- Email: [email protected]
A new 3D metal-organic framework (MOF) Zn(DNBPDC)2(BPY) with a dinuclear zinc (II) clusters as SBU
Journal of Molecular Structure 1134 (2017) 59e62
Contents lists available at ScienceDirect
Journal of Molecular Structure journal homepage: http://www.elsevier.com/locate/molstruc
A new 3D metal-organic framework (MOF) Zn(DNBPDC)2(BPY) with a dinuclear zinc (II) clusters as SBU Song Li a, b, Xiangdong Qin a, b, Linxin Deng c, Hui Liu d, * a
College of Basic Science and Information Engineering, Yunnan Agricultural University, Kunming, 650201, China Engineering and Research Center for Industrial Biogas Technology of Yunnan Province University, Kunming, 650201, China c Yunnan Police Officer Academy, Kunming, 650221, China d School of Materials Science and Engineering, Wuhan Institute of Technology, Wuhan, 430073, China b
a r t i c l e i n f o
a b s t r a c t
Article history: Received 21 September 2016 Received in revised form 9 December 2016 Accepted 14 December 2016 Available online 22 December 2016
A new 3D framework compound 1 Zn(DNBPDC)2(BPY) (DBDBC ¼2,20 -dinitro-[1,10 -biphenyl]-4,40 -dicarboxylic acid, BPY ¼ 4,40 -Bipyridine) with a dinuclear zinc (II) clusters as SBU have been synthesized and structurally characterized. This compound crystallizes in Tetragonal, space group I41/acd, with a ¼ 21.2959(10)Å, b ¼ 21.2959(10) Å, c ¼ 27.969(3) Å, a ¼ 90.00 , b ¼ 90.00 (10) , g ¼ 90.00 , V ¼12684.4(16) Å3, Z ¼ 16, Dc ¼ 1.424 mg/cm3, m ¼ 0.806 mm1, F(000) ¼ 3792. From the thermogravimetric analysis, the compound can be stabilized up to 380 C and the skeleton collapsed occurred in about 350e550 C. The luminescence property test shows that the compound exhibit strong emission at 485 nm. The nitrogen adsorption capacity was 10 cc/g when the compound was activated under the temperature of 77 K and reach to atmospheric pressure. © 2016 Elsevier B.V. All rights reserved.
Keywords: Metal-organic framework Zinc complex Fluorescence Gas adsorption
1. Introduction
2. Experimental
Metaleorganic frameworks (MOFs), also known as coordination polymers, are crystalline coordination-based compounds in which metallic centers are bridged via organic multitopic ligands to form multi-dimensional networks [1]. MOFs have attached extensive attention over the last decades, due to their potential applications in gas storage [2,3], separation of small gases and hydrocarbons [4,5], catalysis [6,7], sensors [8,9], magnetism [10], membrane fillers [11] and luminescence [12]. Current and intensive researches have been focused on how to design and synthetize MOFs with new structures in order to increase their quantity and improve performances [13e16]. Now, a large various types of network structures have been rationally designed and synthesized through the constructed metal building block and organic ligands [17e20]. In this paper, we choose the carboxylic acid DNBPDC and BPY as ligands to synthesized a new MOFs compound 1 Zn(DNBPDC)2 (BPY)with new SBU, then we characterized the compound's chemical properties systematically such as structural analysis, luminescent test and gas adsorption test.
2.1. Materials and instruments
* Corresponding author. E-mail address: [email protected] (H. Liu). http://dx.doi.org/10.1016/j.molstruc.2016.12.036 0022-2860/© 2016 Elsevier B.V. All rights reserved.
All chemicals used in the syntheses were commercially available reagents of analytical grade and were used without further purification. The data for crystals were collected on a Bruker APEX-II CCD diffractometer (MoKa, l ¼ 0.71073 Å) at 298(2) K. Infrared spectra (KBr pellets) were taken on a Bruke Tensor 27 FTIR spectrometer in the range of 4000e400 cm1. Luminescent properties of compounds were recorded on an F-4500 fluorescence spectrometer under room temperature.
