Formation of Lanthanide (III)-Containing Metallosupramolecular

Article pubs.acs.org/crystal

Formation of Lanthanide(III)-Containing Metallosupramolecular Arrays Induced by Tris(spiroborate) Twin Bowl Hiroshi Danjo,*,† Toshi Nakagawa,† Kosuke Katagiri,† Masatoshi Kawahata,‡ Seiki Yoshigai,‡ Toshifumi Miyazawa,† and Kentaro Yamaguchi‡ †

Department of Chemistry, and Graduate School of Natural Science, Konan University, 8-9-1 Okamoto, Higashinada, Kobe 658-8501, Japan ‡ Kagawa School of Pharmaceutical Sciences, Tokushima Bunri University, 1314-1 Shido, Sanuki, Kagawa 769-2193, Japan S Supporting Information *

ABSTRACT: Lanthanide(III)-containing metallosupramolecular arrays were prepared in the crystalline state simply by mixing trifluoromethanesulfonate salts of yttrium(III), lanthanum(III), europium(III), terbium(III), erbium(III), and ytterbium(III) with a rac-tris(spiroborate) twin bowl in N,Ndimethylformamide (DMF). In the crystal, the lanthanide(III) ion coordinated to eight or nine DMF molecules to form spherical tricationic complexes, and the spiroborate twin bowl iteratively glued the complexes to each other to form onedimensional arrays that were unidirectionally packed in the crystal. In each case, the array structure was stabilized by many aromatic C−H···π interactions and C−H···O hydrogen bonds between the twin bowls and the lanthanide(III) complexes. Among the lanthanide(III) ions, yttrium(III), terbium(III), erbium(III), and ytterbium(III) gave almost the same crystal lattice and packing, whereas a different array structure and crystal packing was observed when lanthanum(III) and europium(III) were used, probably due to the difference of the ionic radii of the lanthanide(III) ions.

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INTRODUCTION Continuing attention has been paid to the development of lanthanide(III)-containing materials because of their attractive chemical and physical properties, such as catalysis, luminescence, magnetics, etc., and for this purpose, various lanthanide(III)-containing compounds have been developed so far.1 Among them, coordination polymers and metal−organic frameworks (MOF) are effective for the ordered accumulation of lanthanide(III) ions because of their accessibility and structural diversity, and their properties are well documented.2 In our previous report, we have demonstrated that the backto-back twin-bowl-shaped tris(spiroborate) cyclophane (1· (Me2NH2)3) could be prepared from tetrahydroxybinaphthyl and boric acid in a self-organization manner (Figure 1).3a Those twin bowls simultaneously recognized two guests in the bowl-shaped cavities at both sides of their symmetry plane, and formed a supramolecular chain structure in the presence of a spherical ditopic cationic guest, such as [Ir(tpy)2]3+ (tpy: 2,2′:6′,2″-terpyridine), in solution and the crystalline state. In the crystal, [Ir(tpy)2]3+ cations were glued to each other to form a one-dimensional array, and all the arrays were lined up in a single direction. A similar supramolecular one-dimensional array was also observed in the cocrystal of spiroborate twin bowl, potassium cation, and [Fe(tpy)2]2+.3b These intriguing results led us to conclude that the spiroborate twin bowls acted as molecular connecting modules to induce the formation of © XXXX American Chemical Society

Figure 1. Chemical diagram of spiroborate twin bowls 1·(Me2NH2)3 and 2·(Me2NH2)3.

supramolecular one-dimensional arrays in the presence of various guest compounds. As the next step, we planned to apply our “twin bowl” strategy to the accumulation of lanthanide cations. Herein, we present an easy approach to metallosupramolecular onedimensional arrays containing lanthanide(III) via the multicomponent self-organization method (Figure 2). In this system, Received: October 1, 2014 Revised: October 28, 2014

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dx.doi.org/10.1021/cg5014686 | Cryst. Growth Des. XXXX, XXX, XXX−XXX

