Citation: Zai-Gang LUO, Qian-Nan LIU, Rui LI, Xue-Mei XU. Synthesis, Crystal Structure and Thermal Property of Dimethyl Phenanthrene-9,10-dicarboxylate[J]. Chinese Journal of Structural Chemistry, ;2020, 39(5): 908-912. doi: 10.14102/j.cnki.0254-5861.2011-2597 shu

Synthesis, Crystal Structure and Thermal Property of Dimethyl Phenanthrene-9,10-dicarboxylate

College of Chemical Engineering, Anhui University of Science and Technology, Huainan 232001, China

Corresponding author: Zai-Gang LUO, luozi139@163.com
Received Date: 10 September 2019
Accepted Date: 18 December 2019

Fund Project: the Natural Science Research Projects in Colleges and Universities of Anhui Province KJ2019A0116Natural Science Foundation of Anhui Province 1608085MB38

Figures(4)

The target compound (C₁₈H₁₄O₄) was synthesized and structurally determined by single-crystal X-ray diffraction. The crystal is of monoclinic system, space group P2₁/n with a = 7.9383(6), b = 19.5083(13), c = 9.4189(7) Å, β = 98.981(2)°, C₁₈H₁₄O₄, M_r = 294.29, D_c = 1.357 g/cm³, V = 1440.75(18) Å³, Z = 4, F(000) = 616, µ(MoKa) = 0.096 mm^-1, T = 293(2) K, 3320 independent reflections with 1845 observed ones (I > 2σ(I)), R = 0.0529 and wR = 0.1082 with GOF = 1.015 (R = 0.1202 and wR = 0.1278 for all data). The phenanthrene skeleton is coplanar. The overall crystal packing revealed that it has reverse staggered parallel and stratified arrangement. And a one-dimensional interaction model was formed by two kinds of π-π interactions between the two adjacent molecules at upper and lower levels. The decomposition mechanism of compound 3 is complex.
- phenanthrene,
- synthesis,
- crystal structure,
- thermal property
1. [1]
  Weil, T. ; Vosch, T. ; Hofkens, J. ; Peneva, K. ; M€ullen, K. The rylene colorant family-tailored nanoemitters for photonics research and applications. Angew. Chem. , Int. Ed. 2010, 49, 9068–9093. doi: 10.1002/anie.200902532
2. [2]
  Avlasevich, Y. ; Li, C. ; M€ullen, K. Synthesis and applications of core-enlarged perylene dyes. J. Mater. Chem. 2010, 20, 3814–3826. doi: 10.1039/c000137f
3. [3]
  Feng, X. ; Pisula, W. ; M€ullen, K. Large polycyclic aromatic hydrocarbons: synthesis and discotic organization. Pure Appl. Chem. 2009, 81, 2203–2224. doi: 10.1351/PAC-CON-09-07-07
4. [4]
  Kaur, I. ; Stein, N. N. ; Kopreski, R. P. ; Miller, G. P. Exploiting substituent effects for the synthesis of a photooxidatively resistant heptacene derivative. J. Am. Chem. Soc. 2009, 131, 3424–3425. doi: 10.1021/ja808881x
5. [5]
  Seri, T. ; Qu, H. ; Zhou, L. ; Kanno, K. I. ; Takahashi, T. Substituent effects in the preparation of naphthacenes by the coupling reaction of diyne-derived zirconacyclopentadienes with tetraiodobenzene. Chem. Asian J. 2008, 3, 388–392. doi: 10.1002/asia.200700376
6. [6]
  Paraskar, A. S. ; Reddy, A. R. ; Patra, A. ; Wijsboom, Y. H. ; Gidron, O. ; Shimon, L. J. W. ; Leitus, G. ; Bendikov, M. Rubrenes: planar and twisted. Chem. Eur. J. 2008, 14, 10639–10647. doi: 10.1002/chem.200800802
7. [7]
  Floyd, A. J. ; Dyke, S. F. ; Ward, S. E. The synthesis of phenanthrenes. Chem. Rev. 1976, 76, 509–562. doi: 10.1021/cr60303a001
8. [8]
  Kotha, S. ; Misra, S. ; Halder, S. Benzannulation. Tetrahedron 2008, 64, 10775–10790. doi: 10.1016/j.tet.2008.09.004
9. [9]
  Wu, G. ; Rheingold, A. L. ; Geib, S. J. ; Heck, R. F. Palladium-catalyzed annelation of aryl iodides with diphenylacetylene. Organometallics 1987, 6, 1941–1946. doi: 10.1021/om00152a019
10. [10]
  Wang, C. ; Rakshit, S. ; Glorius, F. Palladium-catalyzed intermolecular decarboxylative coupling of 2-phenylbenzoic acids with alkynes via C–H and C–C bond activation. J. Am. Chem. Soc. 2010, 132, 14006–14008. doi: 10.1021/ja106130r
11. [11]
