Citation: LI Shu-Jing, ZHANG Xiao-Peng, LIU Jian, ZHENG Wei, LI Cheng-Hui. Synthesis and Characterization of Chiral 2,5-Bis(4,5-pinene-2-pyridyl) Pyrazine and Its Rhenium(Ⅰ) Complex[J]. Chinese Journal of Inorganic Chemistry, ;2013, 29(8): 1745-1752. doi: 10.3969/j.issn.1001-4861.2013.00.295 shu

Synthesis and Characterization of Chiral 2,5-Bis(4,5-pinene-2-pyridyl) Pyrazine and Its Rhenium(Ⅰ) Complex

  • Received Date: 31 January 2013
    Available Online: 25 May 2013

    Fund Project: 国家自然科学基金(No.21001063,91022031) (No.21001063,91022031)河南省科技厅科技攻关(No.122102210250)资助项目。 (No.122102210250)

  • The chiral ligand 2,5-bis(4,5-pinene-2-pyridyl) pyrazine (L) and its rhenium(Ⅰ) complex [Re(CO)3Cl(L)]·DMF were synthesized. X-ray crystallographic analysis show that L crystallizes in monoclinic P21 space group while [Re(CO)3Cl(L)]·DMF crystallizes in orthorhombic P212121 space group. The Re(Ⅰ) atom is six-coordinated by two nitrogen atoms (N1, N2) from the chiral ligand, three carbon atoms (C1, C2 and C3) from CO, and one chlorine atom (Cl1). Both ligand and [Re(CO)3Cl(L)]·DMF show optical activity as manifested by the CD and VCD spectra. Upon excitation, the ligand and Re(Ⅰ) complex emit at 420 and 650 nm, respectively. Both the ligand and Re(Ⅰ) complex show second-order non-linear optic (NLO) properties, and the second harmonic generation (SHG) responses are ~0.4 and ~0.3 times that of urea, respectively. CCDC: 921976, complex; 921977, ligand.
  • 加载中
    1. [1]

      [1] Amouri H, Gruselle M. Chirality in Transition Metal Chemistry: Molecules, Supramolecular Assemblies and Materials. Chich-ester: John Wiley & Sons, 2008.

    2. [2]

      [2] von Zelewsky A. Stereochemistry of Coordination Compounds. Chichester: John Wiley & Sons, 1996.

    3. [3]

      [3] Liu J, Zhang X P, Wu T, et al. Inorg. Chem., 2012,51:8649-8651

    4. [4]

      [4] Zhang J, Gao S, Zhang X X, et al. Dalton Trans., 2012,41: 2626-2631

    5. [5]

      [5] Mutti F G, Zoppellaro G, Gullotti M, et al. Eur. J. Inorg. Chem., 2009,4:554-566

    6. [6]

      [6] Mejia E, Aardoom R, Togni A. Eur. J. Inorg. Chem., 2012, 31:5021-5032

    7. [7]

      [7] Chen Q, Zhou J, Han Q, et al. J. Solid State Electrochem., 2012,16:2481-2485

    8. [8]

      [8] Gong L, Mulcahy S P, Harms K, et al. J. Am. Chem. Soc., 2009,131:9602-9603

    9. [9]

      [9] Pradeep C P, Zacharias P S, Das S K. Eur. J. Inorg. Chem., 2007,34:5377-5389

    10. [10]

      [10] Hamann C, von Zelewsky A, Neels A, et al. Dalton Trans., 2004,3:402-406

    11. [11]

      [11] Knof U, von Zelewsky A. Angew. Chem. Int. Ed., 1999,38: 302-322

    12. [12]

      [12] Bark T, Stoeckli-Evans H, von Zelewsky A. J. Chem. Soc. Perkin Trans., 2002,16:1881-1886

    13. [13]

      [13] Malkov A V, Stewart-Liddon A J P, Teply F, et al. Tetrahedron, 2008,64:4011-4025

    14. [14]

      [14] Malkov A V, Bella M, Langer V, et al. Org. Lett., 2000,2: 3047-3049

    15. [15]

      [15] Rich J, Rodriguez M, Romero I, et al. Dalton Trans., 2009, 38:8117-8126

    16. [16]

      [16] Mamula O, Lama M, Telfer S G, et al. Angew. Chem. Int. Ed., 2005,44:2527-2531

    17. [17]

