A New Europium Coordination Compound Supported by 4,6-Dibenzoylisophthalic Acid Ligands 1

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1 35 卷 5 期 结构化学 (JIEGOU HUAXUE) Vol. 35, No Chinese J. Struct. Chem A New Europium Coordination Compound Supported by 4,6-Dibenzoylisophthalic Acid Ligands 1 ZHU Xiao-Fei a XIE Xiao-Yan a BI Yan-Feng b2 YANG Yu a ZHOU De-Feng a a (School of Chemistry and Life Science, Changchun University of Technology, Changchun , China) b (College of Chemistry, Chemical Engineering and Environmental Engineering, Liaoning Shihua University, Fushun , China) ABSTRACT A unique metal-organic framework (MOF) [Eu 2 (L) 3 (phen) 2 ] n (1, H 2 L = 4,6-dibenzoylisophthalic acid, phen = 1,10-phenanthroline) has been synthesized under hydrothermal conditions and characterized by single-crystal X-ray analysis, elemental analyses, powder X-ray diffraction, TGA measurement as well as IR spectra. The crystal is of triclinic system, space group P1, C 90 H 52 Eu 2 N 4 O 18, M r = , a = (4), b = (6), c = (10) Å, α = (3), β = (5), γ = (3), V = (3) Å 3, Z = 2, D c = g/cm 3, F(000) = 1780, μ(mokα) = mm -1, R int = , R = and wr = for observed reflections with I > 2σ(I). X-ray analysis shows that the title compound exhibits a 2D layer structure linked by L ligands with two coordination modes and two distinguished conformations, and further linked into a 3D supramolecular architecture through C H O weak interactions between hydrogen of phen phenyl ring and the carboxylate oxygen atom of adjacent sheets. In addition, the luminescence property of 1 was investigated. Keywords: 4,6-dibenzoylisophthalic acid, europium, coordination modes, hydrothermal; DOI: /j.cnki INTRODUCTION Metal-organic frameworks (MOFs) are promising multifunctional luminescent materials largely due to the presence of metal ions or clusters and organic linkers, providing a wealth of opportunities for engineering applications [1-5]. A lot of work has been concentrated on the designing and synthesizing of MOFs with lanthanide-organic framework for aromatic ligands. MOFs are very famous as they are excellent in sensitizing the lanthanide luminescence by well-known antenna effect in which the ligands are first excited, followed by energy transfer from the ligand s singlet excited states to their triplet excited states (i.e. intersystem crossing), and then to the emissive states of the lanthanide ion [6-10]. One particularly rich family of coordination polymer utilizes bridging carboxylate ligands, such as 1,3/1,4-benzenedicarboxylate [11-15] as well as modified 1,3/1,4-benzenedicarboxylate [16-21], frequently producing polymeric structures of various dimensionalities. The structural sophistication can be further enhanced through the use of ancillary ligands. 4,6-Dibenzoylisophthalic acid (H 2 L), a ligand Received 10 August 2015; accepted 19 November 2015 (CCDC ) 1 This project was supported by the NNSFC (No ), and Xiaonei Foundation of Changchun University of Technology 2 Corresponding author. Born in 1979, professor, majoring in functional coordination chemistry. biyanfeng@lnpu.edu.cn

2 2016 Vol. 35 结构化学 (JIEGOU HUAXUE)Chinese J. Struct. Chem. 759 benzoyl substituted 1,3-benzenedicarboxylate, has been recently reported by Zhang and coworkers [22-32]. Meanwhile, H 2 L as an excellent ligand in the self-assembly of coordination polymers can slightly change the dihedral angle of benzoyl to meet the requirements of coordination and the benzoyl can form C/O H π and π π weak interactions as steering forces on the control of molecular selfassembly. Prompted by these somewhat contradictory findings and seeking possible structural variations and property changes in analogous