fbpx
维基百科

碗烯

二月 05, 2023

碗烯（英語：Corannulene），又稱心環烯，是一种多环芳香烃，化学式為C20H10，[1]由一个环戊烷周围并五个苯环组成，它具有碗状的空间结构，可看做是富勒烯C60的一个片段。在−64℃时，碗状结构翻转的能垒是42.7kJ/mol（10.2 kcal/mol）。[2]

碗烯
IUPAC名
Dibenzo[ghi,mno]fluoranthene
二苯并[ghi,mno]熒蒽
别名 心環烯
[5]環烯
识别
CAS号 5821-51-2  
PubChem 11831840
ChemSpider 10006487
SMILES
InChI
InChIKey VXRUJZQPKRBJKH-UHFFFAOYAF
性质
化学式 C20H10
摩尔质量 250.29 g/mol g·mol⁻¹
若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

合成

通过快速真空裂解技术得到的碗烯纯度比溶液法低，但同时能得到各种碗烯衍生物。
1966年，碗烯首次由多步有机合成并从产物中分离出来。[3][4][5]由[[荧]蒽]的溴代衍生物在碱催化下通过分子内的亲核取代关环得四溴代的碗烯：

 

再由过量的正丁基锂通过卤素－锂交换除溴，经水解得到碗烯。

有合成含不同官能团的碗烯衍生物的研究，例如含乙炔基、[2][6][7]醚键、[8]硫醚、[9]含铂官能团、[10]芳基、[11]萉[12]和茚的并环[13][14]的碗烯衍生物。

芳香性

一种解释碗烯芳香性的模型将碗烯分成中间6电子和外围14电子的两个芳香性的共轭体系。这个模型由1966年首次合成碗烯的巴特和劳顿提出，[3]他们还给出了这个化合物的命名建议（corannulene意为核+轮烯）。

 

然而，之后理论计算的结果并不支持这种模型。[15][16]

应用

 
“球碳捕手”

碗烯被用于主客体化学的研究，例如碗烯基团与富勒烯[17][18]和硝基苯之间的π重叠。[19]

长脂肪烃基侧链取代碗烯存在热致变的六角形柱状液晶的中间相。[20]碗烯基团也被用于树形高分子的组装，[11]或研究其作为配体的性质。[21][22][23][24][25][26][27]乙炔基碗烯衍生物对于制造蓝光发射器有潜在的应用价值。[7]