2.2. Synthesis of compound 1 Hydro-thermal method was used for the synthesis of compound 1, as reported in the relevant literature [21]. A mixture of 2,20 dinitro-[1,10 -biphenyl]-4,40 -dicarboxylic acid (0.1 mmol), Zn(NO3)2$6H2O(0.1 mmol), 4,40 -bpy (0.1 mmol), H2O (10 mL) and methanol (2 mL) was stirred for 20 min and then sealed in a 25 mL Teflon-lined stainless steel autoclave and heated at 130 C for 48 h. yellow block crystals of compound 1 were obtained, which were washed with water and dried in air with a 65% yield.
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S. Li et al. / Journal of Molecular Structure 1134 (2017) 59e62
2.3. Structure determination The suitable crystals of compound 1 were selected for X-ray diffraction study. Diffraction data were collected on a Bruker SMART APEX-II CCD diffractometer equipped with a graphitemonochromated Mo-Ka radiation (l ¼ 0.71073 Å) by r-u diffraction data at 298(2) K. All diffraction data were handled through the SADABS software with multi-scan semi-empirical method of absorption correction. The structure was solved by direct methods and subsequent successive difference Fourier maps, and refined by full-matrix least-squares techniques on F2 using SHELX L-97 program. A summary of the crystallographic data and structure refinement of compound 1 are listed in Table 1 and the selected bond lengths and bond angels are listed in Table 2. CCDC: 845806 for compound 1. 3. Results and discussion 3.1. Crystal structures of compound 1
Fig. 1. SBUs of compound 1.
Single X-ray crystal diffraction analysis reveals that compound 1 crystallizes in the I41/acd space group, and possesses an extended 3D framework with a dinuclear Zinc clusters as secondly build unit within which Two Zn2þ connecting four O and two N atoms forms a cage center. In the dinuclear Zinc unit, each Zn2þ is connected by four oxygen atoms which come from four DNBPDCs ligand each. As shown in Fig. 1. The distances of Zn-O are 1.98 Å and 2.02 Å. Each of the opposite DNBPDCs ligand are not on a flat surface, respectively rotating 45 from the plane in different directions that are Clockwise and anticlockwise. Four DNBPDCs ligand spread out to form a 2D layer and two BPY molecules serve as pillar-ligands to coordinate the outer Zn atoms which gives raise to 3D framework (Fig. 2). 3.2. Microscope and SEM characterization The morphology of compound 1 was tested by microscope and scanning electron microscope using methods as the relevant literature [22]. Fig. 3 is the microscopic image of compound 1, white acicular crystal compounds and a small amount of bulk crystals can
be seen in it. And Fig. 4 is the scanning electron microscope image of compound 1. As in the image, the compound has a surface appearance of elongated sheet structure.
3.3. Thermal stability analysis In order to detect the thermal stability of compound 1, thermogravimetric analysis was tested under nitrogen atmosphere and the performance is consistent with the relevant literature [23], the temperature range is 0e600 C. Fig. 5 is the TG result of compound 1. It can be seen from the figure that the compound can be stabilized up to 380 C. The first weight loss occurred in about the temperature range of 200e300 C and the weight loss ratio was 6.26%, this could be attributed to the guest molecules lost. The skeleton collapsed occurred in about the temperature range of 350e550 C and the weight loss ratio was 63.38%. The final decomposition product remaining was ZnO of a 30.36% ratio.
Table 1 Crystal data and structure refinements of the title compound 1. 1
1 C25H20N5O14Zn 679.5 0.48 0.41 0.38 2.26 to 27 Tetragonal I41/acd 21.2959(10) 21.2959(10) 27.969(3) 90.00 90.00 90.00 12684.4(16)
Empirical formula Formula weight Size/mm q rang for data collection/( ) Crystal system Space group a/Å b/Å c/Å a/( ) b/( ) g/( ) V/nm3
Z
m/nm1 3
Dc/(mg.cm ) F(000) Reflections collected Independent reflections(Rint) Goodness of fit on F2 R1,wR2(I > 2s(I) R1,wR2(all data) Drmax(eÅ3) Drmin (eÅ3)
16 0.806 1.424 3792 2861 3214(0.038) 0.932 0.1457,0.2874 0.1638,0.2919 2.386 1.234
Table 2 Selected bond lengths(Å) and angles( ) for the title compound 1. Zn1dO1
1.98521(14)
O1dZn1dO1 O1dZn1dO2 O2dZn1dO2
159.658(5) 88.144(4) 155.752(5)
Zn1dN1
2.0053(2)
Zn1dO2
O1dZn1dN1 N1dZn1dO2
100.171(3) 102.124(2)
2.01921(14)
S. Li et al. / Journal of Molecular Structure 1134 (2017) 59e62
61
Fig. 5. The TGA curve of compound 1. Fig. 2. The 3D framework structure of compound 1.