      [17] Yi X Y, Zhao J Z, Wu W H, et al. Dalton Trans., 2012,41: 8931-8940

    18. [18]

      [18] Oriskovich T A, White P S, Thorp H H. Inorg. Chem., 1995, 34:1629-1631

    19. [19]

      [19] Esteves T, Xavier C, Gama S, et al. Org. Biomol. Chem., 2010,8:4104-4116

    20. [20]

      [20] Yeung H L, Wong W Y, Wong C Y, et al. Inorg. Chem., 2009,48:4108-4117

    21. [21]

      [21] SAINT, Area Detector Control and Integration Software, Siemens Analytiacl X-ray instruments Inc., Madison, WI, USA, 1996.

    22. [22]

      [22] Sheldrick G M. SHELXTL-97, Program for Refinement of Crystal Structures, University of Göttingen, Germany, 1997.

    23. [23]

      [23] Wu T, Li C H, Li Y Z, et al. Dalton Trans., 2010,39:3227-3232

    24. [24]

      [24] Wu T, Zhang X P, Li C H, et al. Chirality, 2012,24:451-458

    25. [25]

      [25] Kurtz S K, Perry T T. J. Appl. Phys., 1968,39:3798-3813

    26. [26]

      [26] Lama M, Mamula O, Kottas G S, et al. Inorg. Chem., 2008, 47:8000-8015

    27. [27]

      [27] Uddin M J, Dicesare N, Lakowicz J R. Inorg. Chim. Acta, 2012,381:104-110

    28. [28]

      [28] Waterland M R, Simpson T J, Gordon K C, et al. J. Chem. Soc., Dalton Trans., 1998,1:185-192

    29. [29]

      [29] Li X, Zhang D Y, Lu G H, et al. J. Photochem. Photobio. A, 2012,214:1-7

    30. [30]

      [30] Li D P, Li C H, Wang J, et al. Eur. J. Inorg. Chem., 2009, 32:4844-4849

  • 加载中
    1. [1]

      Qi Liang ,  Xinxin Wang ,  Xinmiao Zhao ,  Mohan Yu ,  Yue Sun . 电子圆二色谱结合量子化学计算的氨基酸手性解析——介绍一个计算化学综合实验. University Chemistry, 2026, 41(5): 380-390. doi: 10.12461/PKU.DXHX202511096

    2. [2]

      Guilan He ,  Yaofeng Yuan . 手性二茂铁双膦配体Xyliphos的合成及应用. University Chemistry, 2025, 40(8): 130-137. doi: 10.12461/PKU.DXHX202409122

    3. [3]

      Ke QIAO , Yanlin LI , Shengli HUANG , Guoyu YANG . Advancements in asymmetric catalysis employing chiral iridium (ruthenium) complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2091-2104. doi: 10.11862/CJIC.20240265

    4. [4]

      Wenjuan SHI , Yuxuan LEI , Lei HOU , Yaoyu WANG . Synthesis, structure, and luminescence properties of trinucluear Cu(Ⅰ)-pyrazole complexes containing different substituent groups. Chinese Journal of Inorganic Chemistry, 2026, 42(3): 543-550. doi: 10.11862/CJIC.20250270

    5. [5]

      Dongheng WANG , Si LI , Shuangquan ZANG . Construction of chiral alkynyl silver chains and modulation of chiral optical properties. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 131-140. doi: 10.11862/CJIC.20240379

    6. [6]

      Yi DING , Peiyu LIAO , Jianhua JIA , Mingliang TONG . Structure and photoluminescence modulation of silver(Ⅰ)-tetra(pyridin-4-yl)ethene metal-organic frameworks by substituted benzoates. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 141-148. doi: 10.11862/CJIC.20240393

    7. [7]

      Tong WANG , Xuefang ZHU , Qi GAO , Hongbo ZHANG , Chao REN , Lixia GE . Luminescence and thermal stability of Tb3+-Eu3+ doped glass-ceramics containing Na8.12Y1.293Si6O18 crystal phase. Chinese Journal of Inorganic Chemistry, 2025, 41(11): 2237-2250. doi: 10.11862/CJIC.20250137

    8. [8]

      Qiuting Zhang ,  Fan Wu ,  Jin Liu ,  Zian Lin . Chromatographic Stationary Phase and Chiral Separation Using Frame Materials. University Chemistry, 2025, 40(4): 291-298. doi: 10.12461/PKU.DXHX202405174

