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Chiral metal phosphonates: assembly, structures and functions

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  • ReceivedJan 2, 2020
  • AcceptedFeb 18, 2020
  • PublishedApr 14, 2020

Abstract

As an important class of inorganic-organic hybrid materials, metal phosphonates can exhibit versatile structures, interesting functions and high water and thermal stabilities. Despite a large number of metal phosphonates reported in the past two decades, the development of chiral metal phosphonates is still in its infancy. This review summarizes the current status in this topical field including the synthetic strategies, the crystal structures of chiral metal phosphonates reported thus far, and their physical and chemical properties. Future challenges in this promising field are also discussed.


Funded by

the National Natural Science Foundation of China(21731003,91956102)


Acknowledgment

This work was supported by the National Natural Science Foundation of China (21731003, 91956102).


Interest statement

The authors declare that they have no conflict of interest.


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  • Scheme 1

    Molecular structures of 2-cppH2, 4-cnappH3 and 2-pmampH2, 1,3-pbpH4, 2,5-tbpH4 and ppaH3.

  • Figure 1

    (a) The inorganic layer and (b) packing diagram of structure (VO)3(2-cpp)2(H2O)6•H2O (1), adapted with permission from Ref. [29], copyright by Royal Society of Chemistry (2012) (color online).

  • Scheme 2

    Molecular structures of H3L1, H3L2, ppapH3 and pmpcH3.

  • Figure 2

    (a) Inorganic chain structure (b) packing diagram of compound Co2(4-cnapp)(OH)(H2O)2 (3), adapted with permission from Ref. [33], copyright by American Chemical Society (2016) (color online).

  • Scheme 3

    Molecular structures of pempH2 and cyampH2.

  • Figure 3

    (a) One layer structure of Mn(2-pmamp)(H2O) (4) viewed along the c axis; (b) right-handed helical chain running along the b-axis, adapted with permission from Ref. [34], copyright by American Chemical Society (2008) (color online).

  • Scheme 4

    Molecular structures of binaphthalene-6,6¢-bisphosphonic acids.

  • Figure 4

    (a) Packing diagram of [C4mim][(UO2)2(1,3-pbpH)2•Hmim] (5). (b) A chiral chain of UO6 units and PO3C tetrahedra along the b-axis, adapted with permission from Ref. [35], copyright by Royal Society of Chemistry (2015) (color online).

  • Figure 5

    Packing diagram (a) and inorganic chain (b) of structure Co(2,5-tbpH2)(4,4′-bipy)•H2O (6), adapted with permission from Ref. [36], copyright by American Chemical Society (2016)(color online).

  • Scheme 5

    Molecular structures of Ru complexes of binaphthalene-bisphosphonic acids.

  • Figure 6

    Packing diagrams of structures 9 (a) and 10 (b), adapted with permission from Ref. [18], copyright by Royal Society of Chemistry (2001)(color online).

  • Figure 7

    (a) Single inorganic layer and (b) packing diagram of structure (S)-Zn2{O3PCH2NHC4H7CO2}2 (11). All H atoms are omitted for clarity. Cyan: {ZnO4}, purple: {PO3C}, red: O, grey: C, adapted with permission from Ref. [39], copyright by John Wiley & Sons, Inc. (2004)(color online).

  • Figure 8

    The layer structure of [Zn9(L2)6(H2O)3]•C2H5OH•8.5H2O (16). All C atoms except the carboxylate groups, H atoms except those in water molecules and the lattice solvents are omitted for clarity, adapted with permission from Ref. [44], copyright by Wiley-VCH Verlag GmbH (2009)(color online).

  • Figure 9

    (a) Helical chain in structure [Tb(H2L1)3]•2H2O (17) running along the crystallographic 41 axis; (b) packing diagram of structure 17 viewed along the c-axis, adapted with permission from Ref. [45], copyright by American Chemical Society (2006) (color online).