Crystal Growth & Design

Article

octacoordinated yttrium(III) complex.5,6 The [Y(dmf)8]3+ complex was then glued to each other by the ditopic molecular recognition of 13−. Here, C−H···π interactions were found between the four methyl groups of coordinated DMF and the naphthalene rings of both sides of 13− at the aromatic centroid distance of 2.654−3.255 Å. In addition, C−H···O hydrogen bonds were observed between the two methyl groups of the coordinated DMF and the six oxygen atoms of the spiroborate linkages, which were located inside the central cavity of 13−. The bond lengths of the C−H···O(borate) hydrogen bonds were distributed from 2.359 to 2.820 Å. The hydrogen bonds would be strengthened by the electrostatic effect arising from the electron-deficient DMF ligands and the anionically charged spiroborate oxygens. As a result of the multidentate host−guest interactions, twin bowl 13− and [Y(dmf)8]3+ iteratively recognized each other to form an infinite metallosupramolecular array (Figure 3b).3 This array extended almost along the D3 axis of twin bowl 13− (the angle between the a axis and the D3 axis of 13− determined by three boron atoms was ca. 10°), and the distance between the two adjacent yttrium centers was 14.7857 Å (corresponding to the lattice constant of the a axis). The two yttrium(III) complexes were sufficiently close to have a van der Waals contact and to penetrate the central crown-ether-like cavity of 13− (the distance between the two methyl carbons of DMF ligands on both sides of 13− was estimated to be 3.825 Å). All the twin bowls in a single array had the same absolute configuration, and arrays of the same configuration were lined up along the b axis (Figure 3c). Between the two 13− in the adjacent array, aromatic C−H···π interactions were observed (2.835 and 3.072 Å of the aromatic centroid distance), whereas aromatic C−H···O(borate) hydrogen bonds were found between the two 13− with the opposite configuration (2.814 Å of the distance). The one-dimensional metallosupramolecular arrays were bound to each other through those interactions to form a unidirectionally oriented columnar structure. The metallosupramolecular array formation of the spiroborate twin bowl and yttrium(III) cation was also confirmed in the solution phase by dynamic light scattering (DLS) experiment in chloroform (Figure S15, Supporting Information). Spiroborate twin bowl 2·(Me2NH2)3, bearing n-octyl groups at the 6-position of naphthalene rings, gave an averaged

a cationic guest complex is in situ constructed from a lanthanide(III) cation and a small monodentate ligand, such as N,N-dimethylformamide (DMF), which is then iteratively recognized by a spiroborate twin bowl to form a supramolecular array.

Figure 2. Schematic representation of the formation of a metallosupramolecular array induced by spiroborate twin bowl.

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RESULTS AND DISCUSSION Yttrium(III)-Containing Metallosupramolecular OneDimensional Array. The preparation of the lanthanidecontaining supramolecular array was carried out by mixing rac1·(Me2NH2)3 with yttrium(III) trifluoromethanesulfonate (Y(OTf)3) in DMF at room temperature. The spontaneous formation of pale yellow prismatic crystals was observed. Single-crystal X-ray diffraction analysis revealed that the 1:1 host−guest complex of spiroborate twin bowl 13− and yttrium(III) cation was constructed to form an infinite onedimensional supramolecular structure (Figure 3). In this cocrystal, the eight DMF molecules coordinated to the yttrium(III) center in a square-antiprismatic geometry to form a spherical cationic complex (Figure 3a).4 The averaged Y···O coordination bond length was estimated to be 2.343 Å, which was considered to be common for this type of

Figure 3. (a) Side view of 1·[Y(dmf)8] drawn with adjacent [Y(dmf)8]3+. C−H···π interactions are shown by dashed yellow lines and C−H··· O(borate) hydrogen bonds, by dashed green lines. (b) The molecular structure of the metallosupramolecular array of 1·[Y(dmf)8]. 13− is shown by a black wire, and [Y(dmf)8]3+ is drawn in the space-filling representation. (c) The packing diagram of 1·[Y(dmf)8] along the a axis. Metallosupramolecular arrays composed of each enantiomer are drawn in blue and pink, respectively. Twin bowl 13− is drawn in stick representation and [Y(dmf)8]3+ in wire representation. Intermolecular interactions between adjacent 13− are shown by dashed black lines. Free DMF molecules are omitted for clarity. B