参见

参考文献

  1. ^ Scott, L. T.; Bronstein, H. E.; Preda, D. V.; Ansems, R. B. M.; Bratcher, M. S.; Hagen, Stefan. Geodesic polyarenes with exposed concave surfaces. Pure and Applied Chemistry (Walter de Gruyter GmbH). 1999-01-28, 71 (2). ISSN 1365-3075. doi:10.1351/pac199971020209. 
  2. ^ 2.0 2.1 Scott, Lawrence T.; Hashemi, Mohammed M.; Bratcher, Matthew S. Corannulene bowl-to-bowl inversion is rapid at room temperature. Journal of the American Chemical Society (American Chemical Society (ACS)). 1992, 114 (5): 1920–1921. ISSN 0002-7863. doi:10.1021/ja00031a079. 
  3. ^ 3.0 3.1 Barth, Wayne E.; Lawton, Richard G. Dibenzo[ghi,mno]fluoranthene. Journal of the American Chemical Society (American Chemical Society (ACS)). 1966, 88 (2): 380–381. ISSN 0002-7863. doi:10.1021/ja00954a049. 
  4. ^ Scott, Lawrence T.; Hashemi, Mohammed M.; Meyer, Dayton T.; Warren, Hope B. Corannulene. A convenient new synthesis. Journal of the American Chemical Society (American Chemical Society (ACS)). 1991, 113 (18): 7082–7084. ISSN 0002-7863. doi:10.1021/ja00018a082. 
  5. ^ Sygula, Andrzej; Rabideau, Peter W. A Practical, Large Scale Synthesis of the Corannulene System. Journal of the American Chemical Society (American Chemical Society (ACS)). 2000, 122 (26): 6323–6324. ISSN 0002-7863. doi:10.1021/ja0011461. 
  6. ^ Wu, Yao-Ting; Bandera, Davide; Maag, Roman; Linden, Anthony; Baldridge, Kim K.; Siegel, Jay S. Multiethynyl Corannulenes: Synthesis, Structure, and Properties. Journal of the American Chemical Society (American Chemical Society (ACS)). 2008, 130 (32): 10729–10739. ISSN 0002-7863. doi:10.1021/ja802334n. 
  7. ^ 7.0 7.1 Mack, James; Vogel, Philip; Jones, Derek; Kaval, Necati; Sutton, Art. The development of corannulene-based blue emitters. Organic & Biomolecular Chemistry (Royal Society of Chemistry (RSC)). 2007, 5 (15): 2448. ISSN 1477-0520. doi:10.1039/b705621d. 
  8. ^ Gershoni-Poranne, Renana; Pappo, Doron; Solel, Ephrath; Keinan, Ehud. Corannulene Ethers via Ullmann Condensation. Organic Letters (American Chemical Society (ACS)). 2009-11-19, 11 (22): 5146–5149. ISSN 1523-7060. doi:10.1021/ol902352k. 
  9. ^ Baldridge, Kim K.; Hardcastle, Kenneth I.; Seiders, T. Jon; Siegel, Jay S. Synthesis, structure and properties of decakis(phenylthio)corannulene. Org. Biomol. Chem. (Royal Society of Chemistry (RSC)). 2010, 8 (1): 53–55. ISSN 1477-0520. doi:10.1039/b919616a. 
  10. ^ Choi, Hyunbong; Kim, Chulwoo; Park, Ki-Min; Kim, Jinho; Kang, Youngjin; Ko, Jaejung. Synthesis and structure of penta-platinum σ-bonded derivatives of corannulene. Journal of Organometallic Chemistry (Elsevier BV). 2009, 694 (22): 3529–3532. ISSN 0022-328X. doi:10.1016/j.jorganchem.2009.07.015. 
  11. ^ 11.0 11.1 Pappo, Doron; Mejuch, Tom; Reany, Ofer; Solel, Ephrath; Gurram, Mahender; Keinan, Ehud. Diverse Functionalization of Corannulene: Easy Access to Pentagonal Superstructure. Organic Letters (American Chemical Society (ACS)). 2009-03-05, 11 (5): 1063–1066. ISSN 1523-7060. doi:10.1021/ol8028127. 
  12. ^ Nishida, Shinsuke; Morita, Yasushi; Ueda, Akira; Kobayashi, Tadahiro; Fukui, Kozo; Ogasawara, Kanako; Sato, Kazunobu; Takui, Takeji; Nakasuji, Kazuhiro. Curve-Structured Phenalenyl Chemistry: Synthesis, Electronic Structure, and Bowl-Inversion Barrier of a Phenalenyl-Fused Corannulene Anion. Journal of the American Chemical Society (American Chemical Society (ACS)). 2008-11-12, 130 (45): 14954–14955. ISSN 0002-7863. doi:10.1021/ja806708j. 
  13. ^ Steinberg, Brian D.; Jackson, Edward A.; Filatov, Alexander S.; Wakamiya, Atsushi; Petrukhina, Marina A.; Scott, Lawrence T. Aromatic π-Systems More Curved Than C60. The Complete Family of All Indenocorannulenes Synthesized by Iterative Microwave-Assisted Intramolecular Arylations. Journal of the American Chemical Society (American Chemical Society (ACS)). 2009-08-05, 131 (30): 10537–10545. ISSN 0002-7863. doi:10.1021/ja9031852. 