the relevant literature [24], as shown in Fig. 6. Upon excitation at 350 nm, compound 1 shows strong emission maxima at 485 nm. The emission bands may result from intra ligand p/p* transition between the p-bonding orbital (highest occupied molecular orbital, HOMO) and the p*-antibonding orbital (lowest unoccupied molecular orbital, LUMO) of the carboxylic ligands, rather than metalto-ligand charge transfer (MLCT) or ligand-to-metal charge transfer (LMCT). The blue shift may be assigned to the nature of the ligand bonding (chelating or bridging) to the ZnII center, which changes the rigidity and conjugation of the ligands. Under same condition, we also realized the emission intensity of the compound increased markedly compared with free DNBPDC ligand. This compound displays photoluminescence in the blue region, which suggests potential as blue-light-emitting material.
3.5. Gas adsorption properties Fig. 3. The microscopic image of compound 1.
The nitrogen adsorption of this compound after activated was measured under the temperature of 77 K testing result shown as in Fig. 7. This compound showed a typical type III of isothermal adsorption curve to nitrogen [25]. The initial stage of adsorbate's
Fig. 4. The scanning electron microscope image of compound 1.
3.4. Luminescent properties The photoluminescence properties of compound 1 have been explored at room temperature in the solid state using methods as
Fig. 6. Photoluminescence properties of compound 1.
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S. Li et al. / Journal of Molecular Structure 1134 (2017) 59e62
Acknowledgements This work is supported by the Scientific Research Foundation of Yunnan Provincial Education Department (No. 2016zzx107). Appendix A. Supplementary data Supplementary data related to this article can be found at http:// dx.doi.org/10.1016/j.molstruc.2016.12.036. References
Fig. 7. Gas adsorption curves of compound 1.
adsorption was difficult and with the adsorption process carrying on, the adsorption appears to be a self-accelerating phenomenon, the higher the relative pressure, the more adsorption capacity, shows a hole filling quality. The nitrogen adsorption capacity was 10 cc/g when reach to atmospheric pressure.
4. Conclusions In summary, a new 3D framework MOF Zn(DNBPDC)2(BPY)with a dinuclear zinc (II) clusters as SBU have been synthesized and structurally characterized. Other chemical properties were characterized systematically. This work may give an impetus to the further design and exploration of new structure MOF.
[1] M.P. Suh, H.J. Park, T.K. Prasad, et al., Chem. Rev. Wash. DC, U. S.) 112 (2) (2012) 782e835. [2] O.M. Yaghi, J.L.C. Rowsell, A.R. Millward, et al., J. Am. Chem. Soc. 126 (18) (2004) 5666e5667. [3] N.L. Rosi, J. Eckert, M. Eddaoudi, et al., Science 300 (5622) (2003) 1127e1129. [4] J.M. Zhang, H.H. Wu, T.J. Emge, et al., Chem. Commun. Camb. U. K.) 46 (48) (2010) 9152e9154. [5] K.H. Li, D.H. Olsan, J.Y. Lee, et al., Adv. Funct. Mater. 18 (15) (2008) 2205e2214. [6] J.-R. Li, J. Sculley, H.