formed by reaction of 2,9-di(1-methylhydrazino)-1,10-phenanthroline monohydrochloride with 2,6-diacetylpyridine. ibid., 1978, 19, 828-829.

Chung, L.-Y., Constable, E.C., Dale, A.R., Khan, M.S., Liptrot, M.C., Lewis, J. and Raithby, P.R. The transient template effect: chromium (III)-directed syntheses of metal-free macrocyclic ligands and crystal structure of 1,11-bis(2′-hydroxyethyl)-4,8;12,16;17,21-trinitrilo-1,2,10,11-tetra-azacyclohenicosa-2,4,6,9,12,14,18,20-octaene hydrochloride tetrahydrate. J. Chem. Soc., Dalton Trans., 1990, 4, 1397-1404.

Lewis, J. and Wainwright, K.P. Chemistry of polydentate ligands. Part 2. The mode of co-ordination of 6,6′-dihydrazino-2,2′-bipyridyl ligands with nickel(II) and zinc(II) in octahedral complexes. ibid., 1977, 8, 739-744; Lewis, J. and Wainwright, K.P. Chemistry of polydentate ligands. Part 3. Ring closures effected by the reaction of β-diketones with 6,6′-dihydrazino- and 6,6′-di(N-methylhydrazino)-2,2′-bipyridylnickel(II) diperchlorate. ibid., 1978, 5, 440-446.

Lewis, J., O'Donoghue, T.D., Haque, Z.P. and Tasker, P.A. Chemistry of polydentate ligands. Part 9. Preparation and properties of Group 2B cation complexes with multidentate ligands based on 2,2′-bipyridyl. ibid., 1980, 9, 1664-1667.

Ansell, C.W.G.,Lewis, J.,Raithby, P.R. and Ramsden, J.N. Synthesis and X-ray structure of a macrocyclic pentagonal bipyramidal complex of Cobalt(II). ibid., 1982, 10, 2127-2129.

Ansell, C.W.G., Lewis, J., Liptrot, M.C., Raithby, P.R. and Schröder, M. The stabilisation of low oxidation state transition metal complexes. Preparation and electrochemistry of cobalt(II) unsaturated macrocyclic complexes and the stabilisation of a cobalt(I) derivative. Crystal and molecular structures of [CoII(L)(CH3OH)2][BF4]2 and [CoI(L){P(OCH3)3}][BF4]. ibid., 1982, 8, 1593-1601.

Ansell, C.W.G., Lewis, J., Raithby, P.R. and O'Donoghue, T.D. Synthesis of a macrocyclic metal complex incorporating peripheral hydroxyethyl tails: The X-ray structure of [Mn(L1)Cl][BF4]·4H2O. ibid., 198, 1, 177-179.

Bishop, M.M., Lewis, J., O'Donoghue, T.D., Raithby, P.R. and Ramsden, J.N. Chemistry of polydentate ligands. Part 8. Preparation and properties of iron(II) complexes with quinquedentate macrocyclic ligands. Crystal and molecular structure of a compound where high-spin FeII sits in the ligand cavity. Electrochemistry of a series of complexes with the macrocycles. ibid., 1980, 8, 1390-1396.

Lewis, J., O'Donoghue, T.D. and Raithby, P.R. Chemistry of polydentate ligands. Part 7. Synthesis, characterisation, and properties of some manganese(II) complexes of quinquedentate macrocyclic ligands based on 1,10-phenanthroline. Crystal and molecular structure of a complex with pentagonal-pyramidal coordination geometry about the Mn(II). ibid., 1980, 8,1383-1389.

Lewis, J. and O'Donoghue, T.D. Chemistry of polydentate ligands. Part 5. Complexes of 2,9-di-hydrazino-derivatives of 1,10-phenanthroline. Dependence of co-ordination number of a ligand on the anion present. ibid., 1980, 5, 736-742.

Constable, E.C., Lewis, J., Liptrot, M.C., Raithby, P.R. and Schröder, M. Synthesis, molecular structure and electrochemistry of pentagonal bipyramidal nickel(II) complexes of quinquedentate macrocylic ligand incorporating a 2,2′:6′,2″-terpyridyl moiety. Polyhed., 1983, 2(4), 301-302.

Ansell, C.W.G., Lewis, J., Ramsden, J.N. and Schröder, M. The preparation and electrochemistry of manganese(II) complexes of an unsaturated pentadentate macrocyclic ligand. Polyhed., 1983, 2(6), 489-491.

Constable, E.C.,Corr, S. and Lewis, J. The hydrolytic behaviour of some pentadentate schiff-base type macrocycles. Inorg. Chim. Acta., 1986, 116(2), 95-97.