  14. ^ Corannulenylferrocenes: towards a 1D, non-covalent metal–organic nanowire Berit Topolinski , Bernd M. Schmidt , Michael Kathan , Sergej I. Troyanov and Dieter Lentz Chem. Commun., 2012,48, 6298-6300 doi:10.1039/C2CC32275G
  15. ^ Sygula, Andrzej; Rabideau, Peter W. Structure and inversion barriers of corannulene, its dianion and tetraanion. An ab initio study. Journal of Molecular Structure: THEOCHEM (Elsevier BV). 1995, 333 (3): 215–226. ISSN 0166-1280. doi:10.1016/0166-1280(94)03961-j. 
  16. ^ Monaco, Guglielmo; Scott, Lawrence T.; Zanasi, Riccardo. Magnetic Euripi in Corannulene. The Journal of Physical Chemistry A (American Chemical Society (ACS)). 2008-09-04, 112 (35): 8136–8147. ISSN 1089-5639. doi:10.1021/jp8038779. 
  17. ^ Sygula, Andrzej; Fronczek, Frank R.; Sygula, Renata; Rabideau, Peter W.; Olmstead, Marilyn M. A Double Concave Hydrocarbon Buckycatcher. Journal of the American Chemical Society (American Chemical Society (ACS)). 2007, 129 (13): 3842–3843. ISSN 0002-7863. doi:10.1021/ja070616p. 
  18. ^ Wong, Bryan M. Noncovalent interactions in supramolecular complexes: A study on corannulene and the double concave buckycatcher. Journal of Computational Chemistry (Wiley-Blackwell). 2009-01-15, 30 (1): 51–56. ISSN 0192-8651. doi:10.1002/jcc.21022. 
  19. ^ Kobryn, Lesya; Henry, William P.; Fronczek, Frank R.; Sygula, Renata; Sygula, Andrzej. Molecular clips and tweezers with corannulene pincers. Tetrahedron Letters (Elsevier BV). 2009, 50 (51): 7124–7127. ISSN 0040-4039. doi:10.1016/j.tetlet.2009.09.177. 
  20. ^ Miyajima, Daigo; Tashiro, Kentaro; Araoka, Fumito; Takezoe, Hideo; Kim, Jungeun; Kato, Kenichi; Takata, Masaki; Aida, Takuzo. Liquid Crystalline Corannulene Responsive to Electric Field. Journal of the American Chemical Society (American Chemical Society (ACS)). 2009-01-14, 131 (1): 44–45. ISSN 0002-7863. doi:10.1021/ja808396b. 
  21. ^ Hexahapto Metal Coordination to Curved Polyaromatic Hydrocarbon Surfaces: The First Transition Metal Corannulene Complex T. Jon Seiders, Kim K. Baldridge, Joseph M. O'Connor, and Jay S. Siegel J. Am. Chem. Soc., 1997, 119 (20), pp 4781–4782 doi:10.1021/ja964380t
  22. ^ d8 Rhodium and Iridium Complexes of Corannulene Jay S. Siegel, Kim K. Baldridge, Anthony Linden, and Reto Dorta J. Am. Chem. Soc., 2006, 128 (33), pp 10644–10645 doi:10.1021/ja062110x
  23. ^ Petrukhina, Marina A. Coordination of Buckybowls: The First Concave-Bound Metal Complex. Angewandte Chemie International Edition (Wiley-Blackwell). 2008-02-15, 47 (9): 1550–1552. ISSN 1433-7851. doi:10.1002/anie.200704783. 
  24. ^ Zhu, Bolin; Ellern, Arkady; Sygula, Andrzej; Sygula, Renata; Angelici, Robert J. η6-Coordination of the Curved Carbon Surface of Corannulene (C20H10) to (η6-arene)M2+(M = Ru, Os). Organometallics (American Chemical Society (ACS)). 2007, 26 (7): 1721–1728. ISSN 0276-7333. doi:10.1021/om0610795. 
  25. ^ Petrukhina, Marina A.; Sevryugina, Yulia; Rogachev, Andrey Yu.; Jackson, Edward A.; Scott, Lawrence T. Corannulene: A Preference forexo-Metal Binding. X-ray Structural Characterization of [Ru2(O2CCF3)2(CO)4·(η2-C20H10)2]. Organometallics (American Chemical Society (ACS)). 2006, 25 (22): 5492–5495. ISSN 0276-7333. doi:10.1021/om060350f. 
  26. ^ Siegel, Jay S.; Baldridge, Kim K.; Linden, Anthony; Dorta, Reto. d8Rhodium and Iridium Complexes of Corannulene. Journal of the American Chemical Society (American Chemical Society (ACS)). 2006, 128 (33): 10644–10645. ISSN 0002-7863. doi:10.1021/ja062110x. 
  27. ^ Bandera, D., Baldridge, K. K., Linden, A., Dorta, R. and Siegel, J. S. (2011), Stereoselective Coordination of C5-Symmetric Corannulene Derivatives with an Enantiomerically Pure [RhI(nbd*)] Metal Complex. Angewandte Chemie International Edition, 50: 865–867. doi:10.1002/anie.201006877


