Citation: Liu Zun-Qi, Liu Yang, Chen Yuan, Zhao Wu-Qiang, Fang Wei-Na. Synthesis, characterization, and phase transition of an inorganic-organic hybrid compound, [(3-nitroanilinium+) (18-crown-6)] [IO4-](CH3OH)[J]. Chinese Chemical Letters, ;2017, 28(2): 297-301. doi: 10.1016/j.cclet.2016.07.013 shu

Synthesis, characterization, and phase transition of an inorganic-organic hybrid compound, [(3-nitroanilinium+) (18-crown-6)] [IO4-](CH3OH)

  • Corresponding author: Liu Zun-Qi, zunqi85@163.com
  • Received Date: 11 June 2016
    Revised Date: 21 June 2016
    Accepted Date: 4 July 2016
    Available Online: 18 February 2016

Figures(7)

  • A novel inorganic-organic hybrid supramolecular compound, [(3-nitroanilinium+)(18-crown-6)] [IO4-](CH3OH) (1), was discovered as phase-transition materials displaying dielectric anomalous behaviors. The yellow block crystal formed by N-H…O hydrogen bonding that made contact through the cavity of 18-crown-6 was characterized by single-crystal X-ray diffraction, elemental analysis, infrared analysis, thermogravimetric analysis, differential scanning calorimetry, and potential-energy calculations. Differential scanning calorimetry measurements indicate that the compound experiences a reversible phase transition at around 220 K. Temperature-dependent dielectric measurements further confirm the phase transitions. Potential-energy calculations demonstrate that the phase transition occurs due to the molecular order-disorder rotation of CH3OH, whereas the space grouping of the crystal remains unchanged.
  • 加载中
    1. [1]

      T. Hang, W. Zhang, H.Y. Ye, R.G. Xiong. Metal-organic complex ferroelectrics[J]. Chem. Soc. Rev., 2011,40:3577-3598. doi: 10.1039/c0cs00226g

    2. [2]

      D.W. Fu, H.L. Cai, Y.M. Liu. Diisopropylammonium bromide is a hightemperature molecular ferroelectric crystal[J]. Science, 2013,339:425-428. doi: 10.1126/science.1229675

    3. [3]

      S. Nishihara, T. Akutagawa, T. Hasegawa, T. Nakamura, Formation of a molecular spin ladder induced by a supramolecular cation structure, Chem. Commun. (2002) 408-409.

    4. [4]

      W. Zhang, H.Y. Ye, H.L. Cai. :[H2dbco]2[Cl3] [CuCl3(H2O)2] H2O (dbco=1, 4-Diaza-bicyclo[2.2.2] octane)[J]. J. Am. Chem. Soc., 2010,132:7300-7302. doi: 10.1021/ja102573h

    5. [5]

      H.Y. Ye, Q.H. Zhou, X.H. Niu. High-temperature ferroelectricity and photoluminescence in a hybrid organic-inorganic compound:(3-pyrrolinium) MnCl3[J]. J. Am. Chem. Soc., 2015,137:13148-13154. doi: 10.1021/jacs.5b08290

    6. [6]

      J.Z. Ge, X.Q. Fu, T. Hang, Q. Ye, R.G. Xiong. Reversible phase transition of the 1:1 complexes of 18-crown-6 with 4-ethoxyanilinium perchlorate[J]. Cryst. Growth Des., 2010,10:3632-3637. doi: 10.1021/cg100523b

    7. [7]

      Y. Zhang, H.Y. Ye, D.W. Fu, R.G. Xiong. An order-disorder ferroelectric host-guest inclusion compound[J]. Angew. Chem. Int. Ed., 2014,53:2114-2118. doi: 10.1002/anie.201307690

    8. [8]

      H.Y. Ye, S.H. Li, Y. Zhang. Solid state molecular dynamic investigation of an inclusion ferroelectric:[(2, 6-Diisopropylanilinium)([18] crown-6)]BF4[J]. J. Am. Chem. Soc., 2014,136:10033-10040. doi: 10.1021/ja503344b

    9. [9]

      A. Katrusiak, M. Szafrański. Ferroelectricity in NH... N hydrogen bonded crystals[J]. Phys. Rev. Lett., 1999,82:576-579. doi: 10.1103/PhysRevLett.82.576

    10. [10]