  Matsumoto, A. ; Ilies, L. ; Nakamura, E. Phenanthrene synthesis by iron-catalyzed [4+2] benzannulationbetween alkyne and biaryl or 2-alkenylphenyl Grignard reagent. J. Am. Chem. Soc. 2011, 133, 6557–6559. doi: 10.1021/ja201931e
12. [12]
  Nagata, T. ; Hirano, K. ; Satoh, T. ; Miura, M. Iridium-catalyzed annulative coupling of 2‑arylbenzoyl chlorideswith alkynes: selective formation of phenanthrene derivatives. J. Org. Chem. 2014, 79, 8960–8967. doi: 10.1021/jo501835u
13. [13]
  Nagata, T. ; Satoh, T. ; Nishii, Y. ; Miura, M. Rhodium-catalyzed oxidative annulation of (2-arylphenyl)boronic acids with alkynes: selective synthesis of phenanthrene derivatives. Synlett. 2016, 27, 1707–1710. doi: 10.1055/s-0035-1561940
14. [14]
  Hartmann, M. ; Daniliuc, C. G. ; Studer, A. Preparation of phenanthrenes fromortho-amino-biphenyls and alkynesviabase-promoted homolytic aromatic substitution. Chem. Commun. 2015, 51, 3121–3123. doi: 10.1039/C4CC10063H
15. [15]
  Chatterjee, T. ; Lee, D. S. ; Cho, E. J. Extended study of visible-light-induced photocatalytic [4+2] benzannulation: synthesis of polycyclic (hetero)aromatics. J. Org. Chem. 2017, 82, 4369−4378. doi: 10.1021/acs.joc.7b00413
16. [16]
  Jafarpour, F. ; Hazrati, H. ; Nouraldinmousa, S. Three-bond breaking of cyclic anhydrides: easy access to polyfunctionalized naphthalenes and phenanthrenes. Org. Lett. 2013, 17, 3816−3819.
17. [17]
  Sulleiro, M. V. ; Quiroga, S. ; Peña, D. ; Pérez, D. ; Guitián, E. ; Criado, A. ; Prato, M. Microwave-induced covalent functionalization of few-layer graphene with arynes under solvent-free conditions. Chem. Commun. 2018, 54, 2086–2089. doi: 10.1039/C7CC08676H
18. [18]
  Bruker 2000, SMART (Version 5.0), SAINT-plus (Version 6), SHELXTL (Version 6.1), and SADABS (Version 2.03); Bruker AXS Inc. : Madison, WI.
19. [19]
  Sheldrick, G. M. SHELXS-97, Program for X-ray Crystal Structure Solution. University of Göttingen, Germany 1997.
20. [20]
  Sheldrick, G. M. SHELXL-97, Program for the Refinement of Crystal Structure. University of Göttingen: Göttingen, Germany 1997.
21. [21]
  Chen, C. Y. ; Hu, J. S. ; Chai, F. F. ; Xie, K. Y. ; Zhang, X. M. ; Shi, J. J. Synthesis, crystal structure and properties of ethyl 3, 9-dimethyl-7-phenyl-6H-dibenzo[b, d]pyran-6-one-8-carboxylate. Chin. J. Struct. Chem. 2014, 33, 395−400.
1. [1]
  Xiaoling WANG , Hongwu ZHANG , Daofu LIU . Synthesis, structure, and magnetic property of a cobalt(Ⅱ) complex based on pyridyl-substituted imino nitroxide radical. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 407-412. doi: 10.11862/CJIC.20240214
2. [2]
  Yao HUANG , Yingshu WU , Zhichun BAO , Yue HUANG , Shangfeng TANG , Ruixue LIU , Yancheng LIU , Hong LIANG . Copper complexes of anthrahydrazone bearing pyridyl side chain: Synthesis, crystal structure, anticancer activity, and DNA binding. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 213-224. doi: 10.11862/CJIC.20240359
3. [3]
  Lulu DONG , Jie LIU , Hua YANG , Yupei FU , Hongli LIU , Xiaoli CHEN , Huali CUI , Lin LIU , Jijiang WANG . Synthesis, crystal structure, and fluorescence properties of Cd-based complex with pcu topology. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 809-820. doi: 10.11862/CJIC.20240171
4. [4]
  Chao LIU , Jiang WU , Zhaolei JIN . Synthesis, crystal structures, and antibacterial activities of two zinc(Ⅱ) complexes bearing 5-phenyl-1H-pyrazole group. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1986-1994. doi: 10.11862/CJIC.20240153
5. [5]
  Xiaoxia WANG , Ya'nan GUO , Feng SU , Chun HAN , Long SUN . Synthesis, structure, and electrocatalytic oxygen reduction reaction properties of metal antimony-based chalcogenide clusters. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1201-1208. doi: 10.11862/CJIC.20230478
6. [6]
