Two Unique Entangling CdII-Coordination Frameworks Constructed

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Two Unique Entangling CdII-Coordination Frameworks Constructed by Square Cd4-Building Blocks and Auxiliary N,N′-Donor Ligands Dong-Sheng Li,*,† Peng Zhang,† Jun Zhao,† Zi-Fan Fang,† Miao Du,*,‡ Kun Zou,† and Yi-Qiang Mu† †

College of Mechanical & Material Engineering, Research Institute of Materials, China Three Gorges University, Yichang 443002, China ‡ College of Chemistry, Tianjin Key Laboratory of Structure and Performance for Functional Molecule, Tianjin Normal University, Tianjin 300387, China S Supporting Information *

ABSTRACT: This work presents two unique entangled coordination polymers based on square Cd4-building blocks. Complex 1 represents the first example of 2D→ 3D parallel polycatenated architecture constructed from a 4·82-fes net, whereas complex 2 shows an unusual (3,4)-connected selfcatenated network that can be viewed as the cross-linking of a 2D + 2D→3D inclined polycatenation.

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found as the potential bis(bidentate) candidates for building molecular M4-square units, especially for assembling novel MOFs based on such square tectons.6 Among them, by incorporating the octahedral metals (CoII, NiII, or CuII), such heterocyclic dicarboxylates will take μ2-bis(bidentate)/μ3-bis (bidentate) and bridging coordination fashions, resulting in 0D molecular M4-squares and 1D or 2D M4-based coordination networks.6 Interestingly, in these 0D/1D/2D complexes, some coordination sites of metal ions are normally occupied by water ligands, and in principle, these structures can be extended to higher dimensional networks by replacing the water ligands with N-donor bridging ligands. Thus, an attractive idea is whether new types of MOFs can be constructed from such square planar M4-building blocks, and if so, what would they be like? Recently, there have been increased efforts on entangled MOFs constructed from polycarboxylates and flexible N-donor coligands.7 As a result, numerous entangled nets, such as interpenetrating, (poly)catenanes, (poly)rotaxanes, polythreading, polyknotting, self-catenated and molecular braids, etc., have been reported.8 The results will significantly enrich our knowledge of assembly processes of these supramolecular architectures. Following this strategy, we have also made a systematic investigation of entangling MOFs with mixed ligands.9 In view of the above experience, herein, we choose a rigid imidozoledicarboxylate tecton H3EtIDC to assemble

n chemistry and material science today, the interests in crystalline solids with designed structures and predictable properties continue to motivate research in metal−organic frameworks (MOFs).1,2 In this context, there has been great progress toward design, due largely to the ability to target specific molecular building blocks with given geometry and directionality (e.g., square and tetrahedron), prior to the assembled process.3 One of the most representative examples, likely owing to its reliability to form with a large range of metals, is the square M2(O2CR)4A2 paddlewheel building block (A = axial or apical sites). In fact, it has successfully been used for the design and synthesis of desired MOFs based on the network topologies where, for example, the MOF layer is composed of M2(O2CR)4A2 dimeric subunits bridged by dicarboxylate organic ligands.4 Compared with the square paddlewheel unit, other square planar building blocks, such as single metal ions with quadrangular geometries (M4-unit), have rarely been found to construct higher-dimensional MOFs, until now. It is recognized that, by combining two different precursor tectons named the angular unit and the linear unit, the former with a proper angle and the latter with two symmetrical coordinating sites, a variety of molecular squares have been achieved.5 A Cambridge Structural Database (CSD) search indicates that the majority of them are constructed by PtII or PdII ions in the square planar configuration and linear ditopic linkers.5 However, the assembly of molecular squares from bis(bidentate) linkers is rare. On the other hand, more recently, imidazole-4,5-dicarboxylic acid6a−c and its derivative 2-ethyl1H-imidazole-4,5-dicarboxlylic acid (H3EtIDC)6d,e have been © 2012 American Chemical Society

Received: January 10, 2012 Revised: February 11, 2012 Published: February 27, 2012 1697

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Figure 1. Crystal structure of 1. (a) Coordination environment of CdII. (b) The [Cd4(HEtIDC)4]4+ square unit (symmetry codes: #1 = −x + 1/2, y + 1 /2, −z + 1/2; #2 = x − 1/2, −y + 1/2, −z + 1/2; #3 = −x + 2, −y, z. (c) 2D helical layer constructed from the interweaving of right-handed and lefthanded helical chains by sharing the Cd4-squares. (d) 4.82-fes topological net.