      T. Akutagawa, H. Koshinaka, D. Sato. Ferroelectricity and polarity control in solid-state flip-flop supramolecular rotators[J]. Nat. Mater., 2009,8:342-347. doi: 10.1038/nmat2377

    11. [11]

      D. Sato, T. Akutagawa, S. Takeda, S.I. Noro, T. Nakamura. Supramolecular Rotor:Adamantylammonium ([18] crown-6) in[Ni (dmit)2]- Salt[J]. Inorg. Chem., 2007,46:363-365. doi: 10.1021/ic061831u

    12. [12]

      G.S. Kottas, L.I. Clarke, D. Horinek, J. Michl. Artificial molecular rotors[J]. Chem. Rev., 2005,105:1281-1376. doi: 10.1021/cr0300993

    13. [13]

      G.C. Xu, X.M. Ma, L. Zhang, Z.M. Wang, S. Gao. Disorder-order ferroelectric transition in the metal formate framework of[NH4] [Zn (HCOO)3][J]. J. Am. Chem. Soc., 2010,132:9588-9590. doi: 10.1021/ja104263m

    14. [14]

      P.P. Shi, Q. Ye, Q. Li. Novel phase-transition materials coupled with switchable dielectric, magnetic, and optical properties:[(CH3)4P] [FeCl4] and[(CH3)4P] [FeBr4][J]. Chem. Mater., 2014,26:6042-6049. doi: 10.1021/cm503003f

    15. [15]

      B.K. Singh, N. Sinha, N. Singh. Structural, dielectric, optical and ferroelectric property of urea succinic acid crystals grown in aqueous solution containing maleic acid[J]. J. Phys. Chem. Solids, 2010,71:1774-1779. doi: 10.1016/j.jpcs.2010.09.010

    16. [16]

      Z.H. Sun, T.L. Chen, J.H. Luo, M.C. Hong. Bis (imidazolium) L-tartrate:a hydrogenbonded displacive-type molecular ferroelectric material[J]. Angew. Chem. Int. Ed., 2012,51:3871-3876. doi: 10.1002/anie.v51.16

    17. [17]

      Z.Q. Liu, K. Kubo, S.I. Noro, T. Akutagawa, T. Nakamura. Design of crystalline spaces for molecular rotations in crystals[J]. Cryst. Growth Des., 2014,12:537-543.

    18. [18]

      M. Szafrański, A. Katrusiak. Giant dielectric anisotropy and relaxor ferroelectricity induced by proton transfers in NH+...N-Bonded Supramolecular Aggregates[J]. J. Phys. Chem. B, 2008,112:6779-6785. doi: 10.1021/jp801106m

    19. [19]

      Z.Q. Liu, K. Kubo, L. Lin. Molecular motion in pyridazinium/crown ether supramolecular cation salts of a nickel dithiolene complex[J]. Dalton Trans., 2013,42:2930-2939. doi: 10.1039/C2DT32542J

    20. [20]

      Y.L. Liu, Y.F. Wang, W. Zhang. Switchable dielectric constant in an inclusion compound bis (thiourea) imidazolium chloride[J]. Cryst. Eng. Comm., 2016,18:1958-1963. doi: 10.1039/C5CE02364E

    21. [21]

      H.Y. Ye, H.L. Cai, J.Z. Ge, R.G. Xiong. Isosymmetric temperature-triggered structural phase transition of dabcodiium chlorochromate chloride[J]. Inorg. Chem. Commun., 2012,17:159-162. doi: 10.1016/j.inoche.2011.12.040

    22. [22]

      Q. Ye, P.P. Shi, X.Q. Fu, T. Akutagawa, T. Nakamura. Dielectric and structural phase transition of[Ni (dmit)2]- salt with (4-ethoxyanilinium)([18] crown-6) supramolecular cation[J]. Cryst. Eng. Comm., 2013,15:5307-5313. doi: 10.1039/c3ce40220g

    23. [23]

      Z.Q. Liu, Y. Liu, J.F. Wang, G.F. Yang. A novel proton transfer supramolecular compound induced by N-H...O hydrogen bond through 18-crown-6:syntheses, structures, and dielectric properties[J]. Inorg. Chem. Commun., 2015,61:109-112. doi: 10.1016/j.inoche.2015.08.024

    24. [24]

      G.M. Sheldrick, SHELXS 97, Program for X-ray crystal structure solution and refinement, University of Gottingen, Germany, 1997.