-C. Zhou, Chem. Rev. Wash. DC, U. S.) 112 (2) (2012) 869e932. [7] B.Z. Yuan, Y.Y. Pan, Y.W. Li, et al., Angew. Chem. Int. Ed. 49 (24) (2010) 4054e4058. [8] M. Yoon, R. Srirambalaji, K. Kim, Chem. Rev. Wash. DC, U. S.) 112 (2) (2012) 1196e1231. [9] J. Li, S. Pramanik, C. Zheng, et al., J. Am. Chem. Soc. 133 (12) (2011) 4153e4155. [10] A.J. Lan, K.H. Li, H.H. Wu, et al., Angew. Chem. Int. Ed. 48 (13) (2009) 2334e2338. [11] L.E. Kreno, K. Leong, O.K. Farha, et al., Chem. Rev. Wash. DC, U. S.) 112 (2) (2012) 1105e1125. [12] X.M. Zhang, Z.M. Hao, W.X. Zhang, et al., Angew. Chem. Int. Ed. 46 (19) (2007) 3456e3459. [13] Y. Cui, Y. Yue, G. Qian, et al., Chem. Rev. Wash. DC, U. S.) 112 (2) (2012) 1126e1162. [14] S.M. Cohen, Chem. Rev. Wash. DC, U. S.) 112 (2) (2012) 970e1000. [15] M. O'keeffe, O.M. Yaghi, Chem. Rev. Wash. DC, U. S.) 112 (2) (2012) 675e702. [16] T. PaNPA, P. Pachfule, Y.F. Chen, et al., Chem. Commun. Camb. U. K.) 47 (7) (2011) 2011e2013. [17] H. Liu, Y.G. Zhao, Z.J. Zhang, et al., Adv. Funct. Mater. 21 (24) (2011) 4754e4762. [18] H. Liu, Y. Zhao, Z. Zhang, et al., Chem. e An Asian J. 8 (4) (2013) 778e785. [19] Ashlee J. Howarth, et al., Nat. Rev. Mater. 1 (2016) 15018. [20] Manjula I. Nandasiri, et al., Coord. Chem. Rev. 311 (2016) 38e52. [21] Yu-Ri Lee, Jun Kim, Wha-Seung Ahn, Korean J. Chem. Eng. 30 (9) (2013) 1667e1680. [22] Ya-Nan Guo, et al., RSC Adv. 2 (12) (2012) 5424e5429. [23] Peng Ren, Wei Shi, Peng Cheng, Cryst. Growth Des. 8 (4) (2008) 1097e1099. [24] M.D. Allendorf, et al., Chem. Soc. Rev. 38 (5) (2009) 1330e1352. [25] Yingwei Li, Ralph T. Yang, Langmuir 23 (26) (2007) 12937e12944.
Contents lists available at ScienceDirect
Journal of Molecular Structure journal homepage: http://www.elsevier.com/locate/molstruc
A new 3D metal-organic framework (MOF) Zn(DNBPDC)2(BPY) with a dinuclear zinc (II) clusters as SBU Song Li a, b, Xiangdong Qin a, b, Linxin Deng c, Hui Liu d, * a
College of Basic Science and Information Engineering, Yunnan Agricultural University, Kunming, 650201, China Engineering and Research Center for Industrial Biogas Technology of Yunnan Province University, Kunming, 650201, China c Yunnan Police Officer Academy, Kunming, 650221, China d School of Materials Science and Engineering, Wuhan Institute of Technology, Wuhan, 430073, China b
a r t i c l e i n f o
a b s t r a c t
Article history: Received 21 September 2016 Received in revised form 9 December 2016 Accepted 14 December 2016 Available online 22 December 2016
A new 3D framework compound 1 Zn(DNBPDC)2(BPY) (DBDBC ¼2,20 -dinitro-[1,10 -biphenyl]-4,40 -dicarboxylic acid, BPY ¼ 4,40 -Bipyridine) with a dinuclear zinc (II) clusters as SBU have been synthesized and structurally characterized. This compound crystallizes in Tetragonal, space group I41/acd, with a ¼ 21.2959(10)Å, b ¼ 21.2959(10) Å, c ¼ 27.969(3) Å, a ¼ 90.00 , b ¼ 90.00 (10) , g ¼ 90.00 , V ¼12684.4(16) Å3, Z ¼ 16, Dc ¼ 1.424 mg/cm3, m ¼ 0.806 mm1, F(000) ¼ 3792. From the thermogravimetric analysis, the compound can be stabilized up to 380 C and the skeleton collapsed occurred in about 350e550 C. The luminescence property test shows that the compound exhibit strong emission at 485 nm. The nitrogen adsorption capacity was 10 cc/g when the compound was activated under the temperature of 77 K and reach to atmospheric pressure. © 2016 Elsevier B.V. All rights reserved.