  Kaimin WANG , Xiong GU , Na DENG , Hongmei YU , Yanqin YE , Yulu MA . Synthesis, structure, fluorescence properties, and Hirshfeld surface analysis of three Zn(Ⅱ)/Cu(Ⅱ) complexes based on 5-(dimethylamino) isophthalic acid. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1397-1408. doi: 10.11862/CJIC.20240009
7. [7]
  Jia JI , Zhaoyang GUO , Wenni LEI , Jiawei ZHENG , Haorong QIN , Jiahong YAN , Yinling HOU , Xiaoyan XIN , Wenmin WANG . Two dinuclear Gd(Ⅲ)-based complexes constructed by a multidentate diacylhydrazone ligand: Crystal structure, magnetocaloric effect, and biological activity. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 761-772. doi: 10.11862/CJIC.20240344
8. [8]
  Ruikui YAN , Xiaoli CHEN , Miao CAI , Jing REN , Huali CUI , Hua YANG , Jijiang WANG . Design, synthesis, and fluorescence sensing performance of highly sensitive and multi-response lanthanide metal-organic frameworks. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 834-848. doi: 10.11862/CJIC.20230301
9. [9]
  Lu LIU , Huijie WANG , Haitong WANG , Ying LI . Crystal structure of a two-dimensional Cd(Ⅱ) complex and its fluorescence recognition of p-nitrophenol, tetracycline, 2, 6-dichloro-4-nitroaniline. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1180-1188. doi: 10.11862/CJIC.20230489
10. [10]
  Xiumei LI , Yanju HUANG , Bo LIU , Yaru PAN . Syntheses, crystal structures, and quantum chemistry calculation of two Ni(Ⅱ) coordination polymers. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 2031-2039. doi: 10.11862/CJIC.20240109
11. [11]
  Xiumei LI , Linlin LI , Bo LIU , Yaru PAN . Syntheses, crystal structures, and characterizations of two cadmium(Ⅱ) coordination polymers. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 613-623. doi: 10.11862/CJIC.20240273
12. [12]
  Yan XU , Suzhi LI , Yan LI , Lushun FENG , Wentao SUN , Xinxing LI . Structure variation of cadmium naphthalene-diphosphonates with the changing rigidity of N-donor auxiliary ligands. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 395-406. doi: 10.11862/CJIC.20240226
13. [13]
  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
14. [14]
  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
15. [15]
  Huan ZHANG , Jijiang WANG , Guang FAN , Long TANG , Erlin YUE , Chao BAI , Xiao WANG , Yuqi ZHANG . A highly stable cadmium(Ⅱ) metal-organic framework for detecting tetracycline and p-nitrophenol. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 646-654. doi: 10.11862/CJIC.20230291
16. [16]
  Meirong HAN , Xiaoyang WEI , Sisi FENG , Yuting BAI . A zinc-based metal-organic framework for fluorescence detection of trace Cu²⁺. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1603-1614. doi: 10.11862/CJIC.20240150
17. [17]
  Shuyan ZHAO . Field-induced Co^Ⅱ single-ion magnet with pentagonal bipyramidal configuration. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1583-1591. doi: 10.11862/CJIC.20240231
18. [18]
  Yinling HOU , Jia JI , Hong YU , Xiaoyun BIAN , Xiaofen GUAN , Jing QIU , Shuyi REN , Ming FANG . A rhombic Dy₄-based complex showing remarkable single-molecule magnet behavior. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 605-612. doi: 10.11862/CJIC.20240251
19. [19]
  Xiaofen GUAN , Yating LIU , Jia LI , Yiwen HU , Haiyuan DING , Yuanjing SHI , Zhiqiang WANG , Wenmin WANG . Synthesis, crystal structure, and DNA-binding of binuclear lanthanide complexes based on a multidentate Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2486-2496. doi: 10.11862/CJIC.20240122
20. [20]
  Zhaodong WANG . In situ synthesis, crystal structure, and magnetic characterization of a trinuclear copper complex based on a multi-substituted imidazo[1,5-a]pyrazine scaffold. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 597-604. doi: 10.11862/CJIC.20240268

Get Citation

PDF

XML

Metrics

PDF Downloads(2)
Abstract views(393)
HTML views(6)

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