    25. [25]

      A. Altomare, G. Cascarano, C. Giacovazzo. SIRPOW.92-a program for automatic solution of crystal structures by direct methods optimized for powder data[J]. J. Appl. Cryst., 1994,27:435-436.

    26. [26]

      M.J. Frisch, G.W. Trucks, H.B. Schlegel, et al., Gaussian 03, Revision C.02, Gaussian, Inc., Wallingford, CT, 2004.

    27. [27]

      Y. Zhang, H.Y. Ye, H.L. Cai. Switchable dielectric, piezoelectric, and secondharmonic generation bistability in a new improper ferroelectric above room temperature[J]. Adv. Mater., 2014,26:4515-4520. doi: 10.1002/adma.v26.26

    28. [28]

      Y.Z. Tang, Y.M. Yu, J.B. Xiong, Y.H. Tan, H.R. Wen. Unusual high-temperature reversible phase-transition behavior, structures, and dielectric-ferroelectric properties of two new crown ether clathrates[J]. J. Am. Chem. Soc., 2015,137:13345-13351. doi: 10.1021/jacs.5b08061

  • 加载中
    1. [1]

      Tian YangYi LiuLina HuaYaoyao ChenWuqian GuoHaojie XuXi ZengChanghao GaoWenjing LiJunhua LuoZhihua Sun . Lead-free hybrid two-dimensional double perovskite with switchable dielectric phase transition. Chinese Chemical Letters, 2024, 35(6): 108707-. doi: 10.1016/j.cclet.2023.108707

    2. [2]

      Zhaohong ChenMengzhen LiJinfei LanShengqian HuXiaogang Chen . Organic ferroelastic enantiomers with high Tc and large dielectric switching ratio triggered by order-disorder and displacive phase transition. Chinese Chemical Letters, 2024, 35(10): 109548-. doi: 10.1016/j.cclet.2024.109548

    3. [3]

      Zhi-Yuan YueHua-Kai LiNa WangShan-Shan LiuLe-Ping MiaoHeng-Yun YeChao Shi . Dehydration-triggered structural phase transition-associated ferroelectricity in a hybrid perovskite-type crystal. Chinese Chemical Letters, 2024, 35(10): 109355-. doi: 10.1016/j.cclet.2023.109355

    4. [4]

      Ke-Ai Zhou Lian Huang Xing-Ping Fu Li-Ling Zhang Yu-Ling Wang Qing-Yan Liu . Fluorinated metal-organic framework for methane purification from a ternary CH4/C2H6/C3H8 mixture. Chinese Journal of Structural Chemistry, 2023, 42(11): 100172-100172. doi: 10.1016/j.cjsc.2023.100172

    5. [5]

      Muhammad Riaz Rakesh Kumar Gupta Di Sun Mohammad Azam Ping Cui . Selective adsorption of organic dyes and iodine by a two-dimensional cobalt(II) metal-organic framework. Chinese Journal of Structural Chemistry, 2024, 43(12): 100427-100427. doi: 10.1016/j.cjsc.2024.100427

    6. [6]

      Ying-Yu ZhangJia-Qi LuoYan HanWan-Ying ZhangYi ZhangHai-Feng LuDa-Wei Fu . Bistable switch molecule DPACdCl4 showing four physical channels and high phase transition temperature. Chinese Chemical Letters, 2025, 36(1): 109530-. doi: 10.1016/j.cclet.2024.109530

    7. [7]

      Keke HanWenjun RaoXiuli YouHaina ZhangXing YeZhenhong WeiHu Cai . Two new high-temperature molecular ferroelectrics [1,5-3.2.2-Hdabcni]X (X = ClO4, ReO4). Chinese Chemical Letters, 2024, 35(6): 108809-. doi: 10.1016/j.cclet.2023.108809

    8. [8]

      Tiantian LiRuochen JinBin WuDongming LanYunjian MaYonghua Wang . A novel insight of enhancing the hydrogen peroxide tolerance of unspecific peroxygenase from Daldinia caldariorum based on structure. Chinese Chemical Letters, 2024, 35(4): 108701-. doi: 10.1016/j.cclet.2023.108701

    9. [9]

      Shengyu ZhaoQinhao ShiWuliang FengYang LiuXinxin YangXingli ZouXionggang LuYufeng Zhao . Suppression of multistep phase transitions of O3-type cathode for sodium-ion batteries. Chinese Chemical Letters, 2024, 35(5): 108606-. doi: 10.1016/j.cclet.2023.108606

