|本期目录/Table of Contents|

[1]张雪鹏,姚春瑞,徐云彦,等.AlCl3/ICl催化合成十氯代碗烯(C20Cl10)[J].厦门大学学报(自然科学版),2019,58(01):34-39.[doi:10.6043/j.issn.0438-0479.201804019]
 ZHANG Xuepeng,YAO Chunrui,XU Yunyan,et al.Catalytic synthesis of decachlorocorannulene(C20Cl10)by AlCl3/Icl[J].Journal of Xiamen University(Natural Science),2019,58(01):34-39.[doi:10.6043/j.issn.0438-0479.201804019]
点击复制

AlCl3/ICl催化合成十氯代碗烯(C20Cl10)(PDF/HTML)
分享到:

《厦门大学学报(自然科学版)》[ISSN:0438-0479/CN:35-1070/N]

卷:
58卷
期数:
2019年01期
页码:
34-39
栏目:
研究论文
出版日期:
2019-01-24

文章信息/Info

Title:
Catalytic synthesis of decachlorocorannulene(C20Cl10)by AlCl3/Icl
文章编号:
0438-0479(2019)01-0034-06
作者:
张雪鹏姚春瑞徐云彦张前炎*
厦门大学化学化工学院,福建 厦门 361005
Author(s):
ZHANG XuepengYAO ChunruiXU YunyanZHANG Qianyan*
College of Chemistry and Chemical Engineering,Xiamen University,Xiamen 361005,China
关键词:
十氯代碗烯 十苯硫基碗烯 碗烯衍生物 反应中间体
Keywords:
decachlorocorannulene decakis(phenylthio)corannulene corannulene derivatives reaction intermediate
分类号:
O 613.71; O 622.1; O 622.2
DOI:
10.6043/j.issn.0438-0479.201804019
文献标志码:
A
摘要:
卤代碗烯因其碳卤键具有较高的化学反应活性,被认为是碗烯化学研究中一类非常重要的反应中间体.将三氯化铝和一氯化碘进行组合,提出了一种合成十氯代碗烯的新方法.与已报道的十氯代碗烯合成方法相比,该方法不需要在无水无氧的苛刻反应条件下进行,操作简单,而且将产率由文献报道的60%提高到96%.制备得到的十氯代碗烯可以成功转化为十苯硫基碗烯,证实了十氯代碗烯的确可以由新的氯化方法成功合成.该新型氯化方法为合成一些重要的碗烯衍生物提供了便利.
Abstract:
Among the derivatives of corannulene,corannulene polyhalides(such as pentachloro- and decachloro-corannulene)are considered as a very important reaction intermediate in the chemical study of corannulene due to the high chemical reaction activity of carbon halide bonds.In this paper,we report a new method for the synthesis of decachlorocorannulene.With introducing the combination of aluminum trichloride and iodide chloride,the yield of decachlorocorannulene was improved from 60% to 96%.Furthermore, the new method does not require anhydrous and anaerobic harsh conditions and is easy to operate.The prepared decachlorocorannulene can be successfully converted to decakis(phenylthio)corannulene,which confirmed that the decachlorocorannulene can be successfully synthesized by the new chlorination method.The new chlorination method provides convenience for the synthesis of some important corannulene derivatives.

参考文献/References:

[1] BARTH W E,LAWTON R G.Dibenzo[ghi,mno]fluoranthene[J].J Am Chem Soc,1966,88(2):380-381.
[2] KROTO H W,HEATH J R,O’BRIEN S C,et al.C60:buckminsterfullerene[J].Nature,1985,318(6042):162-163.
[3] AJAYAN P M,LIJIMA S.Smallest carbon nanotube[J].Nature,1992,358(6381):23.
[4] SCOTT L T,JACKSON E A,ZHANG Q Y,et al.A short,rigid,structurally pure carbon nanotube by stepwise chemical synthesis[J].J Am Chem Soc,2012,134(1):107-110.
[5] LAWTON R G,BARTH W E.Synthesis of corannulene[J].J Am Chem Soc,1971,93(7):1730-1745.
[6] MIZYED S,GEORGHIOU P E,BANCU M,et al.Embracing C60 with multiarmed geodesic partners[J].J Am Chem Soc,2001,123(51):12770-12774.
[7] DAWE L N,ALHUJRAN T A,TRAN H A,et al.Corannulene and its penta-tert-butyl derivative co-crystallize 1:1 with pristine C60-fullerene[J].Chemical Communications,2012,48(45):5563-5565.
[8] SYGULA A,RABIDEAU P W.Structure and inversion barriers of corannulene,its dianion and tetraanion:an ab initio study[J].Journal of Molecular Structure: THEOCHEM,1995,333(3):215-226.
[9] RAJESHKUMAR V,YUAN T L,STUPARU M C.Corannulenecarbaldehyde:high-yielding synthesis by Rieche formylation and facile access to a variety of corannulene derivatives[J].European Journal of Organic Chemistry,2016,2016(1):36-40.
[10] SYGULA A,SYGULA R,FRONCZEK F R,et al.Addition of organolithium reagents to corannulene and conformational preferences in 1-alkyl-1,2-dihydrocorannulenes[J].Journal of Organic Chemistry,2002,67(18):6487-6492.
[11] ZHANG Q,KAWASUMI K,SEGAWA Y,et al.Palladium-catalyzed C-H activation taken to the limit.Flattening an aromatic bowl by total arylation[J].J Am Chem Soc,2012,134(38):15664-15667.
[12] KAWASUMI K,ZHANG Q,SEGAWA Y,et al.A grossly warped nanographene and the consequences of multiple odd-membered-ring defects[J].Nature Chemistry,2013,5(9):739-744.
[13] SEIDERS T J,BALDRIDGE K K,ELLIOTT E L,et al.Synthesis and quantum mechanical structure of sym-pentamethylcorannulene and decamethylcorannulene[J].J Am Chem Soc,1999,121(32):7439-7440.
[14] SCHMIDT B M,TOPOLINSKI B,YAMADA M,et al.Fluorinated and trifluoromethylated corannulenes[J].Chemistry,2013,19(41):13872-13880.
[15] MACK J,VOGEL P,JONES D,et al.The development of corannulene-based blue emitters[J].Organic & Biomolecular Chemistry,2007,5(15):2448-2452.
[16] SCOTT L T.Fragments of fullerenes:novel syntheses,structures and reactions[J].Pure and Applied Chemistry,1996,68(2):291-300.
[17] BALDRIDGE K K,HARDCASTLE K I,SEIDERS T J,et al.Synthesis,structure and properties of decakis(phenylthio)corannulene[J].Organic & Biomolecular Chemistry,2010,8(1):53-55.
[18] STEINBERG B D,JACKSON E A,FILATOV A S,et al.Aromatic π-systems more curved than C60:the complete family of all indenocorannulenes synthesized by iterative microwave-assisted intramolecular arylations[J].J Am Chem Soc,2009,131(30):10537-10545.
[19] WU D,SHAO T,MEN J,et al.Superaromatic terpyridines based on corannulene responsive to metal ions[J].Dalton Transactions,2014,43(4):1753-1761.
[20] MISHRA A,ULAGANATHAN M,EDISON E,et al.Polymeric nanomaterials based on the buckybowl motif:synthesis through ring-opening metathesis polymerization and energy storage applications[J].ACS Macro Letters,2017,6:1212-1216.
[21] PAPPO D,MEJUCH T,REANY O,et al.Diverse functionalization of corannulene:easy access to pentagonal superstructure[J].Organic Letters,2009,11(5):1063-1066.
[22] JACKSON E A,STEINBERG B D,BANCU M,et al.Pentaindenocorannulene and tetraindenocorannulene:new aromatic hydrocarbon π systems with curvatures surpassing that of C60[J].J Am Chem Soc,2007,129(3):484-485.
[23] GRUBE G H,ELLIOTT E L,STEFFENS R J,et al.Synthesis and properties of sym-pentasubstituted derivatives of corannulene[J].Organic Letters,2003,5(5):713-716.
[24] MATTARELLA M,HABERL J M,RUOKOLAINEN J,et al.Five-fold symmetric penta-substituted corannulene with gelation properties and a liquid-crystalline phase[J].Chemical Communications,2013,49(65):7204-7206.