Article

On the other hand, completely different crystal lattices were obtained with lanthanum(III) and europium(III) (Table 2). The single crystal of 1·[Eu(dmf)8] was prepared by mixing rac1·(Me2NH2)3 with an equimolar amount of europium(III) trifluoromethanesulfonate in DMF. In the crystal, the metallosupramolecular array was extended along the [1̅01] direction of the lattice, and the averaged repeating unit length of the array was estimated to be 14.552 Å (Figure 5a). The D3 axis of twin bowl 13− (determined by three boron atoms) was tilted by ca. 28° from the array direction. The europium(III) center had an antiprismatic octacoordination geometry, and the averaged Eu···O coordination bond length was 2.396 Å. In contrast to other lanthanide(III) ions, both enantiomers of 13− were alternately lined up in a single array. Intermolecular interactions between 13− and [Eu(dmf)8]3+ were again observed not only inside the bowl-shaped cavity of 13− in the same array but also outside the cavity of 13− of the adjacent arrays (Figure 5b). As the intra-array interactions, eight C−H···O(borate) hydrogen bonds between the methyl group of the DMF ligand and inside oxygens of the crown-ether-like cavity were observed, the lengths of which were 2.465−2.828 Å. In addition, five C−H···π contacts in the range of 2.596−3.251 Å of the aromatic centroid distance were found between the methyl groups of DMF ligands and the naphthyl groups of 13−. Three other C−H···π interactions in the range of 2.707−3.113 Å of the centroid distance were also noted between [Eu(dmf)8]3+ and 13− in an adjacent array. The cocrystal of lanthanum(III) and spiroborate twin bowl 13− was obtained by vapor diffusion crystallization of the DMF solution of lanthanum(III) trifluoromethanesulfonate and 1· (Me2NH2)3 with diethyl ether. The crystal had a P1̅ space group and also gave an array structure that extended along the a axis of the unit cell. It was noted that the lanthanum(III) center required nine DMF ligands to form [La(dmf)9]3+ with a tricapped trigonal prismatic geometry,4 and the averaged La···O coordination bond length was determined to be 2.557 Å. The length of the repeating unit of the array was 14.596 Å (corresponding to the a axis), and in this case as well, many host−guest interactions were observed. The twelve C−H··· O(borate) hydrogen bonds and the eight C−H···π contacts were observed as intra-array interactions in the ranges of 2.295−2.876 and 2.803−3.021 Å (aromatic centroid distance), respectively (Figure 6a). As interarray interactions, four C−H··· O(borate) hydrogen bonds (2.572−2.730 Å) and two C−H···π contacts (2.875 and 3.003 Å (centroid distance)) were observed between [La(dmf)9]3+ and four molecules of 13− in the adjacent arrays. In addition, four C−H···O(borate) hydrogen bonds (2.594 and 2.709 Å) and four C−H···π contacts (2.890 and 2.935 Å (centroid distance)) were found between adjacent 13−. Each array was composed of 13− with a single chirality, in the same manner as that of yttrium(III), terbium(III), erbium(III), and ytterbium(III). Ligand Exchange in Yttrium(III)-Containing Metallosupramolecular Array. The DMF ligands on lanthanide(III) in the metallosupramolecular array could be exchanged with other ligands, such as pyridine N-oxide (PyO).7 The crystallization was carried out from the 1:1 DMF solution of rac-1·(Me2NH2)3 and Y(OTf)3 in the presence of 100 equiv of PyO. A similar metallosupramolecular polymer structure was also observed by X-ray diffraction analysis (Figure 7). In the crystal structure, two of the eight DMF ligands on each yttrium(III) center were exchanged with PyO. It should be noted that there was almost no change of the crystal packing