  • Figure 10

    (a, c) Supramolecular layers made up of hydrogen-bonded cobalt phosphonate chains and (b, d) packing diagrams for (S)-21 (a, b) and (S)-22 (c, d). The red and pink lines represent crystallographically different 4,4′-bpy molecules. Hydrogen bonds are indicated by dotted black lines. The lattice water molecules and phenyl rings are omitted for clarity, adapted with permission from Ref. [46], copyright by Wiley VCH (2015)(color online).

  • Figure 11

    (a) The carboxylate bridged chain and (b) layer structure of Cu(D-pmpcH) (25). (c) The phosphonate bridged chain and (d) 3D framework structure of Cd2(D-pmpcH)(H2O)2Cl2 (26), adapted with permission from Ref. [48], copyright by Royal Society of Chemistry (2017) (color online).

  • Figure 12

    (a) Packing diagram of (R)-α-[Zn2(pemp)(pempH)Cl] (R-27) along the b axis. (b) Coordination geometries of Zn atoms in 27. (c) Inorganic layer of structure R-27, adapted with permission from Ref. [49], copyright by American Chemical Society (2008) (color online).

  • Figure 13

    (a) The building unit of structure R-Fe(pemp)(H2O)2 (R-33); (b) the single nanotube viewed along the c-axis. All H atoms except those attached to N, water O and chiral C atoms are omitted for clarity, adapted with permission from Ref. [52], copyright by Royal Society of Chemistry (2019) (color online).

  • Figure 14

    Interconversion of structures (R)-Mg(pemp)(H2O)2 (34) (left) and (R)-[Mg10(pemp)10(H2O)10]•3H2O (35) (right), adapted with permission from Ref. [53], copyright by Wiley VCH (2017) (color online).

  • Figure 15

    (a) The brick-wall-shaped inorganic layer of S-36. (b) A helical chain within the layer running along the b axis, adapted with permission from Ref. [54], copyright by American Chemical Society (2009) (color online).

  • Figure 16

    Chain structures with atomic labelling in R-39, R-41 and R-40 along the crystallographic 21 or 65 screw axis. The N and C atoms are omitted for clarity, adapted with permission from Ref. [22], copyright by Springer Nature (2017) (color online).

  • Figure 17

    Structural conversion from R-47 and S-47 to R-48 and S-48, respectively, in the presence of NaCl, adapted with permission from Ref. [56], copyright by American Chemical Society (2018) (color online).

  • Figure 18

    Packing diagram of structure (R)-(Me3Sn)2(pemp)(H2O) (R-50), adapted with permission from Ref. [57], copyright by Elsevier (2019)(color online).

  • Figure 19

    (a) The packing diagram and (b) inorganic layer of structure (S)-Co23-OH)(cyamp)(CH3COO) (52), adapted with permission from Ref. [58], copyright by Wiley VCH (2014) (color online).

  • Figure 20

    One layer of structure R-Gd(H2L3)(H3L3)(H2O)4xH2O (R-59), adapted with permission from Ref. [19], copyright by American Chemical Society (2001) (color online).

  • Figure 21

    (a) The inorganic chain and (b) packing diagram of structure R-Co2(H2L3)2(H2O)3•4H2O (64), adapted with permission from Ref. [20], copyright by American Chemical Society (2002) (color online).

  • Figure 22

    (a) The packing diagram and (b) inorganic chain of structure R-[Nd2(HL4)2(MeOH)8]•H4L4•3HCl•6H2O (66), adapted with permission from Ref. [21], copyright by American Chemical Society (2002) (color online).

  • Figure 23

    Chain structure of compound (S,S)-Mn(5-Brsalcy) (2-FC6H4PO3H)]•3H2O (68), adapted with permission from Ref. [59], copyright by Royal Society of Chemistry (2013) (color online).

  • Figure 24

    Proposed formation mechanism of helices. Formation mechanisms of crystalline materials of R-40 (a) and R-39 (b), and helices of R-70 (c), adapted with permission from Ref. [22], copyright by Springer Nature (2017) (color online).

