Citation: DUAN Hai-Chao, YI Ping-Gui, YU Xian-Yong, LI Xiao-Fang, LIU Wu, SU Jian. Synthesis, Crystal Structure and Density Functional Theoretical Study of 1, 3, 5, 7-Tetramethyl-4, 4-difluoro-4-bora-3a, 4a-diaza-s-indacene[J]. Chinese Journal of Inorganic Chemistry, ;2017, 33(12): 2201-2207. doi: 10.11862/CJIC.2017.271 shu

Synthesis, Crystal Structure and Density Functional Theoretical Study of 1, 3, 5, 7-Tetramethyl-4, 4-difluoro-4-bora-3a, 4a-diaza-s-indacene

1.
School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Key Laboratory of Theoretical Organic Chemistry and Functional Molecules of Ministry of Education, Hunan Province College Key Laboratory of QSAR/QSPR, Xiangtan, Hunan 411201, China
2.
School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, China

Corresponding author: YI Ping-Gui, pgyi@hnust.edu.cn
Received Date: 15 May 2017
Revised Date: 11 September 2017

Figures(11)

1, 3, 5, 7-tetramethyl-3a, 4a-diaza-s-indacene p-toluenesulfonate(T1) was synthesized by solvent-free method using 2, 4-dimethylpyrrole, triethyl orthoformate and p-toluenesulfonic acid. 1, 3, 5, 7-tetramethyl-4, 4-difluoro-4-bora-3a, 4a-diaza-s-indacene(F1) was synthesized by solvent-free method using T1, boron trifluoride diethyl ether and triethylamine. The structures of compounds have been characterized by ¹H NMR and single-crystal X-ray diffraction. The results show that T1 belongs to monoclinic system, space group P2₁/c with a=0.777 3(3) nm, b=1.518 5(5)nm, c=1.612 2(5) nm, β=91.923(12)°, V=1.901 9(11) nm³, Z=4 and that F1 belongs to monoclinic system, space group P2₁/n with a=0.775 02(1) nm, b=1.444 20(3) nm, c=1.174 35(2) nm, β=107.779 5(9)°, V=1.251 65(4) nm³, Z=4. In four different solvent, the UV-Vis spectrum of T1, the UV-Vis and steady-state fluorescence spectra of F1 were determined. The possible derived way of T1 and F1 were investigated by the density functional calculation and the front orbital theory.
- 1, 3, 5, 7-tetramethyl-4, 4-difluoro-4-bora-3a, 4a-diaza-s-indacene,
- NMR,
- crystal structure,
- fluorescence spectra,
- density functional theory
1. [1]
  YU Chang-Jiang, JIAO Li-Juan, HAO Er-Hong, et al. China Sciencepaper, 2013, 8(12):1291-1297 doi: 10.3969/j.issn.2095-2783.2013.12.019
2. [2]
  XI Na. Thesis for the Master of Nanjing University of Posts and Telecommunications. 2012.
3. [3]
  KANG Rui-Xue. Thesis for the Master of Henan University. 2015.
4. [4]
  DOU Yuan-Yuan. Thesis for the Master of Henan University. 2013.
5. [5]
  Okada D, Nakamura T, Braam D, et al. ACS Nano, 2016, 10(7):7058-7063 doi: 10.1021/acsnano.6b03188
6. [6]
  Chapran M, Angioni E, Findlay N J, et al. ACS Appl. Mater. Interfaces, 2017, 9(5):4750-4757 doi: 10.1021/acsami.6b13689
7. [7]
  Liu K, Zhao X J, Liu Q X, et al. Sens. Actuators B, 2017, 239:883-889 doi: 10.1016/j.snb.2016.08.109
8. [8]
  Yang P, Zhao J Z, Wu W H, et al. J. Org. Chem., 2012, 77(14):6166-6178 doi: 10.1021/jo300943t
9. [9]
  Gomezduran C F A, Hu R R, Feng G X. et al. ACS Appl. Mater. Interfaces, 2015, 7(28):15168-15176 doi: 10.1021/acsami.5b05033
10. [10]
  Lu J, Ko S B, Walters N R, et al. Org. Lett., 2012, 14(22):5660-5663 doi: 10.1021/ol302633s
11. [11]
  YI Ping-Gui, WANG Tao, YU Xian-Yong, et al. Chinese J. Inorg. Chem., 2011, 27(3):480-486
12. [12]
  Liu G F, Liu J, Sun Z H, et al. Inorg. Chem., 2016, 55(16):8025-8030 doi: 10.1021/acs.inorgchem.6b01143
13. [13]
  Poethig A, Strassner T. Organometallics, 2012, 31(8):3431-3434 doi: 10.1021/om3000345
14. [14]
  HUANG Yan-Ju, NI Liang, WANG Qiang, et al. Chinese J. Inorg. Chem., 2012, 28(5):1050-1054
15. [15]
  Das S, Hung C H, Goswami S. Inorg. Chem., 2003, 42(17):5153-5157 doi: 10.1021/ic030009c