Figure 2. Entangling framework of 1. (a) Schematic representation of the 2D → 3D parallel polycatenate architecture based on a 4.82-fes network viewed along [010] (above) and [001] (below). (b) The parallel polycatenate motif (DOC = 8).

with CdII for the in situ formation of premeditated square planar M4-building blocks, and different auxiliary N-donor spacers are introduced to tune the final network structures. Fortunately, two unique entangled coordination networks based on the square building blocks [Cd4(HEtIDC)4] were obtained. Notably, [Cd(HEtIDC)(bix)0.5(H2O)]n (1) has the first 2D → 3D parallel polycatenation pattern based on 4.82-fes networks (bix =1,4-bis(imidazol-1-ylmethyl)benzene), whereas [Cd2(HEtIDC)2(dpe)(H2O)]n (2) displays a new (3,4)connected self-catenated framework (dpe =1,2-di(4- pyridyl)ethylene).

Complexes 1 and 2 were prepared by hydrothermal reaction of Cd(NO3)2·6H2O, H3EtIDC, bix or dpe, and NaOH,10 which were fully characterized by IR, elemental analysis, PXRD, and TGA techniques. Single crystal X-ray analysis11 reveals that the asymmetric unit of 1 has one CdII ion, one HEtIDC2− anion, half a bix molecule, and one water ligand. Each CdII center is coordinated by three nitrogen and three oxygen donors from two HEtIDC2−, one bix, and one water ligands to constitute the [CdN3O3] distorted octahedral geometry (see Figure 1a). The Cd−O/N bond lengths of 2.278(4)−2.671(4) Å are within the normal range,6d,e and the bond angles around CdII range from 1698

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Figure 3. Crystal structure of 2. (a and b) Coordination environments of Cd1 and Cd2. (c) The [Cd4(HEtIDC)4]4+ square unit (symmetry codes: #1 = −x + 2, y − 1/2, −z + 3/2; #2 = −x + 1, −y + 1, −z + 1; #3 = x + 1/2, −y + 1/2, −z + 1. (d) The 3D network constructed from the 2D layers and dpe pillars. (e) (3,4)-connected topological network with the point symbol (6·8·10)2(6·83·102) (yellow for 4-connected Cd2 node, green for 3connectd Cd1 node, and purple for 3-connected μ3-HEtIDC2− node).