hydrodynamic diameter (DH) of 1.64 nm, which well-agreed with that estimated by the crystal structure of 1·(Me2NH2)3.3a On the other hand, 2·[Y(dmf)8], obtained from the mixture of an equimolar mixture of 2·(Me2NH2)3 and Y(OTf)3 in DMF and isolated by reprecipitation with methanol, afforded an averaged DH of 3.42 nm, and this value was diminished to 1.68 nm by the addition of barium trifluoromethanesulfonate. This implied that the short supramolecular array structure was maintained in chloroform solution, and that was dissociated by the addition of barium cation, which caused the off balance of the countercharge in host−guest complexation.3b Supramolecular One-Dimensional Array Composed of Other Lanthanide(III) Cations. This multicomponent construction of metallosupramolecular arrays in the crystalline state was also observed in twin bowl 13− and other lanthanide(III) ions, including lanthanum(III), europium(III), terbium(III), erbium(III), and ytterbium(III). Among them, terbium(III), erbium(III), and ytterbium(III) gave similar single crystals simply by mixing their trifluoromethanesulfonate salts with an equimolar amount of rac-1·(Me2NH2)3 in DMF, and in those crystals, almost the same crystal lattices and molecular structures as those of yttrium(III) were observed (Figure 4).

Figure 4. Crystal packing of 1·[Y(dmf)8] (a), 1·[Tb(dmf)8] (b), 1· [Er(dmf)8] (c), and 1·[Yb(dmf)8] (d). Each diagram is shown along the a axis. Free DMF molecules are omitted for clarity.

In each crystal shown in Table 1, the metallosupramolecular arrays were extended along the a axis, and therefore, the length of the a axis corresponded to the length of the repeating unit of the arrays. The longest a axis (14.838 Å) was measured in the terbium(III) crystal, whereas the ytterbium(III) crystal gave the shortest a axis (14.7773 Å). This difference would be derived from the size of the guest complex [Ln(dmf)8]3+, which was determined by the ionic radius of the central lanthanide(III) ion (1.040 Å for terbium(III) ion, 1.004 Å for erbium(III) ion, and 0.985 Å for ytterbium(III) ion). C



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Table 1. Unit Cell Parameters for Crystals of Y(III)-, Tb(III)-, Er(III)-, and Yb(III)-Containing Metallosupramolecular Arrays of 13− space group a (Å) b (Å) c (Å) α (deg) β (deg) γ (deg) cell volume Z coordination number averaged Ln(III)···O distance (Å) ionic radius (Å)

Y(III)

Tb(III)

Er(III)

Yb(III)

P1̅ 14.7857(10) 15.1728(11) 23.9999(17) 75.5080(10) 77.6760(10) 66.1820(10) 4730.3(6) 2 8 2.343 1.019

P1̅ 14.838(5) 15.175(5) 24.032(5) 75.638(5) 77.766(5) 66.201(5) 4758(2) 2 8 2.369 1.040

P1̅ 14.805(5) 15.194(5) 24.021(5) 75.477(5) 77.533(5) 66.128(5) 4743(2) 2 8 2.338 1.004

P1̅ 14.7773(9) 15.2028(9) 23.9870(14) 75.4380(10) 77.5750(10) 66.1860(10) 4732.2(5) 2 8 2.317 0.985

Table 2. Unit Cell Parameters for Crystals of Y(III)-, La(III)-, and Eu(III)-Containing Metallosupramolecular Arrays of 13− space group a (Å) b (Å) c (Å) α (deg) β (deg) γ (deg) cell volume Z coordination number averaged Ln(III)···O distance (Å) ionic radius (Å)

Y(III)

La(III)

Eu(III)