coordination compounds, herein we report the syntheses and characterization of a new lanthanide compound [Eu 2 (L) 3 (phen) 2 ] n (1, phen = 1,10-phenanthroline), which exhibits a 2D layered structure, and the adjacent 2D sheets of 1 are further linked into a 3D network by weak C H O hydrogen bonding interactions. Two coordination modes of L ligands were observed in 1 and two conformations of L (cis- and trans-) were defined, in which cis-isomer was firstly observed in lanthanide compounds. The fluorescent property and thermal stability of compound 1 have been investigated. 2 EXPERIMENTAL 2. 1 Materials and physical measurements H 2 L was synthesized according to the literature [33] and the other chemicals were purchased commercially and used as received without further purification. The FI-IR spectra were recorded using KBr pellets in the range of 4000~400 cm 1 on a Mattson Alpha-Centauri spectrometer. Elemental analyses for C, H and N were performed on a Perkin-Elmer 2400 Elemental Analyzer. Powder X-ray diffraction (PXRD) patterns were collected on a Rigaku D max 2000 X-ray diffractometer with graphite-monochromatized Cu-Kα radiation (λ = nm) and 2θ ranging from 5 to 50 with a step size of Thermogravimetric analyses (TGA) were performed on a Perkin-Elmer Thermal Ana- lyzer under a N 2 atmosphere with the sample heated in an Al 2 O 3 crucible at a heating rate of 5 K min 1. The properties and lifetime were measured on a FLS920 Edinburgh Luminescence Spectrometer Synthesis of [Eu 2 (L) 3 (phen) 2 ] n (1) Eu(NO 3 ) 3 6H 2 O (44.6 mg, 0.1 mmol), H 2 L (56.10 mg, 0.15 mmol) and phen (19.8 mg, 0.1 mmol) were mixed in 15 ml of H 2 O and the ph was adjusted to about 5.5 with 0.1 M NaOH. Then it was sealed in a 25 ml Teflon-lined reactor and heated at 160 C for 72 h. After that the reaction system was cooled to room temperature at a rate of 3 C h 1 to generate colorless block crystals (~63% yield based on Eu(III)). Anal. Calcd. for C 90 H 52 Eu 2 N 4 O 18 ( ): C, 60.68; H, 2.94; N, Found: C, 60.61; H, 2.98; N, IR (KBr, cm 1 ): 3443 (m), 3068(w), 1673 (s), 1658 (s), 1569 (m), 1483 (m), 1389 (s), 1315 (s), 1176 (w), 1138 (w), 1104 (w), 921 (w), 892 (w), 807 (w), 720 (m), 620 (m), 426 (w) Structure determination Single crystals were glued onto a fiberglass for X-ray diffraction data collection. Data sets of 1 with approximate dimensions of 0.32mm 0.30mm 0.30mm was collected on a Bruker Smart Apex CCD diffractometer, using a graphite-monochromated Mo-Ka radiation (λ = Å) at 293 K. Absorption correction of 1 was applied by using the SADABS. The structure was solved by direct methods followed by difference Fourier method and refined by full-matrix least-squares on F 2 using the SHELXS-97 package [34]. A total of reflections were collected in the range of 2.83 θ 26.00, of which were unique (R int = ) and were observed with I > 2σ(I). All non-hydrogen atoms were refined anisotropically, and all hydrogen atoms on organic ligands were placed in the geometrically idealized positions using a riding model. The final R = 0.026, wr = (w = 1/[σ 2 (F 2 o ) + (0.0245P) P], where P = 2 (F o + 2F 2 c )/3), S = 1.057, (Δρ) max = 0.655, (Δρ) min = e/å 3 and (Δ/σ) max = The selected bond lengths and bond angles are listed in Table 1.

