two new 3d lanthanide coordination polymers with benzenesulfonic and adipic acids: synthesis,...

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DOI: 10.1002/zaac.200900495

Two New 3D Lanthanide Coordination Polymers with Benzenesulfonic andAdipic Acids: Synthesis, Structure and Luminescent Properties

Zhuo Wang,[a] Feng-Ying Bai,[a] Yong-Heng Xing,*[a] Yan Xie,[a] Mao-Fa Ge,[b] andShu-Yun Niu[a]

Keywords: Rare earths; Benzenesulfonic acid; Adipic acid; IR spectroscopy; Luminescence

Abstract. Two new lanthanide complexes [Sm2(ad)2.5(BSA)(H2O)2]n(1) and [Nd2(ad)2.5(BSA)(H2O)2]n (2) (H2ad = adipic acid, HBSA =benzenesulfonic acid) were synthesized hydrothermally from the reac-tion of the lanthanide ions (Ln3+) with flexible aliphatic dicarboxylateand the rigid benzene sulfonic acid and characterized by elementalanalysis, IR spectroscopy, and single-crystal X-ray diffraction. They

Introduction

The design and synthesis of lanthanide coordination poly-mers is a field of rapid growth due to their potential applica-tions in luminescent or magnetic materials, as well as in cataly-sis and gas absorption [1–5]. In regard of this aspect,considerable progress has been made on the theoretical predic-tion and network-based approaches to control the topology andarrangement of the structures to produce useful functional ma-terials [6–8]. Lanthanide atoms enable the formation of poten-tial functional materials because of the versatile coordinationproperties and chemical characteristics arising from 4f elec-trons. Lots of functional multicarboxylate acids, such asphthalic acid [9], isophthalic acid [10], terephthalic acid [11],trimesic acid [12], pyromellitic acid [13], and 1,3,5-benzenetri-acetic acid [14], pyridine carboxylic acids, etc. [15–18] havebeen used for the synthesis of lanthanide coordination poly-mers. However, the use of sulfonic acid and its derivativesas ligands is not well investigated, and only few coordinationpolymers have been reported to date [19–23]. Benzenesulfonicacid and its derivatives show interesting properties, whichmake them potentially useful ligands such as: a) –SO3H ascoordinating group, which enables various coordination modes(Scheme 1); b) an effective biological activity with high cata-lytic property for the nitration of toluene, which enabled suc-

* Prof. Dr. Y.-H. XingE-Mail: [email protected]

[a] College of Chemistry and Chemical EngineeringLiaoning Normal UniversityDalian 116029, P. R. China

[b] Institute of ChemistryChinese Academy of SciencesBeijing 100190, P. R. ChinaSupporting information for this article is available on the WWWunder http://dx.doi.org/10.1002/zaac.200900495 or from theauthor.

1570 © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim Z. Anorg. Allg. Chem. 2010, 636, 1570–1575

crystallize monoclinic in space group P21/c. Structural analyses re-vealed that the two complexes have intricate 3D net structures con-structed by the bridging adipic ligand and benzenesulfonic acid. Thethermogravimetric analysis of 1 and 2, as well as photoluminescentproperties of 1 are discussed in detail.

cessful application as catalyst for a large number of organictransformations, etc. [24]. For the flexible adipic acid, relatedcoordination polymers were reported [25, 26].So far, our group has synthesized lanthanide complexes withboth rigid and flexible polycarboxylates as mixed ligands toconstruct a new family of functional material, and a series ofthe lanthanide complexes have been reported [26–28]. In orderto investigate the influence of coordination modes of aliphaticpolycarboxylates on lanthanides and benzenesulfonic acid, inthis experiment adipic acid was introduced to the system as aflexible acid. To the best of our knowledge, the two synthe-sized complexes [Sm2(ad)2.5(BSA)(H2O)2] (1) and[Nd2(ad)2.5(BSA)(H2O)2] (2) (H2ad = adipic acid, HBSA =benzenesulfonic acid) are the first examples of lanthanide com-plexes with both benzenesulfonic and adipic acid ligands.Their thermal stability and their luminescent properties werealso investigated.