imidazolylphenyl)amine).14e In this case, each Cd2(Tipa)2 loop of an independent layer is penetrated by two armed rods of Tipa ligands from two adjacent layers in a parallel fashion. Therefore, complex 1 not only provides a remarkable new structural motif but also represents the first example of a 2D → 3D parallel polycatenate architecture based on 4.82-fes nets. When the conformationally flexible bix ligand is replaced with the rigid dpe building block, a rare 3D (3,4)-connected self-catenated network is afforded in the crystal structure of 2. The asymmetric unit consists of two independent CdII centers, two HEtIDC2− anions, one dpe linker, and one water ligand. The Cd1 ion is six-coordinated by three oxygen and three nitrogen atoms from three HEtIDC2− anions (see Figure 3a), while Cd2 is also six-coordinated but by one nitrogen and three oxygen atoms from two HEtIDC2− and one water ligands, plus two nitrogen atoms from two dpe linkers (see Figure 3b and Supporting Information Table S1). The Cd−O/N distances range from 2.288(3) to 2.455(3) Å, which are similar to those found in 1. In 2, two pairs of different HEtIDC2− anions (μ2κN,O:κN′,O′ and μ3-κN,O:κO:κN′,O′) bridge four CdII centers in N,O-chelating, N′,O′-chelating, and O-bridging modes to construct a symmetric molecular square [Cd4(HEtIDC)4] (see Figure 3c). The four CdII ions are located in the same plane (the mean deviation from the plane being zero), in which the adjacent Cd···Cd distances are 6.054 Å and 6.669 Å as well as the vertex angles are 93.969(5)° for Cd1···Cd2···Cd1 and 86.031(5)° for Cd2···Cd1···Cd2. Further, the μ3-HEtIDC2− anions connect the Cd1 ions in N′,O′-chelating fashion, extending the Cd4-squares into a 2D network (see Figure 3d). The adjacent layers are expanded by the rigid dpe pillars in inclining fashion to construct a binodal (3,4)-connected selfcatenated network with the point symbol of (6·8·10)2(6·83·102) (see Figure 3d and e), in which both μ3-HEtIDC2− and Cd1 serve as the 3-connected nodes, and each Cd2 is a 4-connected node. Of further interest, this self-catenated network can be viewed as the cross-linking of a 2D + 2D→3D inclined polycatenate pattern. In this case, the rigid dpe ligands link the Cd4-squares

71.48(11) to 165.27(11)° (see Table S1 of the Supporting Information). In 1, four doubly deprotonated HEtIDC2− anions adopting the bis-N,O-chelating mode (μ2-κN,O:κN′,O′) connect four CdII ions to afford a [Cd4(HEtIDC)4] molecular square unit (see Figure 1b), where the adjacent and diagonal Cd···Cd distances are 6.834 Å and 9.502 Å, respectively, and the vertex angle is 88.09(8)° for Cd···Cd···Cd, revealing a slight deviation from the ideal square geometry. Moreover, the bix ligands with cis-conformation extend these Cd4-squares to form the righthanded and left-handed helical chains, running along the [010] and [100] directions, respectively (see Figure S1 of the Supporting Information), with the same pitch of 18.795 Å. Different helical chains are interlinked by sharing the Cd4squares to result in a meso-helical layer (see Figure 1c). Notably, within such a 2D network, all Cd4-squares are almost coplanar, and the arched cis-bix ligands protrude from both sides of the layer along [100] and [010], which paves the way for entanglement (see Figure S2). Topologically, both μ2HEtIDC2− and bix ligands serve as the 2-connected spacers, and each CdII ion is 3-connected. Thus, the overall 2D network shows a uniform 3-connected 4.82-fes topology (see Figure 1d). As a result, a rather rare example of the 2D → 3D parallel polycatenation architecture is observed (see Figure 2a and Supporting Information Figure S3), where each 8-member loop of the 2D net, with two right-handed cis-bix linkers along [010] (in below adjacent net) and two left-handed cis-bix linkers along [100] (in above adjacent net), simultaneously threads through eight 8-member loops of two adjacent 2D networks (degree of catenation (DOC) = 8; see Figure 2b). So far, quite a few examples for 2D → 3D polycatenation networks in inclined fashion have been reported, whereas 2D → 3D parallel polycatenation ones are rarely known.8b,c,12 Among all parallel polycatenation frameworks, most examples are based on 63-hcb and 44-sql nets,7b,c,13 in which the degree of catenation is generally 2 or 4. Moreover, the interpenetrated 4.82-fes nets have not been well-characterized yet,14 and in this regard, only one fascinating example of 2D → 3D parallel polyrotaxane has been observed in {[Cd(Tipa)Cl2]·1.07H2O}n (Tipa = tri(41699

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Figure 4. Entangling framework of 2. (a) 2D layer constructed by the rigid dpe ligands and Cd4-squares. (b) Two sets of 2D layers in a parallel− parallel arrangement. (c) Schematic representation of the 2D + 2D → 3D inclined polycatenate framework. (d) The inclined polycatenate pattern (above, DOC = 4) and the self-catenated motif (below).