Keywords: Metal-organic framework Zinc complex Fluorescence Gas adsorption
1. Introduction
2. Experimental
Metaleorganic frameworks (MOFs), also known as coordination polymers, are crystalline coordination-based compounds in which metallic centers are bridged via organic multitopic ligands to form multi-dimensional networks [1]. MOFs have attached extensive attention over the last decades, due to their potential applications in gas storage [2,3], separation of small gases and hydrocarbons [4,5], catalysis [6,7], sensors [8,9], magnetism [10], membrane fillers [11] and luminescence [12]. Current and intensive researches have been focused on how to design and synthetize MOFs with new structures in order to increase their quantity and improve performances [13e16]. Now, a large various types of network structures have been rationally designed and synthesized through the constructed metal building block and organic ligands [17e20]. In this paper, we choose the carboxylic acid DNBPDC and BPY as ligands to synthesized a new MOFs compound 1 Zn(DNBPDC)2 (BPY)with new SBU, then we characterized the compound's chemical properties systematically such as structural analysis, luminescent test and gas adsorption test.
2.1. Materials and instruments
* Corresponding author. E-mail address: [email protected] (H. Liu). http://dx.doi.org/10.1016/j.molstruc.2016.12.036 0022-2860/© 2016 Elsevier B.V. All rights reserved.
All chemicals used in the syntheses were commercially available reagents of analytical grade and were used without further purification. The data for crystals were collected on a Bruker APEX-II CCD diffractometer (MoKa, l ¼ 0.71073 Å) at 298(2) K. Infrared spectra (KBr pellets) were taken on a Bruke Tensor 27 FTIR spectrometer in the range of 4000e400 cm1. Luminescent properties of compounds were recorded on an F-4500 fluorescence spectrometer under room temperature.
2.2. Synthesis of compound 1 Hydro-thermal method was used for the synthesis of compound 1, as reported in the relevant literature [21]. A mixture of 2,20 dinitro-[1,10 -biphenyl]-4,40 -dicarboxylic acid (0.1 mmol), Zn(NO3)2$6H2O(0.1 mmol), 4,40 -bpy (0.1 mmol), H2O (10 mL) and methanol (2 mL) was stirred for 20 min and then sealed in a 25 mL Teflon-lined stainless steel autoclave and heated at 130 C for 48 h. yellow block crystals of compound 1 were obtained, which were washed with water and dried in air with a 65% yield.
60
S. Li et al. / Journal of Molecular Structure 1134 (2017) 59e62
2.3. Structure determination The suitable crystals of compound 1 were selected for X-ray diffraction study. Diffraction data were collected on a Bruker SMART APEX-II CCD diffractometer equipped with a graphitemonochromated Mo-Ka radiation (l ¼ 0.71073 Å) by r-u diffraction data at 298(2) K. All diffraction data were handled through the SADABS software with multi-scan semi-empirical method of absorption correction. The structure was solved by direct methods and subsequent successive difference Fourier maps, and refined by full-matrix least-squares techniques on F2 using SHELX L-97 program. A summary of the crystallographic data and structure refinement of compound 1 are listed in Table 1 and the selected bond lengths and bond angels are listed in Table 2. CCDC: 845806 for compound 1. 3. Results and discussion 3.1. Crystal structures of compound 1
Fig. 1. SBUs of compound 1.
Single X-ray crystal diffraction analysis reveals that compound 1 crystallizes in the I41/acd space group, and possesses an extended 3D framework with a dinuclear Zinc clusters as secondly build unit within which Two Zn2þ connecting four O and two N atoms forms a cage center. In the dinuclear Zinc unit, each Zn2þ is connected by four oxygen atoms which come from four DNBPDCs ligand each. As shown in Fig. 1. The distances of Zn-O are 1.98 Å and 2.02 Å. Each of the opposite DNBPDCs ligand are not on a flat surface, respectively rotating 45 from the plane in different directions that are Clockwise and anticlockwise. Four DNBPDCs ligand spread out to form a 2D layer and two BPY molecules serve as pillar-ligands to coordinate the outer Zn atoms which gives raise to 3D framework (Fig. 2). 3.2. Microscope and SEM characterization The morphology of compound 1 was tested by microscope and scanning electron microscope using methods as the relevant literature [22]. Fig. 3 is the microscopic image of compound 1, white acicular crystal compounds and a small amount of bulk crystals can
be seen in it. And Fig. 4 is the scanning electron microscope image of compound 1. As in the image, the compound has a surface appearance of elongated sheet structure.