Experimental SectionMaterials and MethodsAll chemicals purchased were of reagent grade or better and were usedwithout further purification. Lanthanide chlorides were prepared bydissolving lanthanide oxides in 12 m HCl and afterwards evaporationat 100 °C until the crystal film formed. C and H analyses were per-formed with a Perkin–Elmer 240C automatic analyzer at the analysiscenter of Liaoning Normal University. Infrared (IR) spectra were re-corded with a JASCO FT/IR-480 PLUS Fourier transform spectropho-tometer from KBr pellets in the range 200–4000 cm–1. Luminescencespectra were recorded with a JASCO FP-6500 Spectrofluorimeter(solid) in the range 200–850 nm. Thermogravimetric anaylses (TGA)were performed under nitrogen at 1 atm with a heating rate of10 °C·min–1 with a Perkin–Elmer Diamond TG/DTA. X-ray powderdiffraction (XRD) data were collected with a Bruker Advance-D8 withCu-Kα radiation, in the range 5° < 2θ < 60°, with a step size of 0.02°(2θ) and an acquisition time of 2 s per step.

3D Lanthanide Coordination Polymers with Benzenesulfonic and Adipic Acids

Scheme 1. Schematic representation of the reported connection modes for metal–SO3 ligand complexes.

Synthesis of [Sm2(ad)2.5(BSA)(H2O)2] (1)

The complex was prepared by hydrothermal reaction. SmCl3·6H2O(0.20 g, 0.56 mmol), benzenesulfonic acid (HBSA, 0.15 g,1.00 mmol), adipic acid (0.14 g, 1.00 mmol), and H2O (10 mL) weremixed in 25 mL beaker. The pH value was adjusted to 4–5 with trieth-ylamine. After stirring for 2 h, the mixture was sealed in the beaker andheated at 180 °C for three days. Afterwards, the mixture was cooled to100 °C (10 °C·h–1), followed by slow cooling to room temperature.After filtration, the product was washed with distilled water and driedat room temperature. Yellow crystals suitable for X-ray diffractionanalysis were obtained in ca. 40.12 % yield based on SmIII. Elementalanalysis: C21H29O15SSm2 (Mr = 854.20 g·mol–1): calcd: C 29.53; H3.42 %; found: C 29.47; H 3.51 %. IR (KBr pellet): ν̃ = 3392, 2936,2866, 1549, 1434, 1323, 1232, 1174, 1132, 1049, 1022, 933, 733, 690,608, 560, 513, 376 cm–1.

Synthesis of [Nd2(ad)2.5(BSA)(H2O)] (2)

An identical procedure as employed in the synthesis of 1 was followedto prepare compound 2 with the exception that SmCl3·6H2O was re-placed by NdCl3·6H2O. Violet crystals of 2 were obtained. Elementalanalysis: C21H29O15SNd2 (Mr = 841.99 g·mol–1): calcd: C 29.96; H3.47 %; found: C 29.88; H 3.41 %. IR (KBr pellet): ν̃ = 3396, 2938,2866, 1548, 1435, 1323, 1233, 1175, 1132, 1049, 1022, 933, 733, 690,609, 560, 513, 377 cm–1.

Single-Crystal X-ray Diffractometry

Suitable single-crystals of both complexes were mounted on glass fi-bers for X-ray measurement. Reflection data were collected at roomtemperature with a Rigaku R-AXIS RAPID IP diffractometer withgraphite monochromatized Mo-Kα radiation (λ = 0.71073 Å). All ab-sorption corrections were performed by using the SADABS program[29]. Crystal structures were solved by direct methods. All non-hydro-gen atoms were refined anisotropically. All hydrogen atoms were fixedat calculated positions with isotropic thermal parameters. All calcula-tions were performed using the SHELX-97 program [30]. Crystal dataand details of the data collection and the structure refinement are givenin Table 1. Selected bond lengths and bond angles of complexes 1 and2 are listed in Table 2.

The atomic coordinates, isotropic thermal parameters, and completebond lengths and angles were deposited with the Cambridge Crystallo-graphic Data Center. CCDC-740795 (1) and CCDC-740796 (2) containthe supplementary crystallographic data for 1 and 2. These data canbe obtained free of charge via http://www.ccdc.cam.ac.uk/conts/re-trieving.html, or from The Cambridge Crystallographic Data Centre,12 Union Road, Cambridge CB2 1EZ, UK; Fax: +44-1223-336-033;or E-Mail:[email protected].

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Table 1. Crystallographic data for complexes 1 and 2.