a promising route in the design and construction of fascinating MOFs based on square planar M4-building blocks. The X-ray powder diffraction (XRPD) patterns of 1 and 2 reveal that the peak positions of simulated and experimental patterns are in good agreement, demonstrating the phase purity of the products (see Supporting Information Figure S6). The difference in intensity may be owing to the preferred orientation of the crystalline powder samples. The TGA curves of 1 and 2 (see Figure S7) suggest that the loss of coordinated aqua molecules occurs in ca. 180−215 °C (found: 4.66% and calcd: 4.16% for 1; found: 2.46% and calcd: 2.28% for 2), prior to decomposition of the host frameworks, which are observed at ca. 270 and 325 °C for 1 and 2. The emission spectra of the crystalline samples exhibit the intense emissions at 462 nm for 1 and 449 nm for 2 in the blue region (λex = 320 nm), which is slightly blue-shifted (5 and 18 nm) compared with that of the free H3EtDIC ligand (λem = 444 nm with λex = 365 nm) (see Figure S8). Thus, the emission peaks of 1 and 2 may be assigned to the intraligand fluorescent emissions,16 and their difference may be a result of the effect of organic ligands coordinated to CdII and interchromophore coupling.16b,c In summary, this work presents two unusual entangled coordination networks, showing 2D → 3D parallel polycatenation or the cross-linking of 2D + 2D →3D inclined polycatenation, respectively, assembling from Cd4-square secondary building units and different N-donor coligands. These results further enrich our knowledge of structural topologies and also open up new perspectives to design entangling networks based on square planar building blocks.

to give a quasi-planar 2D layer (see Figure 4a). Packing analysis reveals two sets of such layers oriented toward different directions, with an angle of 71.75° (see Figure S4). These two sets of layers catenate to each other in a parallel−parallel (p−p) arrangement to form a 2D + 2D → 3D inclined polycatenation architecture (see Figure 4b, c, and d). Furthermore, through the linking of μ3-HEtIDC2− anions in N′,O′-chelating mode (O4 and N1, see Figure S5), a novel (3,4)-connected self-catenated network is formed (see Figure 3e), in which the 8-membered shortest circuit is catenated by two 10-membered circuits within the same network (see Figure 4d). In fact, only limited (3,4)-connected self-catenated networks have been known,15 and complex 2 represents the first example for such an architecture based on the cross-linking of 2D + 2D → 3D inclined polycatenate motifs. Significantly, similar Cd4-squares subunits, both involving four HEtIDC2− anions (four μ2-κN,O:κN′,O′ for 1, two μ2κN,O:κN′,O′ and two μ3-κN,O:κO:κN′,O′ for 2; see Supporting Information Figure S5) and four octahedral coordination Cd2+ ions, are observed in 1 and 2, which are extended by conformationally flexible bix and rigid dpe tectons to afford a 4.82-fes meso-helical layer for 1 and a quasi-planar 2D network for 2. The former possesses arched cis-bix spacers that provide a chance for interpenetration, leading to a unique 2D → 3D parallel polycatenate network, whereas the latter is oriented toward two different directions to result in a 2D + 2D → 3D inclined polycatenate net, which is joined by μ3-HEtIDC2− to form a unique (3,4)-connected self-catenated structure. In this sense, the significance of 1 and 2 will rest with not only the presence of two new entangled examples but also the supply of 1700

