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

1.
1 State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing National Laboratory of Microstructures, Nanjing University, Nanjing 210093, China;

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.
- pinene;rhenium(Ⅰ) complex;luminescence;chiral;circular dichlorism
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
1. [1]
  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
2. [2]
  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
3. [3]
  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
4. [4]
  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
5. [5]
  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
6. [6]
  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
7. [7]
  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
8. [8]
  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
9. [9]
  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
10. [10]
  Jin Tong , Shuyan Yu . Crystal Engineering for Supramolecular Chirality. University Chemistry, 2024, 39(3): 86-93. doi: 10.3866/PKU.DXHX202308113
11. [11]
  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
12. [12]
  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
13. [13]
  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
14. [14]
  Renxiao Liang , Zhe Zhong , Zhangling Jin , Lijuan Shi , Yixia Jia . A Palladium/Chiral Phosphoric Acid Relay Catalysis for the One-Pot Three-Step Synthesis of Chiral Tetrahydroquinoline. University Chemistry, 2024, 39(5): 209-217. doi: 10.3866/PKU.DXHX202311024
15. [15]
  Cheng Zheng , Shiying Zheng , Yanping Zhang , Shoutian Zheng , Qiaohua Wei . Synthesis, Copper Content Analysis, and Luminescent Performance Study of Binuclear Copper (I) Complexes with Isomeric Luminescence Shift: A Comprehensive Chemical Experiment Recommendation. University Chemistry, 2024, 39(7): 322-329. doi: 10.3866/PKU.DXHX202310131
16. [16]
  Haiying Wang , Andrew C.-H. Sue . How to Visually Identify Homochiral Crystals. University Chemistry, 2024, 39(3): 78-85. doi: 10.3866/PKU.DXHX202309004
17. [17]
  Keying Qu , Jie Li , Ziqiu Lai , Kai Chen . Unveiling the Mystery of Chirality from Tartaric Acid. University Chemistry, 2024, 39(9): 369-378. doi: 10.12461/PKU.DXHX202310091
18. [18]
  Xian BI , Sisi WANG , Jinyue ZHANG , Yujia PENG , Zhen SHEN , Hua LU . Discovery, development, and perspectives of circularly polarized luminescent materials based on β-isoindigo skeletons. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1049-1057. doi: 10.11862/CJIC.20240456
19. [19]
  Liang TANG , Jingfei NI , Kang XIAO , Xiangmei LIU . Synthesis and X-ray imaging application of lanthanide-organic complex-based scintillators. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1892-1902. doi: 10.11862/CJIC.20240139
20. [20]
  Conghao Shi , Ranran Wang , Juli Jiang , Leyong Wang . The Illustration on Stereoisomers of Macrocycles Containing Multiple Chiral Centers via Tröger Base-based Macrocycles. University Chemistry, 2024, 39(7): 394-397. doi: 10.3866/PKU.DXHX202311034

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(291)
HTML views(21)

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