3 ZHU X. F. et al.: A New Europium Coordination Compound 760 Supported by 4,6-Dibenzoylisophthalic Acid Ligands No. 5 Table 1. Selected Bond Lengths (Å) and Bond Angles ( ) Bond Dist. Bond Dist. Bond Dist. Eu(1) O(4) (18) Eu(1) N(2) 2.534(2) Eu(2) O(14) (18) Eu(1) O(3) (18) Eu(1) N(1) 2.548(2) Eu(2) O(9) 2.525(2) Eu(1) O(1) (19) Eu(2) O(15) 2.295(2) Eu(2) N(4) 2.512(2) Eu(1) O(2) (19) Eu(2) O(16) (18) Eu(2) N(3) 2.596(2) Eu(1) O(8) 2.452(2) Eu(2) O(10) 2.396(2) Eu(1) O(7) 2.495(2) Eu(2) O(13) (19) Angle ( ) Angle ( ) Angle ( ) O(4) Eu(1) O(3) 80.66(7) O(8) Eu(1) N(2) (8) O(15) Eu(2) N(4) (7) O(4) Eu(1) O(1) 83.52(7) O(7) Eu(1) N(2) 74.70(7) O(16) Eu(2) N(4) 73.97(7) O(3) Eu(1) O(1) (7) O(4) Eu(1) N(1) 84.56(7) O(10) Eu(2) N(4) 82.06(8) O(4) Eu(1) O(2) (7) O(3) Eu(1) N(1) 71.61(7) O(13) Eu(2) N(4) (7) O(3) Eu(1) O(2) 85.36(6) O(1) Eu(1) N(1) (7) O(14) Eu(2) N(4) 91.62(7) O(1) Eu(1) O(2) 53.49(6) O(2) Eu(1) N(1) (7) O(15) Eu(2) O(9) (7) O(4) Eu(1) O(8) 8.84(8) O(8) Eu(1) N(1) 76.90(7) O(16) Eu(2) O(9) (7) O(3) Eu(1) O(8) (7) O(7) Eu(1) N(1) (8) O(10) Eu(2) O(9) 52.69(7) O(1) Eu(1) O(8) 93.54(7) N(2) Eu(1) N(1) 64.49(8) O(13) Eu(2) O(9) 78.48(7) O(2) Eu(1) O(8) (7) O(15) Eu(2) O(16) 89.28(7) O(14) Eu(2) O(9) 75.43(7) O(4) Eu(1) O(7) (7) O(15) Eu(2) O(10) 94.72(8) N(4) Eu(2) O(9) 71.60(7) O(3) Eu(1) O(7) (6) O(16) Eu(2) O(10) (7) O(15) Eu(2) N(3) 81.55(7) O(1) Eu(1) O(7) 78.54(8) O(15) Eu(2) O(13) 75.58(7) O(16) Eu(2) N(3) 71.94(7) O(2) Eu(1) O(7) 83.23(7) O(16) Eu(2) O(13) (7) O(10) Eu(2) N(3) 71.68(7) O(8) Eu(1) O(7) 52.28(7) O(10) Eu(2) O(13) (8) O(13) Eu(2) N(3) (7) O(4) Eu(1) N(2) (7) O(15) Eu(2) O(14) (7) O(14) Eu(2) N(3) (7) O(3) Eu(1) N(2) 79.16(7) O(16) Eu(2) O(14) 82.81(6) N(4) Eu(2) N(3) 64.71(8) O(1) Eu(1) N(2) (7) O(10) Eu(2) O(14) (7) O(9) Eu(2) N(3) (7) O(2) Eu(1) N(2) 80.11(7) O(13) Eu(2) O(14) 53.21(6) 3 RESULTS AND DISCUSSION 3. 1 Structure description of [Eu 2 (L) 3 (phen) 2 ] n (1) According to the single-crystal X-ray diffraction and Powder X-ray diffraction, compound 1 crystallizes in triclinic space group P1. The asymmetric unit of 1 consists of two crystallographically independent Eu(III) ions (Eu(1) and Eu(2)), three L anions and two phen ligands. As shown in Fig. 1a, the Eu1(III) center is octa-coordinated by six carboxylate oxygen atoms (O(1), O(2), O(3), O(4), O(7), O(8)) from μ 3 -(η 1 :η 1 )-(η 1 :η 1 ) (Scheme 1a), μ 2 -(η 1 :η 1 )-(η 1 :η 1 ) (Scheme 1b) L ligands, and two nitrogen atoms (N(1) and N(2)) from one phen to form a distorted dodecahedral geometry (Fig. 1b). The coordination mode of Eu(2) atom is similar as that of Eu(1), coordinating with two oxygen atoms (O(9), O(10)) from μ 2 -(η 1 :η 1 )-(η 1 :η 1 ) (Scheme 1b) L ligands, four oxygen atoms (O(13), O(14), O(15), O(16)) from μ 3 -(η 1 :η 1 )-(η 1 :η 1 ) (Scheme 1c) L ligand and two nitrogen atoms N(3) and N(4) from one phen. The Eu O bond lengths range from (18) to 2.525(2) Å (average Å), and the Eu N bond lengths are 2.512(2) to 2.596(2) Å (average Å), which are comparable to those for the early reported Eu(III) compounds involving benzenedicarboxylate ligands (Table 1) [30]. Herein, L ligand in 1 adopts two configurations, cis-(scheme 1a) and trans- (Scheme 1b, c) considering direction of two benzoyl rings to the isophthalate ring. Two μ 2 -(η 1 :η 1 ) bridging carboxyl groups form two L ligands adopting dimonodentate coordination fashions to link two neighboring Eu atoms (Eu(1) and Eu(1), Eu(2) and Eu(2)) into a dinuclear lanthanide SBU [Eu 2 O 4 (CO 2 ) 6 ] with the Eu Eu distances of (4) Å (Fig. 2a) and (3) Å (Fig. 2b), respectively. This kind of loop-like individual binuclear unit employs chelate carboxylate groups coordination (Scheme1b) to afford a 1D chain (Fig. 2c). And then the 1D chains are further linked into a 2D layer structure by the