Formula C21H29O15SSm2 C21H29O15SNd2M /g·mol–1 854.20 841.99Crystal system Monoclinic MonoclinicSpace group P21/c P21/ca /Å 11.971(2) 12.010(2)b /Å 15.940(3) 16.002(3)c /Å 16.398(3) 16.475(6)β /° 107.27(3) 116.89(2)V /Å3 2790.1(12) 2823.9(10)Z 4 4Dcalc 2.034 1.980Crystal size /mm 0.25 × 0.18 × 0.08 0.13 × 0.09 × 0.05F(000) 1660 1644μ(Mo-Kα) /mm–1 4.312 3.779θ /° 3.07–27.47 3.05–27.48Reflections collected 26852 25754Independent reflections6390 6371[I > 2σ(I)]Parameters 392 384Δ(ρ) /e·Å–3 0.606 and –1.106 1.483 and –2.064Goodness of fit 1.084 1.025Ra) 0.0334, (0.0315)b) 0.0884, (0.1652)b)wR2a) 0.0406, (0.0505)b) 0.1650, (0.2049)b)

a) R = Σ||Fo|–|Fc||/Σ|Fo|, wR2 = [Σ(w(Fo2–Fc2)2/[Σ(w(Fo2)2)1/2; [Fo>4σ(Fo)].b) Based on all data.

Supporting Information (see footnote on the first page of this article):Selected bond lengths and bond angles for complex 2. Powder XRDpatterns for complexes 1 and 2. Structure and coordination environ-ment of complex 2. DTA/TG curves for complex 2. FT-IR spectra forcomplexes 1 and 2.

Results and DiscussionComplexes 1 and 2 were obtained by hydrothermal methodsat 180 °C in a water system, in which triethylamine was usedas template and base to adjust the pH value. However, it wasfound that if we used ethylenediamine instead of triethylamineto adjust the pH, the same results were obtained. But whenKOH or NaOH were used instead of an organic amine, theyield and crystal quality of the complexes were not very good.This fact suggests that the organic amine might play a role inadjusting the pH and in facilitating the coordination of the sul-fonic group (–SO3) to the metal ions. In addition, when lantha-nide nitrates were used as starting material instead of lantha-nide chlorides and triethylamine was used to adjust the pH, theyield and crystal qualities of the complexes were also satisfy-ing. Therefore, the organic amine seems to play an important

Y.-H. Xing et al.ARTICLE

Table 2. Selected bond lengths /Å and bond angles /° for complex 1.

Sm1–O1 2.353(2) Sm1–O15 2.378(2) Sm1–O4 2.422(2)Sm1–O5 2.464(3) Sm1–O7 2.472(2) Sm1–O3 2.477(2)Sm1–O8 2.481(2) Sm1–O2 2.612(2) Sm1–O6 2.665(2)Sm2–O12 2.364(2) Sm2–O11 2.373(2) Sm2–O6 2.398(3)Sm2–O13 2.400(3) Sm2–O10 2.408(2) Sm2–O2#1 2.418(2)Sm2–O14 2.490(2) Sm2–O15 2.558(2)O1–Sm1–O15 155.43(9) O1–Sm1–O4 93.94(9) O15–Sm1–O4 86.37(9)O1–Sm1–O5 79.98(9) O15–Sm1–O5 77.33(9) O4–Sm1–O5 68.29(9)O1–Sm1–O7 76.83(8) O15–Sm1–O7 116.36(8) O4–Sm1–O7 143.55(9)O5–Sm1–O7 141.14(9) O1–Sm1–O3 128.20(9) O15–Sm1–O3 76.00(9)O4–Sm1–O3 78.84(9) O5–Sm1–O3 138.53(9) O7–Sm1–O3 79.76(9)O1–Sm1–O8 80.87(9) O15–Sm1–O8 81.83(9) O4–Sm1–O8 135.68(9)O5–Sm1–O8 67.46(9) O7–Sm1–O8 78.33(9) O3–Sm1–O8 137.49(8)O1–Sm1–O2 78.22(8) O15–Sm1–O2 124.46(8) O4–Sm1–O2 70.51(8)O5–Sm1–O2 131.38(8) O7–Sm1–O2 73.08(8) O3–Sm1–O2 50.81(8)O8–Sm1–O2 147.66(8) O1–Sm1–O6 122.26(8) O15–Sm1–O6 66.24(8)O4–Sm1–O6 141.60(8) O5–Sm1–O6 125.90(9) O7–Sm1–O6 50.17(8)O3–Sm1–O6 69.05(8) O8–Sm1–O6 68.89(8) O2–Sm1–O6 102.43(8)O12–Sm2–O11 89.40(9) O12–Sm2–O6 138.56(9) O11–Sm2–O6 83.68(9)O12–Sm2–O13 71.53(10) O11–Sm2–O13 99.51(12) O6–Sm2–O13 69.49(10)O12–Sm2–O10 147.14(9) O11–Sm2–O10 87.26(10) O6–Sm2–O10 73.44(9)O13–Sm2–O10 141.20(10) O12–Sm2–O2#1 73.57(8) O11–Sm2–O2#1 82.33(9)O6–Sm2–O2#1 144.63(8) O13–Sm2–O2#1 145.02(9) O10–Sm2–O2#1 73.58(9)O12–Sm2–O14 75.70(8) O11–Sm2–O14 157.53(9) O6–Sm2–O14 118.61(8)O13–Sm2–O14 91.71(11) O10–Sm2–O14 96.14(9) O2#1–Sm2–O14 77.41(8)O12–Sm2–O15 116.41(8) O11–Sm2–O15 150.60(8) O6–Sm2–O15 67.75(8)O13–Sm2–O15 77.50(10) O10–Sm2–O15 78.32(8) O2#1–Sm2–O15 117.00(8)O14–Sm2–O15 51.02(8)