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S.; Batten, S. R. Angew. Chem., Int. Ed. 2004, 43, 192. (c) Batten, S. R.; Robson, R. Angew. Chem., Int. Ed. 1998, 37, 1460. (d) Batten, S. R. CrystEngComm 2001, 3, 67. (e) Carlucci, L.; Ciani, G.; Proserpio, D. M.; Rizzato, S. CrystEngComm 2002, 4, 121. (f) Wang, X.-L.; Qin, C.; Wang, E. B.; Su, Z.-M.; Li, Y. G.; Xu, L. Angew. Chem., Int. Ed. 2006, 45, 7411. (8) (a) Proserpio, D. M. Nat. Chem. 2010, 2, 435. (b) Alexandrov, E. V.; Blatov, V. A.; Kochetkov, A. V.; Proserpio, D. M. CrystEngComm 2011, 13, 3947. (c) LaDuca, R. L. Coord. Chem. Rev. 2009, 253, 1759. (d) Carlucci, L.; Ciani, G.; Maggini, S.; Proserpio, D. M. Cryst. Growth Des. 2008, 8, 162. (e) Ke, X. J.; Li, D. S.; Du, M. Inorg. Chem. Commun. 2011, 14, 788. (f) Yang, G. P.; Zhou, J. H.; Wang, Y. Y.; Liu, P.; Shi, C. C.; Fu, A. Y.; Shi, Q. Z. CrystEngComm 2011, 13, 33. (g) Ma, L. F.; Wang, L. Y.; Du, M.; Batten, S. R. Inorg. Chem. 2010, 49, 365. (9) (a) Du, M.; Zhang, Z. H.; Tang, L. F.; Zhao, X. J.; Batten, S. R. Chem.Eur. J. 2007, 13, 2578. (b) Li, D. S.; Wu, Y. P.; Zhang, P.; Du, M.; Zhao, J.; Li, C. P.; Wang, Y. Y. Cryst. Growth Des. 2010, 10, 2037. (c) Fu, F.; Li, D. S.; Wu, Y. P.; Gao, X. M.; Du, M.; Tang, L.; Zhang, X. N.; Meng, C. X. CrystEngComm 2010, 12, 1227. (d) Li, D. S.; Ke, X. J.; Zhao, J.; Du, M.; Zou, K.; He, Q. F.; Li, C. CrystEngComm 2011, 13, 3355. (e) Li, D. S.; Fu, F.; Zhao, J.; Wu, Y. P.; Du, M.; Zou, K.; Dong, W. W.; Wang, Y. Y. Dalton Trans. 2010, 39, 11522. (f) Zhang, M. L.; Li, D. S.; Wang, J. J.; Fu, F.; Du, M.; Zou, K.; Gao, X. M. Dalton Trans. 2009, 5355. (g) Gao, X. M.; Li, D. S.; Wang, J. J.; Fu, F.; Wu, Y. P.; Hu, H. M.; Wang, J. W. CrystEngComm 2008, 10, 479. (10) Preparation of 1. A mixture of H3EtIDC (18.4 mg, 0.1 mmol), Cd(NO3)2·4H2O (30.8 mg, 0.1 mmol), bix (23.8 mg, 0.1 mmol), NaOH (4.0 mg, 0.1 mmol), and H2O (8 mL) was placed in a Parr Teflon-lined stainless steel (25 mL) autoclave, heated to 140 °C for 4 days, and then naturally cooled to room temperature. Colorless crystals were obtained in a yield of 40% (based on CdII). Element analysis (%) for C14H15CdN4O5 (1): Calcd, C 38.95, H 3.50, N 12.98; Found, C 39.37, H 3.35, N 12.88. IR (cm−1): 3498s, 2933w, 1619s, 1518s, 1375m, 1251m, 1070w, 844w, 800m, 668s, 651m. Preparation of 2. A similar procedure to that of 1 was used except that bix was replaced by dpe (18.2 mg, 0.1 mmol). Colorless block crystals of 2 were obtained in 47% yield (based on CdII). Element analysis (%) for C26H24Cd2N6O9 (2): Calcd, C 39.56, H 3.06, N 10.65; Found: C 39.76, H 2.86, N 10.53. IR (cm−1): 3453s, 2915w, 1608m, 1528s, 1390m, 1257s, 1014w, 974w, 827m, 787m, 679w. (11) Crystal data for 1 (CCDC-861427): C14H15CdN4O5, Mr = 