4 2016 Vol. 35 结构化学 (JIEGOU HUAXUE)Chinese J. Struct. Chem. 761 two ligands of L (Scheme 1 a, c) with a 4 4 network (Fig. 3a). Thanks to these bulky benzoyl groups, the adjacent 2D sheets of 1 are further linked into a 3D supramolecular architecture through C(68) H(68) O(18) interactions between the hydrogen of phen phenyl ring and the carbonyl oxygen atom (Fig. 3b) (C(68) H(68), 0.93 Å, H(68) O(18), 2.40 Å, C(68) H(68) O(18), 3.275(4) Å, (C(68)H(68)O(18)), 157, symmetry code: 1 x,1 y, 1 z). Meanwhile, the weak hydrogen bonds should also be helpful to guide and stabilize the 3D supra- molecular architecture of 1. Scheme 1. Two coordination modes (a b) of L with two configurations cis-(a) and trans-(b, c) Fig. 1. (a) Coordination environment of the Eu(III) in 1 (Symmetry codes: #1: x+2, y+1, z; #3: x+1, y, z; #4: x, y, z+1; #5: x+1, y, z+1). (b) Distorted dodecahedral geometry of Eu(III) Fig. 2. Two L ligands linking two neighboring Eu atoms into a dinuclear lanthanide SBU [Eu 2 O 4 (CO 2 ) 6 ] (Eu1-Eu1, a and Eu2-Eu2, b), respectively. (c) A 1D chain linked by μ 2 -(η 1 :η 1 )-(η 1 :η 1 ) L ligands

5 ZHU X. F. et al.: A New Europium Coordination Compound 762 Supported by 4,6-Dibenzoylisophthalic Acid Ligands No. 5 Fig. 3. (a) 2D layer of 1. (b) 3D supramolecular framework constructed via the interlayer C(68) H(68) O(18) hydrogen bonds The dihedral angles between the two benzoyl rings in 1 are (Scheme 1a), (Scheme 1b) and (Scheme 1c), respectively. While the two benzoyl rings in other lanthanide compounds reported are , and [23]. It is clear that steric hindrance plays an important role in the whole framework. And the benzoyl, aromatic substituent, may indeed rotate around the central phenyl ring. As far as we know, it is the first example that lanthanide clusters with cisconformations of L, worked as 4-connected nodes in the coordination polymers based on 4,6-dibenzoylisophthalic acid and its derivatives. This flexibility should be promising in assembling interesting structures XRD patterns and thermal analysis The synthesized product of compound 1 has been characterized by powder X-ray diffraction (PXRD) (Fig. 4). The experimental PXRD patterns correspond well with the result simulated from the singlecrystal data, indicating high purity of the synthesized sample. The thermal stability of compound 1 was carried out from room temperature to 800 C under a nitrogen atmosphere at a heating rate of 5 C min 1. As shown in Fig. 5, The TGA curve suggests that 1 is stable up to 340 C, and the organic groups start to decompose gradually and exhibit continuous weight loss. No obvious thermally stable stages are observed and the framework structure begins to collapse. Fig. 4. Measured and calculated powder Fig. 5. TGA curves of compound 1 X-ray diffraction (PXRD) pattern of Photoluminescence properties The solid-state luminescence of compound 1 was investigated at room temperature (Fig. 6). Upon excitation at 350 nm, compound 1 exhibits four emission bands at 579, 591, 613, 651 and 696 nm, mainly originating from 5 D 0 7 F J (J = 0, 1, 2, 3, 4) transitions of characteristic of Eu(III) ion, respectively [35-37]. It is indicated that the 4,6-dibenzoyliso-

6 2016 Vol. 35 结构化学 (JIEGOU HUAXUE)Chinese J. Struct. Chem. 763 phthalic acid ligand process efficient energy transfer to Eu 3+ ion. The quite weak emission 5 D 0 7 F 0 at 579 nm is attributed to the symmetry-forbidden emission of the Eu 3+ ions in 1. The moderately strong emission at 591 nm ( 5 D 0 7 F 1 ), which is almost unaffected by the coordination environment, may be assigned to the prominent magnetic dipole transition. It also can be seen that the intensity of 5 D 0 7 F 2 is much stronger than that of 5 D 0 7 F 1, indicating the Eu(III) ions locate in lower symmetric coordination environments in accordance with the single crystal analysis. Additionally, the emission peaks in 5 D 0 7 F 2 transition region generate splitting of the energy, which can be ascribed to the Eu(III) centers in asymmetric sites in the compound. 