16. [16]
  Altenhoff G, Goddard R, Lehmann C W, et al. J. Am. Chem. Soc., 2004, 126(46):15195-15201 doi: 10.1021/ja045349r
17. [17]
  ZHANG Fu-Xing, WANG Jian-Qiu, KUANG Dai-Zhi, et al. Chinese J. Inorg. Chem., 2013, 29(3):537-543
18. [18]
  Shimizu T, Nakatsu T, Miyairi K, et al. Biochemistry, 2002, 41(21):6651-6659 doi: 10.1021/bi025541a
19. [19]
  Zhou T L, Jia T, Zhao S S, et al. Cryst. Growth Des., 2012, 12(1):179-184 doi: 10.1021/cg200920d
20. [20]
  Zhu Y Q, Guo Y, Xie D Q. J. Phys. Chem. A, 2007, 111(38):9387-9392 doi: 10.1021/jp073939g
21. [21]
  Zade S S, Bendikov M. Org. Lett., 2006, 8(23):5243-5246 doi: 10.1021/ol062030y
22. [22]
  Wang S C, Tantillo D J. J. Phys. Chem. A, 2007, 111(30):7149-7153 doi: 10.1021/jp0724525
23. [23]
  Boyd S L, Boyd R J. J. Chem. Theory Comput., 2007, 3(1):54-61 doi: 10.1021/ct6002912
24. [24]
  Michalkova A, Ilchenko M, Gorb L, et al. J. Phys. Chem. B, 2004, 108(17):5294-5303 doi: 10.1021/jp036766d
25. [25]
  Kovács G, Pápai I. Organometallics, 2006, 25(4):820-825 doi: 10.1021/om050726+
26. [26]
  Gupta M, Silva E F, Svendsen H F. J. Phys. Chem. B, 2012, 116(6):1865-1875 doi: 10.1021/jp2116017
27. [27]
  Caricato M, Scalmani G, Trucks G W, et al. J. Phys. Chem. Lett., 2010, 1(15):2369-2373 doi: 10.1021/jz1007593
28. [28]
  Fang S. Ind. Eng. Chem. Res., 2012, 51(6):2762-2768 doi: 10.1021/ie201475e
29. [29]
  Qu R J, Liu H X, Feng M B, et al. J. Chem. Eng. Data, 2012, 57(9):2442-2455 doi: 10.1021/je300407g
30. [30]
  XU Guang-Xian, LI Le-Min, WANG De-Min. Quantum Chemistry:Vol.2. 2nd Ed. Beijing:Science Press, 2009.
31. [31]
  Ono M, Watanabe H, Kimura H, et al. ACS Chem. Neurosci., 2012, 3(4):319-324 doi: 10.1021/cn3000058
32. [32]
  Fukui K, Translated by LI Rong-Sen. Chemical Reaction and Electronic Orbit. Beijing:Science Press, 1985.
33. [33]
  Belzile M N, Godin R, Durantini A M, et al. J. Am. Chem. Soc., 2016, 138(50):16388-16397 doi: 10.1021/jacs.6b09735
34. [34]
  LUO Liang, LI Wei, GAO Ge, et al. Chem. J. Chinese Universities, 2011, 32(9):2091-2096
1. [1]
  Haitang WANG , Yanni LING , Xiaqing MA , Yuxin CHEN , Rui ZHANG , Keyi WANG , Ying ZHANG , Wenmin WANG . Construction, crystal structures, and biological activities of two Ln^Ⅲ₃ complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1474-1482. doi: 10.11862/CJIC.20240188
2. [2]
  Changqing MIAO , Fengjiao CHEN , Wenyu LI , Shujie WEI , Yuqing YAO , Keyi WANG , Ni WANG , Xiaoyan XIN , Ming FANG . Crystal structures, DNA action, and antibacterial activities of three tetranuclear lanthanide-based complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2455-2465. doi: 10.11862/CJIC.20240192
3. [3]
  Kaifu Zhang , Shan Gao , Bin Yang . Application of Theoretical Calculation with Fun Practice in Raman Spectroscopy Experimental Teaching. University Chemistry, 2025, 40(3): 62-67. doi: 10.12461/PKU.DXHX202404045
4. [4]
  Xinting XIONG , Zhiqiang XIONG , Panlei XIAO , Xuliang NIE , Xiuying SONG , Xiuguang YI . Synthesis, crystal structures, Hirshfeld surface analysis, and antifungal activity of two complexes Na(Ⅰ)/Cd(Ⅱ) assembled by 5-bromo-2-hydroxybenzoic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1661-1670. doi: 10.11862/CJIC.20240145
5. [5]
  Jie ZHAO , Sen LIU , Qikang YIN , Xiaoqing LU , Zhaojie WANG . Theoretical calculation of selective adsorption and separation of CO₂ by alkali metal modified naphthalene/naphthalenediyne. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 515-522. doi: 10.11862/CJIC.20230385
6. [6]
  Jie ZHAO , Huili ZHANG , Xiaoqing LU , Zhaojie WANG . Theoretical calculations of CO₂ capture and separation by functional groups modified 2D covalent organic framework. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 275-283. doi: 10.11862/CJIC.20240213