P1̅ 14.7857(10) 15.1728(11) 23.9999(17) 75.5080(10) 77.6760(10) 66.1820(10) 4730.3(6) 2 8 2.343 1.019

P1̅ 14.596(3) 18.269(4) 19.118(4) 85.26(3) 74.40(3) 68.06(3) 4553.4(19) 2 9 2.557 1.216

P21/n 11.896(5) 28.247(11) 24.600(10) 90 99.322(5) 90 8156(6) 4 8 2.396 1.066

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CONCLUSION

The metallosupramolecular array formation induced by spiroborate twin bowl 13− was examined with various lanthanide(III) cations, including yttrium(III), lanthanum(III), europium(III), terbium(III), erbium(III), and ytterbium(III), in DMF, and in all cases, unidirectional array formation was achieved in the crystalline state. Those lanthanide(III) ions except lanthanum(III) took a square-antiprismatic octacoordination geometry to form a spherical cationic guest, [Ln(dmf)8]3+, in the iterative host−guest system. This complexation behavior of lanthanide(III) ions was preserved after exchanging two DMF ligands with PyO. These results indicate that the spiroborate strategy for the metalloarray formation is quite common for a range of lanthanide(III) cations and ligands. Particularly, in the case of yttrium(III), terbium(III), erbium(III), and ytterbium(III), almost the same crystal packing was observed in DMF. On the other hand, lanthanum(III) and europium(III) exhibited different crystallization behavior. The supramolecular array of europium(III) was obtained as an alternate mixture of the enantiomers of 13−, whereas lanthanum(III) had nine DMF ligands in its array structure. Lanthanide(III) ions whose ionic radii were less than 1.040 Å gave quite similar crystal packing, and different packing modes were observed when lanthanide(III) ions having ionic radii of more than 1.066 Å were used. The ionic radii of employed lanthanide(III) ions are a key factor for the regulation of crystal packing.

Figure 5. (a) Molecular structure of a metallosupramolecular array of 1·[Eu(dmf)8]. Free DMF molecules are omitted for clarity. A unit cell is shown by a gray line. (b) Side view of [Eu(dmf)8]3+ drawn with four adjacent 13−. Twin bowl 13− shown in blue and [Eu(dmf)8]3+ shown in yellow are in the same array, and 13− shown in pink are in the adjacent arrays. Intermolecular interactions are shown by dashed black lines.

even after the ligand exchange. This crystal structure would be well maintained with a range of metal center and ligand molecules. D



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DMF in a 2 mL screw top vial. After 5 days, 1·[Y(dmf)8] was formed as pale yellow prisms (71.8 mg, 41% isolated yield). 1·[La(dmf)9]. 111.5 mg of rac-1·(Me2NH2)3 and 53.7 mg of La(OTf)3 were dissolved in 0.5 mL of DMF in a 2 mL screw top vial without a cap, and the vial was placed inside a 20 mL screw top vial containing 5 mL of diethyl ether. After 1 day, 1·[La(dmf)8] was formed as pale yellow prisms (152.4 mg, 80% isolated yield). 1·[Y(dmf)6(pyo)2]. 5.9 mg of rac-1·(Me2NH2)3, 2.6 mg of Y(OTf)3, and 46.1 mg of PyO were dissolved in 0.5 mL of DMF in a 2 mL screw top vial without a cap, and the vial was placed inside a 20 mL screw top vial containing 5 mL of diethyl ether. After 13 h, 1· [Y(dmf)6(pyo)2] was formed as colorless prisms (6.8 mg, 76% isolated yield). Determination of Crystal Structures. 1·[Ln(dmf)8] and 1· [Y(dmf)6(pyo)2]. A crystal was exposed to a cold nitrogen gas stream at 120 or 150 K. X-ray diffraction images of the crystal were collected with a Bruker SMART APEX II CCD area detector with an Mo−Kα fine-focus sealed tube at the wavelength of 0.71073 Å. The distance between the crystal and the detector was 60 mm. Images were processed using the software package APEX II (Bruker AXS). The crystal structures were solved by direct methods using SHELXS-97 and refined by full-matrix least-squares using SHELXL-97.8 All of the non-hydrogen atoms were refined anisotropically, and the hydrogen atoms were included at their calculated positions. 1·[La(dmf)9]. A pale yellow crystal was exposed to a cold nitrogen gas stream at 100 K. X-ray diffraction images of the crystal were collected with a Rayonix MarMosaic 225 CCD area detector with synchrotron radiation at the wavelength of 0.7 Å at the BL26B2 station of SPring-8 (Hyogo, Japan). The distance between the crystal and the detector was 85 mm. Images were processed using HKL2000 software (HKL Research). Dynamic Light Scattering (DLS) Experiment. To a mixture of (+)-2·(Me2NH2)3 (9.0 mg, 5.0 μmol) and yttrium trifluoromethanesulfonate (2.7 mg, 5.0 μmol) was added DMF (0.5 mL), and the mixture was stirred at room temperature. After 5 min, methanol was added to the mixture, and the resulting white precipitate was corrected by centrifugal separation. 2·[Y(dmf)8] was obtained as a pale brown solid (12.2 mg). Dynamic light scattering experiments were performed using the commercially available instrument “Zetasizer-Nano ZS” (Malvern, Instruments Ltd., Worcestershire, U.K.) equipped with a 4 mW He− Ne laser (633 nm wavelength) at a fixed detector angle of 90°. Measurements were performed at 20 °C. For data analysis, the viscosity and refractive index of chloroform at 20 °C (0.57 mPa·s and 1.446, respectively) were used. Samples with a concentration of 2.0 mg/mL dissolved in chloroform were filtered (Millex, 0.45 μm pore size) before measurements. The measurements were performed in a square quartz cell. The autocorrelation functions of the backscattered light fluctuations were analyzed (Stokes−Einstein) using the DTS v4.20 software (Malvern), which provided the hydrodynamic diameter, polydispersity, and the size distribution.