Constable, E.C.,Khan, M.S.,Liptrot, M.C.,Lewis, J. and Raithby, P.R. Silver(I)-silver (I) interactions in complexes of pentadentate macrocyclic ligands; crystal and molecular structure of [Ag2L2][BF4]2(L1,11-bis (2′-hydroxyethyl)-4, 8; 12, 16; 17, 21-trinitrilo-1, 2, 10, 11-tetraazacyclohenicosa-2,4,6,9,12,14,18,20-octaene). ibid., 1991, 179(2), 239-244.

Constable, E.C.,Khan, M.S.,Lewis, J.,Liptrot, M.C. and Raithby, P.R. Iron complexes of derivatised pentadentate macrocyclic ligands; the crystal and molecular structure of dichloro (6, 13-(bis-2-hydroxyethyl)-6H, 13H-tripyrido [cd, fg, lm][1, 2, 4, 7, 9, 10, 13] heptaaza-pent adecine) iron (III) chloride. ibid., 1991, 181(2), 207-212.

Lewis, J. and Wainwright, K.P. Chemistry of polydentate ligands. Part 4. The oxidative denitrogenation of dichloro-6, 6′-dihydrazino-2, 2′ bipyridyliron (II). ibid., 1979, 34, 57-60; Lewis, J. and O'Donoghue, T. Folding of a macrocyclic ligand induced by hydrogenation of part of the ring: the effect of rigidity in the system. ibid., 1978, 30, L339-L340.

Ansell, C.W.G., Egert, E., Lewis, J. and Raithby, P.R. [2, 9-Bis (N-methylhydrazino)-1, 10-phenanthroline] dichlororhodium (III) tetrafluoroborate sesquihydrate,[ RhCl2 (C14H16N6)]BF4.1.5H2O. Acta Cryst. Sect. C: Cryst. Struct. Commun., 1984, 40(3), 359-362.

Ansell, C.W.G., Lewis, J., Raithby, P.R., Kabir, A., Khan, F.K., Malik, K.M.A., Khan, M.S. and Haider, S.Z. Coordination chemistry of polydentate macrocyclic ligands. Part 1. Synthesis, characterization, spectral, Thermal, electrochemical and electrolytic properties of Ag(I), Pt(II) and Rh(III) Complexes of 2,9-bis(N-methyl hydrazino)-1,10-phenanthroline, L1; crystal and molecular structure of Rh(L1)Cl2.2H20 J. Bangladesh Acad. Sci., 1986, 10, 215-229.

Khan, F.K., Malik, K.M.A., Khan, M.S., Haider, S.Z., Lewis, J., Liptrot, M.C. and Raithby, P.R. Coordination chemistry of polydentate macrocylic ligands. Part 2. Synthesis, characterization, spectral, electrolytic and electrochemical properties of some quinquedentate macrocycles derived from 1,10-phenanthroline dihydrazines and 2,6-pyridine dicarbonyls; crystal structure of a novel N5-macrocycle ibid., 1987, 11, 43-54.

Constable, E.C. and Lewis, J. The preparation and coordination chemistry of 2,2′:6′,2″-terpyridine macrocycles-1. Polyhed.,1982, 1(3), 303-306; Constable, E.C. and Holmes, J.M. The preparation and coordination chemistry of 2,2′:6′,2″-terpyridine macrocycles-VI. Planar hexadentate macrocycles incorporating 2,2′: 6′,2″-terpyridine. ibid., 1988, 7(24), 2531-2536.

Constable, E.C., Lewis, J., Liptrot, M.C. and Raithby, P.R. The preparation and co-ordination chemistry of 2,2′: 6′,2″-terpyridine macrocycles. Part 3. Transient template effects involving dimethyltin(IV). J. Chem. Soc., Dalton Trans., 1984, 10, 2177-2185.

Constable, E.C., Khan, F.K., Lewis, J., Liptrot, M.C. and Raithby, P.R. The preparation and co-ordination chemistry of 2,2′:6′,2″-terpyridine macrocycles. Part 4. Structural characterisation of an intermediate in a transient template reaction. ibid., 1985, 2, 333-335.

Constable, E.C., Holmes, J.M. and McQueen, R.C.S. The preparation and co-ordination chemistry of 2,2′: 6′,2″-terpyridine macrocycles. Part 5. Unsubstituted fifteen-membered-ring macrocycles containing 2,2′: 6′,2′-terpyridine. ibid., 1987, 1, 5-8.

Constable, E.C., Doyle, M.J., Healy, J. and Raithby, P.R. Alkali metal complexes of planar pentadentate macrocycles; a unique environment for lithium in the crystal and molecular structure of (LiL1][PF6] {L1 = 1,6-dimethyl-1,2,5,6-tetra-aza- [6.0.0](2,6)pyridinophane-2,4-diene}. J. Chem. Soc., Chem. Commun., 1988, 18, 1262-1264.