    9. [9]

      Xilin Zhao ,  Xingyu Tu ,  Zongxuan Li ,  Rui Dong ,  Bo Jiang ,  Zhiwei Miao . Research Progress in Enantioselective Synthesis of Axial Chiral Compounds. University Chemistry, 2024, 39(11): 158-173. doi: 10.12461/PKU.DXHX202403106

    10. [10]

      Ruiying WANG , Hui WANG , Fenglan CHAI , Zhinan ZUO , Benlai WU . Three-dimensional homochiral Eu(Ⅲ) coordination polymer and its amino acid configuration recognition. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 877-884. doi: 10.11862/CJIC.20250052

    11. [11]

      Tingyu Zhu ,  Hui Zhang ,  Wenwei Zhang . Exploration and Practice of Ideological and Political Education in the Course of Experiments on Chemical Functional Molecules: Synthesis and Catalytic Performance Study of Chiral Mn(III)Cl-Salen Complex. University Chemistry, 2024, 39(4): 75-80. doi: 10.3866/PKU.DXHX202311011

    12. [12]

      Huahong ZHANG , Yang ZHAO , Rui NING , Shuixing WU , Xiaopeng ZHANG . Coordination equilibrium between cyclometalated Pt(Ⅱ) complexs [Pt(κ3-N^C^N′)(CNXyl)]Cl and [Pt(κ2-N^C^N′)(CNXyl)Cl]. Chinese Journal of Inorganic Chemistry, 2025, 41(9): 1840-1850. doi: 10.11862/CJIC.20250136

    13. [13]

      Tianyun Chen ,  Ruilin Xiao ,  Xinsheng Gu ,  Yunyi Shao ,  Qiujun Lu . Synthesis, Crystal Structure, and Mechanoluminescence Properties of Lanthanide-Based Organometallic Complexes. University Chemistry, 2024, 39(5): 363-370. doi: 10.3866/PKU.DXHX202312017

    14. [14]

      Jin Tong ,  Shuyan Yu . Crystal Engineering for Supramolecular Chirality. University Chemistry, 2024, 39(3): 86-93. doi: 10.3866/PKU.DXHX202308113

    15. [15]

      Runjie Li ,  Hang Liu ,  Xisheng Wang ,  Wanqun Zhang ,  Wanqun Hu ,  Kaiping Yang ,  Qiang Zhou ,  Si Liu ,  Pingping Zhu ,  Wei Shao . 氨基酸的衍生及手性气相色谱分离创新实验. University Chemistry, 2025, 40(6): 286-295. doi: 10.12461/PKU.DXHX202407059

    16. [16]

      Wenkai Chen ,  Yunjia Shen ,  Xiangmeng Kong ,  Yanli Zeng . Quantum Chemistry Calculation of Key Physical Quantity in Circularly Polarized Luminescence: Introducing an Exploratory Computational Chemistry Experiment. University Chemistry, 2025, 40(3): 83-91. doi: 10.12461/PKU.DXHX202405018

    17. [17]

      Cun WANG , Shaohan XU , Yuqian ZHANG , Yaoyao ZHANG , Tao GONG , Rong WEN , Yuhang LIAO , Yanrong REN . Terbium complex electrochemiluminescent emitters: Synthesis and application in the detection of epinephrine. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1351-1360. doi: 10.11862/CJIC.20240427

    18. [18]

      Xuyu WANG , Xinran XIE , Dengke CAO . Photoreaction characteristics and luminescence modulation in phosphine-anthracene-based Au(Ⅰ) and Ir(Ⅲ) complexes. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1513-1522. doi: 10.11862/CJIC.20250113

    19. [19]

      Ting WANG , Peipei ZHANG , Shuqin LIU , Ruihong WANG , Jianjun ZHANG . A Bi-CP-based solid-state thin-film sensor: Preparation and luminescence sensing for bioamine vapors. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1615-1621. doi: 10.11862/CJIC.20240134

    20. [20]

      Huaihao CHEN , Lingwen ZHANG , Yukun CHEN , Jianjun ZHANG . A water-stable metal-organic framework probe for Al3+/Ga3+/In3+ detection. Chinese Journal of Inorganic Chemistry, 2025, 41(12): 2601-2608. doi: 10.11862/CJIC.20250184

Metrics
  • PDF Downloads(0)
  • Abstract views(873)
  • HTML views(49)

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