Symmetry transformations used to generate equivalent atoms: #1 x+1/2, –y+1/2, z+1/2.

role in enabling the coordination of the –SO3 group to thelanthanide ions.Additionally, the compositions of complexes 1 and 2 wereconfirmed by elementary analysis and IR spectroscopy (FigureS7). The phase purities of the bulk samples were identified byX-ray powder diffraction (Figure 1 and Figure S1).

Figure 1. XRD powder patterns: a) Simulated XPRD pattern calcu-lated from the single-crystal structure of complex 1. b) ExperimentalXPRD for complex 1.

Single-crystal X-ray structure analyses revealed that com-pounds 1 and 2 are isostructural. Therefore, complex 1 is takenas an example to be discussed in detail.

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The asymmetric unit of [Sm2(ad)2.5(BSA)(H2O)2] (1) con-tains 2.5 adipate ligands, one benzenesulfonic acid ligand, twocoordinated water molecules and two samarium atoms. Thecoordination environments of Sm1 and Sm2 are shown in Fig-ure 2. Sm1 is nonacoordinated by seven oxygen atoms belong-ing to five different adipic acid ligands, the remaining two arefrom one benzenesulfonic acid molecule and one coordinatedwater molecule, respectively (Figure 2a). Eight oxygen atomsare coordinated to Sm2, six are from five different adipic acidmolecules and the remaining two are from one benzenesulfonicacid molecule and one coordinated water molecule, respec-tively (Figure 2c). The Sm1–Ocarboxylate bond lengths are in therange 2.353–2.665 Å (2.464 Å for Sm1–Owater and 2.481 Å forSm1–Osulfonic), the Sm2–Ocarboxylate bond lengths are in range2.364–2.558 Å (2.400 Å for Sm2–Owater and 2.408 Å forSm2–Osulfonic), all of them are similar to those reported forother Sm–oxygen donor complexes [26–28], however it is ap-parently that the bond lengths of Sm1–Owater and Sm1–Osulfonicare longer than those of Sm2–Owater and Sm2–Osulfonic, respec-tively. This is because of the different coordination environ-ments of the two samarium atoms.The coordination modes of adipate in both complexes areshown in Figure 3a, b. As it is obvious, it adopts two types ofcoordination modes. In the first case the carboxylate groupsare found to coordinate bridging tridentately on one end of themolecule and to coordinate bridging bidentately on the otherend of the molecule. In the other case the carboxylate groupsare found to coordinate bridging tridentately on both ends ofthe molecule. Two oxygen atoms of the benzenesulfonic acid


Figure 2. a) Coordination environment of Sm1 in complex 1. b) Distorted square antiprism coordination polyhedron of Sm1 ion. c) Coordinationenvironment of Sm2 in complex 1. d) Distorted square antiprism coordination polyhedron of Sm2 ion.(#1: x+1/2, –y+1/2, z+1/2).

ligand are coordinated to two metal atoms to form a μ2–η1-η1

mode. (shown in Figure 3c)

Figure 3. a, b) Coordination modes of the adipate ligand. c) Coordina-tion mode of the BSA ligand in complex 1.