  • Figure 25

    (a, c) Packing diagrams and (b, d) ac magnetic susceptibilities at zero external field for compounds (S)-21 (a, b) and Rac-Co3(ppap)2(4,4′-bpy)2(H2O)2•4H2O (c, d), adapted with permission from Ref. [46], copyright by Wiley-VCH (2015) (color online).

  • Table 1   Enantioenriched metal phosphonates using achiral precursors

    Compound

    Space group

    Structural features

    Ref.

    (VO)3(2-cpp)2(H2O)6•2H2O (1)

    P21

    2D double-layer containing corner-sharing{VO6} or {VO5} and {PO3C}

    [29]

    [Cu(4-cppH)(2,2′-bipy)(H2O)] (2)

    P21

    1D helical chain with {CuN2O3} cross-linked by4-cppH ligands

    [32]

    Co2(4-cnapp)(OH)(H2O)2 (3)

    P212121

    3D framework with Δ-type chain ofCo3(μ3-OH) linked by 4-cnapp ligands

    [33]

    Mn(2-pmamp)(H2O) (4)

    P21

    2D layer with Mn(2-pmamp) connected by{PO3C} via corner-sharing

    [34]

    [C4mim][(UO2)2(1,3-pbpH)2•(Hmim)] (5)

    P212121

    3D framework with the inorganic chainscross-linked by 1,3-pbpH

    [35]

    Co(tbpH2)(4,4′-bipy)•H2O (6)

    P21

    3D framework with the inorganic chainscross-linked by tbpH2 and 4,4′-bipy

    [36]

    Cs(S-HppaH2) (7)

    P212121

    3D framework with {CsOx} polyhedralconnected by {PO3C}

    [37]

  • Table 2   Chiral metal phosphonates obtained using enantiopure phosphonate ligands or co-ligands

    Compound

    Space group

    Structural features

    Ref.

    (R)-α-Zn{O3PCH2P(O)(CH3)(C6H5)}•H2O (R-8)

    P212121

    2D layer containing corner-sharing {ZnO4} and {PO3C}

    [17]

    (R)-α-Zn{O3PCH2P(O)(C2H5)(C6H5)}•H2O (R-9)

    P1

    2D layer containing corner-sharing {ZnO4} and {PO3C}

    [18]

    (R)-α-Zn{O3PCH2P(O)(CH3)(C6H5)}•H2O (R-10)

    C2

    2D layer containing edge-sharing {ZnO6} and {PO3C} linkage

    [18]

    (S)-Zn2{O3PCH2NHC4H7CO2}2 (S-11)

    P21212

    3D framework containing 4,8-nets

    [39]

    (S)-[Co2Cl(HL1)(H2O)5]Cl•H2O (S-12)

    P212121

    3D framework with inorganic chains cross-linked by carboxylate groups

    [42]

    (S)-Sr2(S-HL1)(NO3)2(H2O)•H2O (S-13)

    P212121

    2D layer with edge-sharing {SrOx} chains linked by {PO3C}

    [42]

    Cd2L1Cl(H2O) (14)

    P21

    2D layer with chains of edge-sharing Cd-octahedra linked by {PO3C}

    [43]

    [Zn7L16][Zn(H2O)6]2•16H2O (15)

    P213

    [Zn7L16] clusters packed to create micropore

    [43]

    [Zn9(L2)6(H2O)3]•C2H5OH•8.5H2O (16)

    P1

    2D layer containing Zn7(L)6 clusters and {ZnO4} linkages

    [44]

    [Tb(H2L1)3]•2H2O (17)

    P41

    1D chain with {TbO6} triply bridged by {PO3C}

    [45]

    [Dy(H2L1)3]•2H2O (18)

    P41

    1D chain with {DyO6} triply bridged by {PO3C}

    [45]

    [Eu(H2L1)3]•2H2O (19)