二月 05, 2023
碗烯, 英語, corannulene, 又稱心環烯, 是一种多环芳香烃, 化学式為c20h10, 由一个环戊烷周围并五个苯环组成, 它具有碗状的空间结构, 可看做是富勒烯c60的一个片段, 碗状结构翻转的能垒是42, kcal, iupac名dibenzo, fluoranthene二苯并, 熒蒽别名, 心環烯, 環烯识别cas号, 5821, pubchem, 11831840chemspider, 10006487smiles, c16ccc2ccc3ccc5c4c, c1c2c34, cc6inchi, c. 碗烯 英語 Corannulene 又稱心環烯 是一种多环芳香烃 化学式為C20H10 1 由一个环戊烷周围并五个苯环组成 它具有碗状的空间结构 可看做是富勒烯C60的一个片段 在 64 时 碗状结构翻转的能垒是42 7kJ mol 10 2 kcal mol 2 碗烯IUPAC名Dibenzo ghi mno fluoranthene二苯并 ghi mno 熒蒽别名 心環烯 5 環烯识别CAS号 5821 51 2 PubChem 11831840ChemSpider 10006487SMILES c16ccc2ccc3ccc5c4c c1c2c34 c cc5 cc6InChI 1 C20H10 c1 2 12 5 6 14 9 10 15 8 7 13 4 3 11 1 16 17 12 19 14 20 15 18 13 16 h1 10HInChIKey VXRUJZQPKRBJKH UHFFFAOYAF性质化学式 C20H10摩尔质量 250 29 g mol g mol 若非注明 所有数据均出自标准状态 25 100 kPa 下 目录 1 合成 2 芳香性 3 应用 4 参见 5 参考文献合成 编辑通过快速真空裂解技术得到的碗烯纯度比溶液法低 但同时能得到各种碗烯衍生物 1966年 碗烯首次由多步有机合成并从产物中分离出来 3 4 5 由 荧 蒽 的溴代衍生物在碱催化下通过分子内的亲核取代关环得四溴代的碗烯 再由过量的正丁基锂通过卤素 锂交换除溴 经水解得到碗烯 有合成含不同官能团的碗烯衍生物的研究 例如含乙炔基 2 6 7 醚键 8 硫醚 9 含铂官能团 10 芳基 11 萉 12 和茚的并环 13 14 的碗烯衍生物 芳香性 编辑一种解释碗烯芳香性的模型将碗烯分成中间6电子和外围14电子的两个芳香性的共轭体系 这个模型由1966年首次合成碗烯的巴特和劳顿提出 3 他们还给出了这个化合物的命名建议 corannulene意为核 轮烯 然而 之后理论计算的结果并不支持这种模型 15 16 应用 编辑 球碳捕手 碗烯被用于主客体化学的研究 例如碗烯基团与富勒烯 17 18 和硝基苯之间的p重叠 19 长脂肪烃基侧链取代碗烯存在热致变的六角形柱状液晶的中间相 20 碗烯基团也被用于树形高分子的组装 11 或研究其作为配体的性质 21 22 23 24 25 26 27 乙炔基碗烯衍生物对于制造蓝光发射器有潜在的应用价值 7 参见 编辑蒄 螺烯参考文献 编辑 Scott L T Bronstein H E Preda D V Ansems R B M Bratcher M S Hagen Stefan Geodesic polyarenes with exposed concave surfaces Pure and Applied Chemistry Walter de Gruyter GmbH 1999 01 28 71 2 ISSN 1365 3075 doi 10 1351 pac199971020209 2 0 2 1 Scott Lawrence T Hashemi Mohammed M Bratcher Matthew S Corannulene bowl to bowl inversion is rapid at room temperature Journal of the American Chemical Society American Chemical Society ACS 1992 114 5 1920 1921 ISSN 0002 7863 doi 10 1021 ja00031a079 3 0 3 1 Barth Wayne E Lawton Richard G Dibenzo ghi mno fluoranthene Journal of the American Chemical Society American Chemical Society ACS 1966 88 2 380 381 ISSN 0002 7863 doi 10 1021 ja00954a049 Scott Lawrence T Hashemi Mohammed M Meyer Dayton T Warren Hope B Corannulene A convenient new synthesis Journal of the American Chemical Society American Chemical Society ACS 1991 113 18 7082 7084 ISSN 0002 7863 doi 10 1021 ja00018a082 Sygula Andrzej Rabideau Peter W A Practical Large Scale Synthesis of the Corannulene System Journal of the American Chemical Society American Chemical Society ACS 2000 122 26 6323 6324 ISSN 0002 7863 doi 10 1021 ja0011461 Wu Yao Ting Bandera Davide Maag Roman Linden Anthony Baldridge Kim K Siegel Jay S Multiethynyl Corannulenes Synthesis Structure and Properties Journal of the American Chemical Society American Chemical Society ACS 2008 130 32 10729 10739 ISSN 0002 7863 doi 10 1021 ja802334n 7 0 7 1 Mack James Vogel Philip