4 CONCLUSION In summary, a luminescent Eu coordination polymer [Eu 2 (L) 3 (phen) 2 ] n (1, H 2 L = 4,6-dibenzoylisophthalic acid, phen = 1,10-phenanthroline) has been hydrothermally synthesized and characterized. Compound 1 displays a 2D layer structure building through L ligands bridging 1D loop-like chains. The 2D layers further afford a 3D supramolecular architecture linked by C H O hydrogen bonds. Two coordination modes of 4,6-dibenzoyliso- phthalic acid with two distinguished conformations were found, revealing that the introduction of bulky steric hindrance of benzoyl can affect the structure of the coordination polymer. REFERENCES (1) Tian, R. J.; Wang, F. X.; Du, C. Y.; Feng, L. J.; Liu, Y.; Zhang, C. L.; Pan, Q. H. Template-directed synthesis of three metal oxalates via 4-connected building units. Chem. Res. Chin. Univ. 2014, 30, (2) Rocha, J.; Carlos, L. D.; Paz, F. A. A.; Ananias, D. Luminescent multifunctional lanthanides-based metal-organic frameworks. Chem. Soc. Rev. 2011, 40, (3) Chen, B.; Xiang, S.; Qian, G. Metal-organic frameworks with functional pores for recognition of small molecules. Acc. Chem. Res. 2010, 43, (4) Cui, Y.; Yue, Y.; Qian, G.; Chen, B. Luminescent functional metal-organic frameworks. Chem. Rev. 2012, 112, (5) Ji, B. M.; Deng, D. S.; Wang, W. Z.; Wang, K.; He, M. L. Structural study on four co-crystals of N-containing heteroaromatics with iodofluorobenzene. Chem. Res. Chin. Univ. 2015, 31, (6) Allendorf, M. D.; Bauer, C. A.; Bhakta, R. K.; Houk, R. J. T. Luminescent metal-organic frameworks. Chem. Soc. Rev. 2009, 38, (7) Bunzli, J. C. G.; Piguet, C. Taking advantage of luminescent lanthanide ions. Chem. Soc. Rev. 2005, 34, (8) Yang, C.; Fu, L. M.; Wang, Y.; Zhang, J. P.; Wong, W. T.; Ai, X. C.; Qiao, Y. F.; Zou, B. S.; Gui, L. L. A highly luminescent europium complex showing visible-light-sensitized red emission: direct observation of the singlet pathway. Angew. Chem., Int. Ed. 2004, 43, (9) Klink, S. I.; Hebbink, G. A.; Grave, L.; Oude Alink, P. G. B.; van Veggel, F. C. J. M.; Werts, M. H. V. Synergistic complexation of Eu 3+ by a polydentate ligand and a bidentate antenna to obtain ternary complexes with high luminescence quantum yields. J. Phys. Chem. A 2002, 106, (10) Wang, L. F.; Kang, L. C.; Zhang, W. W.; Wang, F. M.; Ren, X. M.; Meng, Q. J. New europium coordination polymers with efficient energy transfer from conjugated tetracarboxylate ligands to Eu 3+ ion: syntheses, structures, luminescence and magnetic properties. Dalton Trans. 2011, 40, (11) He, H.; Yuan, D.; Ma, H.; Sun, D.; Zhang, G.; Zhou, H. C. Control over interpenetration in lanthanide-organic frameworks: synthetic strategy and gas-adsorption properties. Inorg. Chem. 2010, 49, (12) Tao, J.; Tong, M. L.; Chen, X. M. Hydrothermal synthesis and crystal structures of three-dimensional co-ordination frameworks constructed with mixed terephthalate (tp) and 4,4 -bipyridine (4,4 -bipy) ligands: [M(tp)(4,4 -bipy)] (M = Co II, Cd II or Zn II ). J. Chem. Soc., Dalton Trans. 2000, 36, (13) Guo, X.; Zhu, G.; Sun, F.; Li, Z.; Zhao, X.; Li, X.; Wang, H.; Qiu, S. Synthesis, structure, and luminescent properties of microporous lanthanide metal-organic frameworks with inorganic rod-shaped building units. Inorg. Chem. 2006, 45, (14) Zhou, Y.; Yan, B. Imparting tunable and white-light luminescence to a nanosized metal-organic framework by controlled encapsulation of lanthanide cations. Inorg. Chem. 2014, 53, (15) Gu, X.; Xue, D. Selected controlled synthesis of three-dimensional 4d-4f heterometallic coordination frameworks by lanthanide carboxylate subunits and silver centers. Cryst. Growth Des. 2006, 6,

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