3.3. Thermal stability analysis In order to detect the thermal stability of compound 1, thermogravimetric analysis was tested under nitrogen atmosphere and the performance is consistent with the relevant literature [23], the temperature range is 0e600 C. Fig. 5 is the TG result of compound 1. It can be seen from the figure that the compound can be stabilized up to 380 C. The first weight loss occurred in about the temperature range of 200e300 C and the weight loss ratio was 6.26%, this could be attributed to the guest molecules lost. The skeleton collapsed occurred in about the temperature range of 350e550 C and the weight loss ratio was 63.38%. The final decomposition product remaining was ZnO of a 30.36% ratio.
Table 1 Crystal data and structure refinements of the title compound 1. 1
1 C25H20N5O14Zn 679.5 0.48 0.41 0.38 2.26 to 27 Tetragonal I41/acd 21.2959(10) 21.2959(10) 27.969(3) 90.00 90.00 90.00 12684.4(16)
Empirical formula Formula weight Size/mm q rang for data collection/( ) Crystal system Space group a/Å b/Å c/Å a/( ) b/( ) g/( ) V/nm3
Z
m/nm1 3
Dc/(mg.cm ) F(000) Reflections collected Independent reflections(Rint) Goodness of fit on F2 R1,wR2(I > 2s(I) R1,wR2(all data) Drmax(eÅ3) Drmin (eÅ3)
16 0.806 1.424 3792 2861 3214(0.038) 0.932 0.1457,0.2874 0.1638,0.2919 2.386 1.234
Table 2 Selected bond lengths(Å) and angles( ) for the title compound 1. Zn1dO1
1.98521(14)
O1dZn1dO1 O1dZn1dO2 O2dZn1dO2
159.658(5) 88.144(4) 155.752(5)
Zn1dN1
2.0053(2)
Zn1dO2
O1dZn1dN1 N1dZn1dO2
100.171(3) 102.124(2)
2.01921(14)
S. Li et al. / Journal of Molecular Structure 1134 (2017) 59e62
61
Fig. 5. The TGA curve of compound 1. Fig. 2. The 3D framework structure of compound 1.
the relevant literature [24], as shown in Fig. 6. Upon excitation at 350 nm, compound 1 shows strong emission maxima at 485 nm. The emission bands may result from intra ligand p/p* transition between the p-bonding orbital (highest occupied molecular orbital, HOMO) and the p*-antibonding orbital (lowest unoccupied molecular orbital, LUMO) of the carboxylic ligands, rather than metalto-ligand charge transfer (MLCT) or ligand-to-metal charge transfer (LMCT). The blue shift may be assigned to the nature of the ligand bonding (chelating or bridging) to the ZnII center, which changes the rigidity and conjugation of the ligands. Under same condition, we also realized the emission intensity of the compound increased markedly compared with free DNBPDC ligand. This compound displays photoluminescence in the blue region, which suggests potential as blue-light-emitting material.
3.5. Gas adsorption properties Fig. 3. The microscopic image of compound 1.
The nitrogen adsorption of this compound after activated was measured under the temperature of 77 K testing result shown as in Fig. 7. This compound showed a typical type III of isothermal adsorption curve to nitrogen [25]. The initial stage of adsorbate's
Fig. 4. The scanning electron microscope image of compound 1.
3.4. Luminescent properties The photoluminescence properties of compound 1 have been explored at room temperature in the solid state using methods as
Fig. 6. Photoluminescence properties of compound 1.
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S. Li et al. / Journal of Molecular Structure 1134 (2017) 59e62
Acknowledgements This work is supported by the Scientific Research Foundation of Yunnan Provincial Education Department (No. 2016zzx107). Appendix A. Supplementary data Supplementary data related to this article can be found at http:// dx.doi.org/10.1016/j.molstruc.2016.12.036. References
Fig. 7. Gas adsorption curves of compound 1.
adsorption was difficult and with the adsorption process carrying on, the adsorption appears to be a self-accelerating phenomenon, the higher the relative pressure, the more adsorption capacity, shows a hole filling quality. The nitrogen adsorption capacity was 10 cc/g when reach to atmospheric pressure.