Jones Derek Kaval Necati Sutton Art The development of corannulene based blue emitters Organic amp Biomolecular Chemistry Royal Society of Chemistry RSC 2007 5 15 2448 ISSN 1477 0520 doi 10 1039 b705621d Gershoni Poranne Renana Pappo Doron Solel Ephrath Keinan Ehud Corannulene Ethers via Ullmann Condensation Organic Letters American Chemical Society ACS 2009 11 19 11 22 5146 5149 ISSN 1523 7060 doi 10 1021 ol902352k Baldridge Kim K Hardcastle Kenneth I Seiders T Jon Siegel Jay S Synthesis structure and properties of decakis phenylthio corannulene Org Biomol Chem Royal Society of Chemistry RSC 2010 8 1 53 55 ISSN 1477 0520 doi 10 1039 b919616a Choi Hyunbong Kim Chulwoo Park Ki Min Kim Jinho Kang Youngjin Ko Jaejung Synthesis and structure of penta platinum s bonded derivatives of corannulene Journal of Organometallic Chemistry Elsevier BV 2009 694 22 3529 3532 ISSN 0022 328X doi 10 1016 j jorganchem 2009 07 015 11 0 11 1 Pappo Doron Mejuch Tom Reany Ofer Solel Ephrath Gurram Mahender Keinan Ehud Diverse Functionalization of Corannulene Easy Access to Pentagonal Superstructure Organic Letters American Chemical Society ACS 2009 03 05 11 5 1063 1066 ISSN 1523 7060 doi 10 1021 ol8028127 Nishida Shinsuke Morita Yasushi Ueda Akira Kobayashi Tadahiro Fukui Kozo Ogasawara Kanako Sato Kazunobu Takui Takeji Nakasuji Kazuhiro Curve Structured Phenalenyl Chemistry Synthesis Electronic Structure and Bowl Inversion Barrier of a Phenalenyl Fused Corannulene Anion Journal of the American Chemical Society American Chemical Society ACS 2008 11 12 130 45 14954 14955 ISSN 0002 7863 doi 10 1021 ja806708j Steinberg Brian D Jackson Edward A Filatov Alexander S Wakamiya Atsushi Petrukhina Marina A Scott Lawrence T Aromatic p Systems More Curved Than C60 The Complete Family of All Indenocorannulenes Synthesized by Iterative Microwave Assisted Intramolecular Arylations Journal of the American Chemical Society American Chemical Society ACS 2009 08 05 131 30 10537 10545 ISSN 0002 7863 doi 10 1021 ja9031852 Corannulenylferrocenes towards a 1D non covalent metal organic nanowire Berit Topolinski Bernd M Schmidt Michael Kathan Sergej I Troyanov and Dieter Lentz Chem Commun 2012 48 6298 6300 doi 10 1039 C2CC32275G Sygula Andrzej Rabideau Peter W Structure and inversion barriers of corannulene its dianion and tetraanion An ab initio study Journal of Molecular Structure THEOCHEM Elsevier BV 1995 333 3 215 226 ISSN 0166 1280 doi 10 1016 0166 1280 94 03961 j Monaco Guglielmo Scott Lawrence T Zanasi Riccardo Magnetic Euripi in Corannulene The Journal of Physical Chemistry A American Chemical Society ACS 2008 09 04 112 35 8136 8147 ISSN 1089 5639 doi 10 1021 jp8038779 Sygula Andrzej Fronczek Frank R Sygula Renata Rabideau Peter W Olmstead Marilyn M A Double Concave