    P41

    1D chain with {EuO6} triply bridged by {PO3C}

    [45]

    [Gd(H2L1)3]•2H2O (20)

    P41

    1D chain with {GdO6} triply bridged by {PO3C}

    [45]

    (S)-Co3(ppap)2(4,4′-bpy)2(H2O)2•4H2O (S-21)

    P21

    3D framework with inorganic chains linked by 4,4′-bpy

    [46]

    (S)-Co3(ppap)2(4,4′-bpy)2(H2O)2•3H2O (S-22)

    P1

    2D layer with inorganic chains linked by 4,4′-bpy

    [46]

    [Ca(D-pmpcH)(H2O)2]•2HO0.5 (23)

    P212121

    2D layer with inorganic chains linked by D-pmpcH ligand

    [47]

    Cu(D-pmpcH)(CH3OH) (24)

    P212121

    1D chain with{CuO4N} connected by carboxylate groups

    [48]

    Cu(D-pmpcH) (25)

    P212121

    2D sheet with (4, 4) topology

    [48]

    Cd2(D-pmpcH)(H2O)2Cl2 (26)

    P212121

    3D framework with cross-linked inorganic chains

    [48]

    (R)-, (S)-α-[Zn2(pemp)(pempH)Cl] (27)

    P212121

    2D layer containing corner-sharing {ZnO3N} or {ZnO3Cl} and {PO3C}

    [49]

    (R)-, (S)-β-[Zn2(pemp)(pempH)Cl] (28)

    P21

    2D layer containing corner-sharing {ZnO3N} or {ZnO3Cl} and {PO3C}

    [49]

    (S)-[Zn4(pempH)4(bdc)2]•2H2O (S-29)

    P21212

    2D layer, inorganic double chains connected by bdc2−

    [50]

    (R)-, (S)-[Zn3(pempH)2(btc)(H2O)2]•H2O (30)

    C2

    3D framework with inorganic chains linked by btc4−

    [50]

    (R)-, (S)-Co(pemp)(H2O)2 (31)

    P63

    1D nanotube containing corner-sharing {CoO5N} and {PO3C}

    [51].

    (R)-, (S)-Ni(pemp)(H2O)2 (32)

    P63

    1D nanotube containing corner-sharing {NiO5N} and {PO3C}

    [51]

    (R)-, (S)-Fe(pemp)(H2O)2 (33)

    P63

    1D nanotube containing corner-sharing {FeO5N} and {PO3C}

    [52]

    (R)-, (S)-Mg(pemp)(H2O)2 (34)

    P63

    1D nanotube containing corner-sharing {MgO5N}and {PO3C}

    [53]

    (R)-[Mg10(pemp)10(H2O)10]•3H2O (R-35)

    P21

    2D layer containing squashed tubes

    [53]

    (S)-Eu(pempH)(NO3)2(H2O)2 (S-36)

    P21

    2D brick-wall-shaped layer of corner-sharing{EuO9} and {PO3C}

    [54]

    (S)-Tb(pempH)(NO3)2(H2O)2 (S-37)

    P21

    2D brick-wall-shaped layer of corner-sharing{TbO9} and {PO3C}

    [54]

    (S)-Ho(pempH)(NO3)2(H2O)2 (S-38)

    P21

    2D brick-wall-shaped layer of corner-sharing {HoO9} and {PO3C}

    [54]

    (R)-(H3O)[Tb3(pempH2)2(pempH)7]

    [Tb3(pempH2)(pempH)8](NO3)4•11H2O (R-39)

    P21

    1D chain with Tb triply bridged by μ3-O(P) and O–P–O units

    [22]

    (R)-, (S)-Tb(pempH)3•2H2O (40)

    P65, P61

    1D chain with Tb triply bridged by two μ3-O(P)and one O–P–O unit

    [22]

    (R)-Tb3(pempH2)2(pempH)7(NO3)2•2H2O (R-41)