Figure 6. (a) Side view of 1·[La(dmf)9] drawn with adjacent 13−. (b) Packing diagram of 1·[La(dmf)9] shown along the a axis. Each enantiomer of 13− is drawn in blue and pink, respectively. [La(dmf)9]3+ is shown in yellow. Intermolecular interactions are shown by dashed black lines. In order to highlight the interarray interactions in (b), unrelated molecules are drawn as gray wires. Free DMF molecules are omitted for clarity.

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ASSOCIATED CONTENT

S Supporting Information *

X-ray crystallographic analysis and DLS analysis data. Singlecrystal X-ray crystallographic information files (CIF) are available for all crystals. This material is available free of charge via the Internet at http://pubs.acs.org. Crystallography files are also available from the Cambridge Crystallographic Data Centre (CCDC) upon request (http://www.ccdc.cam.ac.uk, CCDC deposition numbers 1025760−1025766).

Figure 7. Crystal structure and selected crystal data of 1· [Y(dmf)6(pyo)2]. PyO ligands are shown in red and others, in gray. Free DMF molecules are omitted for clarity.

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EXPERIMENTAL SECTION

Materials. rac-1·(Me2NH2)33a and (+)-2·(Me2NH2)33b were prepared as previously described. All lanthanide(III) salts were purchased from Sigma-Aldrich Co. and used without further purification. Crystal Growth. 1·[Y(dmf)8]: A Typical Procedure. 111.5 mg of rac-1·(Me2NH2)3 and 53.7 mg of Y(OTf)3 were dissolved in 1.0 mL of

AUTHOR INFORMATION

Corresponding Author

*E-mail: [email protected] (H.D.). Notes

The authors declare no competing financial interest. E



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Article

ACKNOWLEDGMENTS This work was supported by the Hyogo Science and Technology Association. We thank Drs. G. Ueno and S. Baba (Japan Synchrotron Radiation Research Institute (JASRI)) for invaluable help in data collection in the X-ray analysis of 1· [La(dmf)9]. Synchrotron radiation experiment was performed at the BL26B2 station of SPring-8 with the approval of JASRI (Proposal No. 2014A1214).

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REFERENCES

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Formation of Lanthanide (III)-Containing Metallosupramolecular

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