Chung, L., Constable, E.C., Lewis, J., Raithby, P.R. and Kaye, P.T. Transition metal complexes of substituted 2,2′-biquinolines. Part 1. The crystal and molecular structures of [8,8′-bis(aminomethyl)-2,2′-biquinoline]dichloromanganese(II) and [8,8′-bis(aminomethyl)-2,2′-biquinoline]chlorocopper(II) chloride. J. Chem. Soc., Dalton Trans., 1988, 8, 2121-2125.

Constable, E.C., Housecroft, C.E. and Smith, C.B. Self-assembly of two discrete polynuclear iron(II) metallomacrocycles from a ligand containing two 2, 2′:6′,2″-terpyridine binding domains. Inorg. Chem. Commun., 2003, 6(8), 1011-1013.

Chow, H.S., Constable, E.C., Housecroft, C.E. and Neuburger, M. Metal-directed assembly of a conformationally restricted metallomacrocycle. Dalton Trans., 2003, 24, 4568-4569.

Constable, E.C., Dunphy, E.L., Housecroft, C.E., Kylberg, W., Neuburger, M., Schaffner, S., Schofield, E.R. and Smith, C.B. Structural development of free or coordinated 4′-(4-pyridyl)-2, 2′:6′,2′-terpyridine ligands through N-alkylation: New strategies for metallamacrocycle formation. Chem. - A Eur. J., 2006, 12(17), 4600-4610.

Constable, E.C., Housecroft, C.E., Neuburger, M. and Schmitt, C.X. Platinamacrocycles containing 2,5-thiophenediyl and poly(2,5-thiophenediyl)-linked azaaromatic ligands: New structural paradigms for metallosupramolecular chemistry. Polyhedron, 2006, 25(8), 1844-1863.

Constable, E.C. and Schofield, E. Metal-directed assembly of a box-like structure. Chem. Commun., 1998, 3, 403-404.

Constable, E.C., King, A.C. and Raithby, P.R. Synthesis, coordination chemistry and crystal structures of [2+2] macrocycles incorporating 2,6-bis(thiomethyl)pyridine sub-units. Polyhedron, 1998, 17(23-24), 4275-4289.

Constable, E.C. and Housecroft, C.E. Supramolecular approaches to advanced materials. Chimia, 1998, 52(10), 533-538.

Constable, E.C., Harris, K., Housecroft, C.E. and Neuburger, M. When is a metallopolymer not a metallopolymer? When it is a metallomacrocycle? Dalton Trans., 2011, 40(7), 1524-1534.

Constable, E.C., Housecroft, C.E., Prescimone, A.,Vujovic, S. and Zampese, J.A. Environmental control in the assembly of metallomacrocycles and one-dimensional polymers with 4,2′:6′:4′′-terpyridine linkers and zinc(ii) nodes. Cryst. Eng. Comm., 2014, 16(37), 8691-8699.

Black, D.S.C., Rothnie, N.E. and Wong, L.C.H. Synthesis of macrocyclic ligands containing the indole ring system. Tet. Lett., 1980, 21(19), 1883-1886.

Black, D.S.C., Rothnie, N. and Wong, L. Metal template reactions. XX. Macrocyclic metal complexes derived from 4, 6-Dimethoxy-3-methylindole-2, 7-dicarbaldehyde and some primary diamines with additional nitrogen donor atoms. Aust. J. Chem., 1983, 36(12), 2407-2412.

Black, D.S.C., Craig, D.C. and Kumar, N. Synthesis of a new class of indole-containing macrocycles. J. Chem. Soc., Chem. Commun., 1989, 7, 425-426.

Black, D.S.C., Kumar, N. and Wong, L.C.H. Synthesis of macrocyclic nickel(II) complexes containing the 2,2′-bi-indolyl moiety. ibid., 1985, 17, 1174-1175.

Constable, E.C., Khan, M.S. and Lewis, J. Chromium(III) complex of a pentadentate macrocycle containing 2,2’-bipyridine. In Synthetic Methods of Organometallic and Inorganic Chemistry., Hermann, W.A., Salzer, A. (Eds.), Thieme, Stuttgart, 1996, 1, 126.

Constable, E.C., Khan, M.S. and Lewis, J. Chromium(III) directed synthesis of a planar pentadentate macrocycle containing 2,2’-bipyridine. In Synthetic Methods of Organometallic and Inorganic Chemistry., Hermann, W.A., Salzer, A. (Eds.), Thieme, Stuttgart, 1996, 1, 128

Synthesis and Characterization of Some Macrocylic Complexes Incorporating Indole and 2,2'-Bipyridine or 1,10-Phenanthroline

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