    P212121

    1D chain with Tb triply bridged by μ3-O(P) and O–P–O unit

    [22]

    (R)-[Dy3(pempH)7(pempH2)2]2(NO3)4•12H2O (R-42)

    P21

    1D chain with Dy triply bridged by μ3-O(P) and O–P–O unit

    [55]

    (R)-, (S)-[Dy3(pempH)7(pempH2)2]Cl2•2H2O (43)

    P212121

    1D chain with Dy triply bridged by μ3-O(P) and O–P–O unit

    [55]

    (R)-, (S)-[Dy3(pempH)7(pempH2)2]Br2•2H2O (44)

    P212121

    1D chain with Dy triply bridged by μ3-O(P) and O–P–O unit

    [55]

    (R)-[Dy11(pempH2)6(pempH)27](CF3SO3)6•22H2O (R-45)

    P21

    1D chain with Dy triply bridged by μ3-O(P) and O–P–O units

    [55]

    (R)-, (S)-[Er4(pempH)12]•7H2O (46)

    P65, P61

    1D chain containing triple-stranded helices

    [56]

    (R)-, (S)-[Er3(pempH)7(pempH2)2](NO3)2•2H2O (47)

    P212121

    1D chain containing triple-stranded helices

    [56]

    (R)-, (S)-[Er2(pempH)4(NO3)Cl] (48)

    P21212

    1D chain containing quadruple-stranded helices

    [56]

    (R)-[Er2(pempH)4Cl2] (R-49)

    P21212

    1D chain containing quadruple-stranded helices

    [56]

    (R)-, (S)-(Me3Sn)2(pemp)(H2O) (50)

    P21

    1D chain with Me3Sn bridged by O-P-O

    [57]

    (R)-, (S)-(Ph3Sn)2(pemp)2 (51)

    P212121

    1D chain with Ph3Sn bridged by O-P-O

    [57]

    (S)-Co23-OH)(cyamp)(CH3COO) (S-52)

    P21

    2D layer with Δ-type chains of Co33-OH) linked by {PO3C}

    [58]

    (S)-Co23-OH)(cyamp)(C7H15COO) (S-53)

    P21

    2D layer with Δ-type chains of Co33-OH) linked by {PO3C}

    [58]

    (R)-Gd(H2L3)(H3L3)(H2O)4xH2O (R-59)

    P212121

    2D grid with Gd atoms connected by H2L3 and H3L3 ligands

    [19]

    (R)-Ni(H2L3)(MeOH)4 (R-61)

    P212121

    1D chain with Ni atoms connected H2L3 ligands

    [20]

    (R)-Zn3(HL3)2(py)2 (R-62)

    C2

    2D layer with inorganic chains connected by HL3 ligands

    [20]

    (R)-Mn(H2L3)(MeOH)•MeOH (R-63),

    P212121

    3D framework with inorganic chain cross-linked by H2L3 ligands

    [20]

    (R)-Co2(H2L3)2(H2O)3•4H2O (R-64)

    P21

    3D framework with inorganic chain cross-linked by H2L3 ligands

    [20]

    (R)-Cu(L3-Et2) (R-65)

    P212121

    3D framework with inorganic chain cross-linked by L3-Et ligands

    [20]

    (R)-[Nd2(HL4)2(MeOH)8]•H4L4•3HCl•6H2O (R-66)

    C2

    2D layer with inorganic chains linked by HL4 ligands

    [21]

    (R,R)-, (S,S)-Mn(5-Brsalcy)(2-FC6H4PO3H)]•3H2O (68)

    P21

    1D chain with [MnIII(5-Brsalcy)]+ bridged by O-P-O units

    [59]

    (R,R)-[Mn(5-Brsalcy)(4-CH3C6H4PO3H)]•CH3OH•H2O (69)

    P21

    1D chain with [MnIII(5-Brsalcy)]+ bridged by O-P-O units

    [59]

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