7. [7]
  Jinkang Jin , Yidian Sheng , Ping Lu , Zhan Lu . Introducing a Website for Learning Nuclear Magnetic Resonance (NMR) Spectrum Analysis. University Chemistry, 2024, 39(11): 388-396. doi: 10.12461/PKU.DXHX202403054
8. [8]
  Hao XU , Ruopeng LI , Peixia YANG , Anmin LIU , Jie BAI . Regulation mechanism of halogen axial coordination atoms on the oxygen reduction activity of Fe-N₄ site: A density functional theory study. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 695-701. doi: 10.11862/CJIC.20240302
9. [9]
  Xin MA , Ya SUN , Na SUN , Qian KANG , Jiajia ZHANG , Ruitao ZHU , Xiaoli GAO . A Tb₂ complex based on polydentate Schiff base: Crystal structure, fluorescence properties, and biological activity. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1347-1356. doi: 10.11862/CJIC.20230357
10. [10]
  Jingjing QING , Fan HE , Zhihui LIU , Shuaipeng HOU , Ya LIU , Yifan JIANG , Mengting TAN , Lifang HE , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two complexes of dimethylglyoxime organotin. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1301-1308. doi: 10.11862/CJIC.20240003
11. [11]
  Xiaoling LUO , Pintian ZOU , Xiaoyan WANG , Zheng LIU , Xiangfei KONG , Qun TANG , Sheng WANG . Synthesis, crystal structures, and properties of lanthanide metal-organic frameworks based on 2, 5-dibromoterephthalic acid ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1143-1150. doi: 10.11862/CJIC.20230271
12. [12]
  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
13. [13]
  Weina Wang , Fengyi Liu , Wenliang Wang . “Extracting Commonality, Delving into Typicals, Deriving Individuality”: Constructing a Knowledge Graph of Crystal Structures. University Chemistry, 2024, 39(3): 36-42. doi: 10.3866/PKU.DXHX202308029
14. [14]
  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
15. [15]
  Jing WU , Puzhen HUI , Huilin ZHENG , Pingchuan YUAN , Chunfei WANG , Hui WANG , Xiaoxia GU . Synthesis, crystal structures, and antitumor activities of transition metal complexes incorporating a naphthol-aldehyde Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2422-2428. doi: 10.11862/CJIC.20240278
16. [16]
  Wenyan Dan , Weijie Li , Xiaogang Wang . The Technical Analysis of Visual Software ShelXle for Refinement of Small Molecular Crystal Structure. University Chemistry, 2024, 39(3): 63-69. doi: 10.3866/PKU.DXHX202302060
17. [17]
  Linjie ZHU , Xufeng LIU . Electrocatalytic hydrogen evolution performance of tetra-iron complexes with bridging diphosphine ligands. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 321-328. doi: 10.11862/CJIC.20240207
18. [18]
  Yongzhi LI , Han ZHANG , Gangding WANG , Yanwei SUI , Lei HOU , Yaoyu WANG . A two-dimensional metal-organic framework for the determination of nitrofurantoin and nitrofurazone in aqueous solution. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 245-253. doi: 10.11862/CJIC.20240307
19. [19]
  Yingchun ZHANG , Yiwei SHI , Ruijie YANG , Xin WANG , Zhiguo SONG , Min WANG . Dual ligands manganese complexes based on benzene sulfonic acid and 2, 2′-bipyridine: Structure and catalytic properties and mechanism in Mannich reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1501-1510. doi: 10.11862/CJIC.20240078
20. [20]
  Xiaochen Zhang , Fei Yu , Jie Ma . 多角度数理模拟在电容去离子中的前沿应用. Acta Physico-Chimica Sinica, 2024, 40(11): 2311026-. doi: 10.3866/PKU.WHXB202311026

Get Citation

PDF

XML

Metrics

PDF Downloads(4)
Abstract views(693)
HTML views(200)

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