431.70, tetragonal, I4̅, a = 18.795(12), b = 18.795(12), c = 9.100 (8) Å, V = 3215(4) Å3, Z = 8, ρ = 1.780 g·cm−3, GOF = 1.048, R1 = 0.0332, and wR 2 = 0.0814. Crystal data for 2 (CCDC-861428): C26H24Cd2N6O9, Mr = 789.32, orthorhombic, Pbca, a = 9.7939(7), b = 21.680(17), c = 27.677(2) Å, V = 5878.8(8) Å3, Z = 8, ρ = 1.779 g·cm−3, GOF = 1.017, R1 = 0.0424, and wR2 = 0.0963. (12) (a) Yang, M.; Jiang, F.; Chen, Q.; Zhou, Y.; Feng, R.; Xiong, K.; Hong, M. CrystEngComm 2011, 13, 3971. (b) Guo, H. D.; Qiu, D. F.; Guo, X. M.; Batten, S. R.; Zhang, H. J. CrystEngComm 2009, 11, 2611. (13) (a) Xu, B.; Lin, Z. J.; Han, L. W.; Cao, R. CrystEngComm 2011, 13, 440. (b) Yang, J.; Ma, J. F.; Liu, Y. Y.; Batten, S. R. CrystEngComm 2009, 11, 151. (c) Zhang, J.; Chew, E.; Chen, S.; Pham, J. T. H.; Bu, X. Inorg. Chem. 2008, 47, 3495. (14) (a) Ni, J.; Wei, K. J.; Liu, Y.; Huang, X. C.; Li, D. Cryst. Growth Des. 2010, 10, 3964. (b) Fan, J.; Sun, W. Y.; Okamura, T.; Tang, W. X.; Ueyama, N. Inorg. Chem. 2003, 42, 3168. (c) Barnett, S. A.; Blake, A. J.; Champness, N. R.; Nicolson, J. E. B.; Wilson, C. J. Chem. Soc., Dalton Trans. 2001, 567. (d) Wan, S. Y.; Fan, J.; Okamura, T.; Zhu, H. F.; Ouyang, X. M.; Sun, W. Y.; Ueyama, N. Chem. Commun. 2002, 2520. (e) Wu, H.; Liu, H. Y.; Liu, Y. Y.; Yang, J.; Liu, B.; Ma, J. F. Chem. Commun. 2011, 47, 1818. (15) (a) Qi, Y.; Xia, Y. X.; Zheng, J. M. Cryst. Growth Des. 2008, 8, 3602. (b) Jia, Q. X.; Wang, Y. Q.; Yue, Q.; Wang, Q. L.; Gao, E. Q. Chem. Commun. 2008, 4894. (c) Su, Z.; Fan, J.; Okamura, T.; Chen, M. S.; Chen, S. S.; Sun, W. Y.; Ueyama, N. Cryst. Growth Des. 2010, 10, 1911. (d) Chen, P. K.; Qi, Y.; Che, Y. X.; Zheng, J. M. CrystEngComm 2010, 12, 720. (e) Zhao, J.; Li, D. S.; Hu, Z. Z.; Dong, W. W.; Zou, K.; Lu, J. K. Inorg. Chem. Commun. 2011, 14, 771.

ASSOCIATED CONTENT

S Supporting Information *

Crystallographic data in CIF format, experimental details, a table of bond geometries, supplementary figures, XRPD patterns, TG curves, and solid-state luminescence spectra for 1 and 2. This material is available free of charge via the Internet at http://pubs.acs.org.

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AUTHOR INFORMATION

Corresponding Author

*E-mail: [email protected]. Telephone/Fax: +86-7176397516 (D.-S.L.). E-mail: [email protected]. Telephone/Fax: +86-22-23766556 (M.D.). Notes

The authors declare no competing financial interest.

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ACKNOWLEDGMENTS This work was financially supported by the NSF of China (No: 21073106), the IPHPEO (Q20101203), and the NSF of Hubei Provinces of China (2010CDB10707 and 2011CDA118). M.D. also acknowledges the support from Tianjin Normal University.

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