It is necessary to explore the connection modes of the metalatoms and the organic ligands to get a better understanding ofthe framework structure. The polyhedron centers SmO9 (Fig-ure 2b) and SmO8 (Figure 2d) with the distance 4.161(69) Åbetween the two adjacent polyhedra are bridged by the SO3–

and COO– groups to form an infinite one-dimensional chainstructure (Figure 4a). These chains are further linked by adi-pate ligands, which adopt the coordination mode shown inScheme 1a, along the [010] direction to form a 2D network(Figure 4b). The 2D network is further connected by adipic


acid to form a 3D channel framework along [001] (Figure 5).Surprisingly, it was found that the 3D framework of the titlecomplexes could be constructed just by flexible aliphatic li-

Figure 4. a) One-dimensional polyhedra chain structure formed by sa-marium and its corresponding centrosymmtric atoms through the ter-minal carboxylate and sulfur bridging interactions. b) One-dimensionalchains linked to each other by adipates in [010] direction to form a 2Dnetwork.

Y.-H. Xing et al.ARTICLE

gands (Figure S2), this is in contrast to complexes reportedpreviously [26]. It is suggested that the coordination modes ofrigid and flexible polycarboxylates have some influence on thepacking of the framework, and that the action of rigid andflexible ligands in controlling the dimension of frameworkpacking is different.

Figure 5. 3D packing structure of complex 1.

Thermal Properties

The thermal stability of the complexes in air was examinedby thermogravimetric techniques in the temperature range 50–1000 °C. Figure 6 shows the TG/DTA curves for complex 1at a heating rate of 10 °C·min–1 under nitrogen. The thermaldecomposition process of complex 1 can be divided into twostages. The first weight loss of 4.99 % between 115 and198 °C corresponds to the release of two coordinated watermolecules (4.22 %, theoretical weight loss). The secondweight loss of 41.85 % is observed in the temperature range325–525 °C and is attributed to the release of two and halfadipate acid molecules (42.18 %, theoretical weight loss). Thegradually loss of benzenesulfonic acid results in a remainingmixture of Ln2O3 and carbon. For compound 2 the thermaldecomposition process shows three stages (Figure S6), the ini-tial weight loss in the range 65–111 °C corresponds to the lossof one coordinated water molecule (calcd. 2.14 %, observed1.96 %), the second weight loss in the range 125–283 °C cor-responds to the loss of one water molecule, one half adipatemolecule and one CO2 molecule (calcd. 15.88 %, observed15.05 %). The third weight loss corresponds to the loss of theremaining adipate ligands (calcd. 29.01 %, observed 29.81 %).Although the structures of the two complexes are similar, theirthermal behavior is slightly different. This might be becauseof the fact that the complexes contain different metal ions,which have an impact on the courses of thermal decomposi-tion. However, the DTA curves of the two complexes are simi-lar.

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Figure 6. TG/DTA curves of complex 1.

Photoluminescent Properties

The luminescent behavior of complex 1 was investigated insolid-state at room temperature. When excited at 530 nm, itemits a pink light at room temperature. The emission and exci-tation spectrum is shown in Figure 7, a broad and strong emis-sion band, which appeared at 270–350 nm was assigned tointraligand transition of benzenesulfonic acid, whereas theband in the region 540–640 nm was assigned to the emissionof samarium, which corresponds to the 5D5/2 → 7Fn (n = 5/2,7/2, and 9/2) transitions at 561, 576, and 595 nm, respectively.But it was found that the emission signals of samarium arevery weak. It might be because the triplet-state energy of li-gand is a little greater than the energy gap (ΔE) between theexcited state and ground state of the lanthanide metal ion, sothat efficient luminescence could be obtained [31].

Figure 7. Room-temperature solid-state photoluminescence spectra ofcomplex 1. [Excitation spectrum (λem = 561 nm); emission spectrum(λex = 530 nm)].


ConclusionsThe first two 3D lanthanide complexes with rigid and flexi-ble multicarboxylate acids, namely [Sm2(ad)2.5(BSA)(H2O)2]n(1) and [Nd2(ad)2.5(BSA)(H2O)2]n (2) were synthesized hydro-thermally. It is found that choosing the templates is a mainfactor in the reaction system because of the weak coordinationability of benzenesulfonic acid. Structural analysis shows thatthe coordinated modes of rigid and flexible polycarboxylateligands affect the packing fashion of metal-organic-frameworkof the complexes, and the function of the rigid and the flexiblepolycarboxylate ligands in different lanthanide complexes isdifferent [28].

AcknowledgementWe wish to express our sincere gratitude to National Natural ScienceFoundation of China (Grant No. 20771051) and Education Foundationof Liaoning Province in China (Grant 2007T093) for financial assist-ance.

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Received: October 19, 2009Published Online: February 11, 2010

two new 3d lanthanide coordination polymers with benzenesulfonic and adipic acids: synthesis,...

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