    10. [10]

      Xinyi CaoYucheng JinHailong WangXu DingXiaolin LiuBaoqiu YuXiaoning ZhanJianzhuang Jiang . A tetraaldehyde-derived porous organic cage and covalent organic frameworks: Syntheses, structures, and iodine vapor capture. Chinese Chemical Letters, 2024, 35(9): 109201-. doi: 10.1016/j.cclet.2023.109201

    11. [11]

      Zhexin ChenYuqing ShiFang ZhongKai ZhangFurong ZhangShenghong XieZhongbin ChengQian ZhouYi-You HuangHai-Bin Luo . Discovery of amentoflavone as a natural PDE4 inhibitor with anti-fibrotic effects. Chinese Chemical Letters, 2025, 36(4): 109956-. doi: 10.1016/j.cclet.2024.109956

    12. [12]

      Shengyu ZhaoXuan YuYufeng Zhao . A water-stable high-voltage P3-type cathode for sodium-ion batteries. Chinese Chemical Letters, 2024, 35(9): 109933-. doi: 10.1016/j.cclet.2024.109933

    13. [13]

      Kailong ZhangChao ZhangLuanhui WuQidong YangJiadong ZhangGuang HuLiang SongGaoran LiWenlong Cai . Chloride molten salt derived attapulgite with ground-breaking electrochemical performance. Chinese Chemical Letters, 2024, 35(10): 109618-. doi: 10.1016/j.cclet.2024.109618

    14. [14]

      Mao-Fan LiMing‐Yu GuoDe-Xuan LiuXiao-Xian ChenWei-Jian XuWei-Xiong Zhang . Multi-stimuli responsive behaviors in a new chiral hybrid nitroprusside salt (R-3-hydroxypyrrolidinium)2[Fe(CN)5(NO)]. Chinese Chemical Letters, 2024, 35(12): 109507-. doi: 10.1016/j.cclet.2024.109507

    15. [15]

      Hao-Fei NiJia-He LinGele TeriQiang-Qiang JiaPei-Zhi HuangHai-Feng LuChang-Feng WangZhi-Xu ZhangDa-Wei FuYi Zhang . B-site ion regulation strategy enables performance optimization and multifunctional integration of hybrid perovskite ferroelectrics. Chinese Chemical Letters, 2025, 36(3): 109690-. doi: 10.1016/j.cclet.2024.109690

    16. [16]

      Fan WuShaoyang WuXin YeYurong RenPeng Wei . Research progress of high-entropy cathode materials for sodium-ion batteries. Chinese Chemical Letters, 2025, 36(4): 109851-. doi: 10.1016/j.cclet.2024.109851

    17. [17]

      Jinfeng Chu Lan Jin Yu-Fei Song . Exploration and Practice of Flipped Classroom in Inorganic Chemistry Experiment: a Case Study on the Preparation of Inorganic Crystalline Compounds. University Chemistry, 2024, 39(2): 248-254. doi: 10.3866/PKU.DXHX202308016

    18. [18]

      Yan Liu Yuexiang Zhu Luhua Lai . Introduction to Blended and Small-Class Teaching in Structural Chemistry: Exploring the Structure and Properties of Crystals. University Chemistry, 2024, 39(3): 1-4. doi: 10.3866/PKU.DXHX202306084

    19. [19]

      Junqiao Zhuo Xinchen Huang Qi Wang . Symbol Representation of the Packing-Filling Model of the Crystal Structure and Its Application. University Chemistry, 2024, 39(3): 70-77. doi: 10.3866/PKU.DXHX202311100

    20. [20]

      Yuyao Wang Zhitao Cao Zeyu Du Xinxin Cao Shuquan Liang . Research Progress of Iron-based Polyanionic Cathode Materials for Sodium-Ion Batteries. Acta Physico-Chimica Sinica, 2025, 41(4): 100035-. doi: 10.3866/PKU.WHXB202406014

Metrics
  • PDF Downloads(0)
  • Abstract views(699)
  • HTML views(29)

通讯作者: 陈斌, bchen63@163.com
  • 1. 

    沈阳化工大学材料科学与工程学院 沈阳 110142

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索
Address:Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888
Powered By info@rhhz.net

/

DownLoad:  Full-Size Img  PowerPoint
Return