4. Conclusions In summary, a new 3D framework MOF Zn(DNBPDC)2(BPY)with a dinuclear zinc (II) clusters as SBU have been synthesized and structurally characterized. Other chemical properties were characterized systematically. This work may give an impetus to the further design and exploration of new structure MOF.
[1] M.P. Suh, H.J. Park, T.K. Prasad, et al., Chem. Rev. Wash. DC, U. S.) 112 (2) (2012) 782e835. [2] O.M. Yaghi, J.L.C. Rowsell, A.R. Millward, et al., J. Am. Chem. Soc. 126 (18) (2004) 5666e5667. [3] N.L. Rosi, J. Eckert, M. Eddaoudi, et al., Science 300 (5622) (2003) 1127e1129. [4] J.M. Zhang, H.H. Wu, T.J. Emge, et al., Chem. Commun. Camb. U. K.) 46 (48) (2010) 9152e9154. [5] K.H. Li, D.H. Olsan, J.Y. Lee, et al., Adv. Funct. Mater. 18 (15) (2008) 2205e2214. [6] J.-R. Li, J. Sculley, H.-C. Zhou, Chem. Rev. Wash. DC, U. S.) 112 (2) (2012) 869e932. [7] B.Z. Yuan, Y.Y. Pan, Y.W. Li, et al., Angew. Chem. Int. Ed. 49 (24) (2010) 4054e4058. [8] M. Yoon, R. Srirambalaji, K. Kim, Chem. Rev. Wash. DC, U. S.) 112 (2) (2012) 1196e1231. [9] J. Li, S. Pramanik, C. Zheng, et al., J. Am. Chem. Soc. 133 (12) (2011) 4153e4155. [10] A.J. Lan, K.H. Li, H.H. Wu, et al., Angew. Chem. Int. Ed. 48 (13) (2009) 2334e2338. [11] L.E. Kreno, K. Leong, O.K. Farha, et al., Chem. Rev. Wash. DC, U. S.) 112 (2) (2012) 1105e1125. [12] X.M. Zhang, Z.M. Hao, W.X. Zhang, et al., Angew. Chem. Int. Ed. 46 (19) (2007) 3456e3459. [13] Y. Cui, Y. Yue, G. Qian, et al., Chem. Rev. Wash. DC, U. S.) 112 (2) (2012) 1126e1162. [14] S.M. Cohen, Chem. Rev. Wash. DC, U. S.) 112 (2) (2012) 970e1000. [15] M. O'keeffe, O.M. Yaghi, Chem. Rev. Wash. DC, U. S.) 112 (2) (2012) 675e702. [16] T. PaNPA, P. Pachfule, Y.F. Chen, et al., Chem. Commun. Camb. U. K.) 47 (7) (2011) 2011e2013. [17] H. Liu, Y.G. Zhao, Z.J. Zhang, et al., Adv. Funct. Mater. 21 (24) (2011) 4754e4762. [18] H. Liu, Y. Zhao, Z. Zhang, et al., Chem. e An Asian J. 8 (4) (2013) 778e785. [19] Ashlee J. Howarth, et al., Nat. Rev. Mater. 1 (2016) 15018. [20] Manjula I. Nandasiri, et al., Coord. Chem. Rev. 311 (2016) 38e52. [21] Yu-Ri Lee, Jun Kim, Wha-Seung Ahn, Korean J. Chem. Eng. 30 (9) (2013) 1667e1680. [22] Ya-Nan Guo, et al., RSC Adv. 2 (12) (2012) 5424e5429. [23] Peng Ren, Wei Shi, Peng Cheng, Cryst. Growth Des. 8 (4) (2008) 1097e1099. [24] M.D. Allendorf, et al., Chem. Soc. Rev. 38 (5) (2009) 1330e1352. [25] Yingwei Li, Ralph T. Yang, Langmuir 23 (26) (2007) 12937e12944.