Hydrocarbon Buckycatcher Journal of the American Chemical Society American Chemical Society ACS 2007 129 13 3842 3843 ISSN 0002 7863 doi 10 1021 ja070616p Wong Bryan M Noncovalent interactions in supramolecular complexes A study on corannulene and the double concave buckycatcher Journal of Computational Chemistry Wiley Blackwell 2009 01 15 30 1 51 56 ISSN 0192 8651 doi 10 1002 jcc 21022 Kobryn Lesya Henry William P Fronczek Frank R Sygula Renata Sygula Andrzej Molecular clips and tweezers with corannulene pincers Tetrahedron Letters Elsevier BV 2009 50 51 7124 7127 ISSN 0040 4039 doi 10 1016 j tetlet 2009 09 177 Miyajima Daigo Tashiro Kentaro Araoka Fumito Takezoe Hideo Kim Jungeun Kato Kenichi Takata Masaki Aida Takuzo Liquid Crystalline Corannulene Responsive to Electric Field Journal of the American Chemical Society American Chemical Society ACS 2009 01 14 131 1 44 45 ISSN 0002 7863 doi 10 1021 ja808396b Hexahapto Metal Coordination to Curved Polyaromatic Hydrocarbon Surfaces The First Transition Metal Corannulene Complex T Jon Seiders Kim K Baldridge Joseph M O Connor and Jay S Siegel J Am Chem Soc 1997 119 20 pp 4781 4782 doi 10 1021 ja964380t d8 Rhodium and Iridium Complexes of Corannulene Jay S Siegel Kim K Baldridge Anthony Linden and Reto Dorta J Am Chem Soc 2006 128 33 pp 10644 10645 doi 10 1021 ja062110x Petrukhina Marina A Coordination of Buckybowls The First Concave Bound Metal Complex Angewandte Chemie International Edition Wiley Blackwell 2008 02 15 47 9 1550 1552 ISSN 1433 7851 doi 10 1002 anie 200704783 Zhu Bolin Ellern Arkady Sygula Andrzej Sygula Renata Angelici Robert J h6 Coordination of the Curved Carbon Surface of Corannulene C20H10 to h6 arene M2 M Ru Os Organometallics American Chemical Society ACS 2007 26 7 1721 1728 ISSN 0276 7333 doi 10 1021 om0610795 Petrukhina Marina A Sevryugina Yulia Rogachev Andrey Yu Jackson Edward A Scott Lawrence T Corannulene A Preference forexo Metal Binding X ray Structural Characterization of Ru2 O2CCF3 2 CO 4 h2 C20H10 2 Organometallics American Chemical Society ACS 2006 25 22 5492 5495 ISSN 0276 7333 doi 10 1021 om060350f Siegel Jay S Baldridge Kim K Linden Anthony Dorta Reto d8Rhodium and Iridium Complexes of Corannulene Journal of the American Chemical Society American Chemical Society ACS 2006 128 33 10644 10645 ISSN 0002 7863 doi 10 1021 ja062110x Bandera D Baldridge K K Linden A Dorta R and Siegel J S 2011 Stereoselective Coordination of C5 Symmetric Corannulene Derivatives with an Enantiomerically Pure RhI nbd Metal Complex Angewandte Chemie International Edition 50 865 867 doi 10 1002 anie 201006877 取自 https zh wikipedia org w index php title 碗烯 amp oldid 74972854, 维基百科，wiki，书籍，书籍，图书馆，

文章

，阅读，下载，免费，免费下载，mp3，视频，mp4，3gp， jpg，jpeg，gif，png，图片，音乐，歌曲，电影，书籍，游戏，游戏。