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

被引:0
作者
Luo Zai-Gang [1 ]
Liu Qian-Nan [1 ]
Li Rui [1 ]
Xu Xue-Mei [1 ]
机构
[1] Anhui Univ Sci & Technol, Coll Chem Engn, Huainan 232001, Peoples R China
关键词
phenanthrene; synthesis; crystal structure; thermal property; 4+2 BENZANNULATION; ALKYNES; ACIDS;
D O I
10.14102/j.cnki.0254-5861.2011-2597
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The target compound (C18H14O4) was synthesized and structurally determined by single-crystal X-ray diffraction. The crystal is of monoclinic system, space group P2(1)/n with a = 7.9383(6), b = 19.5083(13), c = 9.4189(7) angstrom, beta = 98.981(2)degrees, C18H14O4, M-r = 294.29, D-c = 1.357 g/cm(3), V = 1440.75(18) angstrom(3), Z = 4, F(000) = 616, mu(MoKa) = 0.096 mm(-1), T = 293(2) K, 3320 independent reflections with 1845 observed ones (I > 2 sigma(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 pi-pi interactions between the two adjacent molecules at upper and lower levels. The decomposition mechanism of compound 3 is complex.
引用
收藏
页码:908 / 912
页数:5
相关论文
共 21 条
[11]   Phenanthrene Synthesis by Iron-Catalyzed [4+2] Benzannulation between Alkyne and Biaryl or 2-Alkenylphenyl Grignard Reagent [J].
Matsumoto, Arimasa ;
Ilies, Laurean ;
Nakamura, Eiichi .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (17) :6557-6559
[12]   Rhodium-Catalyzed Oxidative Annulation of (2-Arylphenyl)boronic Acids with Alkynes: Selective Synthesis of Phenanthrene Derivatives [J].
Nagata, Tomoya ;
Satoh, Tetsuya ;
Nishii, Yuji ;
Miura, Masahiro .
SYNLETT, 2016, 27 (11) :1707-1710
[13]   Iridium-Catalyzed Annulative Coupling of 2-Arylbenzoyl Chlorides with Alkynes: Selective Formation of Phenanthrene Derivatives [J].
Nagata, Tomoya ;
Hirano, Koji ;
Satoh, Tetsuya ;
Miura, Masahiro .
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (19) :8960-8967
[14]   Rubrenes: Planar and Twisted [J].
Paraskar, Abhimanyu S. ;
Reddy, A. Ravikumar ;
Patra, Asit ;
Wjjsboom, Yair H. ;
Gidron, Ori ;
Shimon, Linda J. W. ;
Leitus, Gregory ;
Bendikov, Michael .
CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (34) :10639-10647
[15]   Substituent effects in the preparation of naphthacenes by the coupling reaction of diyne-derived zirconacyclopentadienes with tetraiodobenzene [J].
Seri, Tomomi ;
Qu, Hongmei ;
Zhou, Lishan ;
Kanno, Ken-ichiro ;
Takahashi, Tamotsu .
CHEMISTRY-AN ASIAN JOURNAL, 2008, 3 (02) :388-392
[16]   SHELXT - Integrated space-group and crystal-structure determination [J].
Sheldrick, George M. .
ACTA CRYSTALLOGRAPHICA A-FOUNDATION AND ADVANCES, 2015, 71 :3-8
[17]  
Sheldrick G.M., 1993, PROGRAM CRYSTAL STRU
[18]   Microwave-induced covalent functionalization of few-layer graphene with arynes under solvent-free conditions [J].
Sulleiro, M. V. ;
Quiroga, S. ;
Pena, D. ;
Perez, D. ;
Guitian, E. ;
Criado, A. ;
Prato, M. .
CHEMICAL COMMUNICATIONS, 2018, 54 (17) :2086-2089
[19]   Palladium-Catalyzed Intermolecular Decarboxylative Coupling of 2-Phenylbenzoic Acids with Alkynes via C-H and C-C Bond Activation [J].
Wang, Congyang ;
Rakshit, Souvik ;
Glorius, Frank .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (40) :14006-14008
[20]   The Rylene Colorant Family-Tailored Nanoemitters for Photonics Research and Applications [J].
Weil, Tanja ;
Vosch, Tom ;
Hofkens, Johan ;
Peneva, Kalina ;
Muellen, Klaus .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (48) :9068-9093