[25] POGORELTSEV A,SOLEL E,PAPPO D,et al.Deca-heterosubstituted corannulenes[J].Chemical Communi-cations,2012,48(44):5425-5427.
[26] DENIS P A.Theoretical investigation of the stacking interactions between curved conjugated systems and their interaction with fullerenes[J].Chemical Physics Letters,2011,516(1):82-87.
[27] 徐云彦.十吡咯基碗烯的合成及其超分子自组装[D].厦门:厦门大学,2017:43-48.
[28] TAN Y Z,YANG B,PARVEZ K,et al.Atomically precise edge chlorination of nanographenes and its application in graphene nanoribbons[J].Nature Communications,2013,4:2646.
[29] DENG Y,XU B,CASTRO E,et al.Decakis(arylthio)corannulenes:transferable photochemical and redox parameters and photovoltaic device performance[J].European Journal of Organic Chemistry,2017,2017(29):4338-4342.
[30] IWASHITA A,MATSUO Y,NAKAMURA E.AlCl3-mediated mono-,di-,and trihydroarylation of[60]fullerene[J].Angew Chem Int Ed,2007,46(19):3513-3516.[1] BARTH W E,LAWTON R G.Dibenzo[ghi,mno]fluoranthene[J].J Am Chem Soc,1966,88(2):380-381.
[2] KROTO H W,HEATH J R,O’BRIEN S C,et al.C60:buckminsterfullerene[J].Nature,1985,318(6042):162-163.
[3] AJAYAN P M,LIJIMA S.Smallest carbon nanotube[J].Nature,1992,358(6381):23.
[4] SCOTT L T,JACKSON E A,ZHANG Q Y,et al.A short,rigid,structurally pure carbon nanotube by stepwise chemical synthesis[J].J Am Chem Soc,2012,134(1):107-110.
[5] LAWTON R G,BARTH W E.Synthesis of corannulene[J].J Am Chem Soc,1971,93(7):1730-1745.
[6] MIZYED S,GEORGHIOU P E,BANCU M,et al.Embracing C60 with multiarmed geodesic partners[J].J Am Chem Soc,2001,123(51):12770-12774.
[7] DAWE L N,ALHUJRAN T A,TRAN H A,et al.Corannulene and its penta-tert-butyl derivative co-crystallize 1:1 with pristine C60-fullerene[J].Chemical Communications,2012,48(45):5563-5565.
[8] SYGULA A,RABIDEAU P W.Structure and inversion barriers of corannulene,its dianion and tetraanion:an ab initio study[J].Journal of Molecular Structure: THEOCHEM,1995,333(3):215-226.
[9] RAJESHKUMAR V,YUAN T L,STUPARU M C.Corannulenecarbaldehyde:high-yielding synthesis by Rieche formylation and facile access to a variety of corannulene derivatives[J].European Journal of Organic Chemistry,2016,2016(1):36-40.
[10] SYGULA A,SYGULA R,FRONCZEK F R,et al.Addition of organolithium reagents to corannulene and conformational preferences in 1-alkyl-1,2-dihydrocorannulenes[J].Journal of Organic Chemistry,2002,67(18):6487-6492.
[11] ZHANG Q,KAWASUMI K,SEGAWA Y,et al.Palladium-catalyzed C-H activation taken to the limit.Flattening an aromatic bowl by total arylation[J].J Am Chem Soc,2012,134(38):15664-15667.
[12] KAWASUMI K,ZHANG Q,SEGAWA Y,et al.A grossly warped nanographene and the consequences of multiple odd-membered-ring defects[J].Nature Chemistry,2013,5(9):739-744.
[13] SEIDERS T J,BALDRIDGE K K,ELLIOTT E L,et al.Synthesis and quantum mechanical structure of sym-pentamethylcorannulene and decamethylcorannulene[J].J Am Chem Soc,1999,121(32):7439-7440.
[14] SCHMIDT B M,TOPOLINSKI B,YAMADA M,et al.Fluorinated and trifluoromethylated corannulenes[J].Chemistry,2013,19(41):13872-13880.
[15] MACK J,VOGEL P,JONES D,et al.The development of corannulene-based blue emitters[J].Organic & Biomolecular Chemistry,2007,5(15):2448-2452.
[16] SCOTT L T.Fragments of fullerenes:novel syntheses,structures and reactions[J].Pure and Applied Chemistry,1996,68(2):291-300.
[17] BALDRIDGE K K,HARDCASTLE K I,SEIDERS T J,et al.Synthesis,structure and properties of decakis(phenylthio)corannulene[J].Organic & Biomolecular Chemistry,2010,8(1):53-55.
[18] STEINBERG B D,JACKSON E A,FILATOV A S,et al.Aromatic π-systems more curved than C60:the complete family of all indenocorannulenes synthesized by iterative microwave-assisted intramolecular arylations[J].J Am Chem Soc,2009,131(30):10537-10545.
[19] WU D,SHAO T,MEN J,et al.Superaromatic terpyridines based on corannulene responsive to metal ions[J].Dalton Transactions,2014,43(4):1753-1761.
[20] MISHRA A,ULAGANATHAN M,EDISON E,et al.Polymeric nanomaterials based on the buckybowl motif:synthesis through ring-opening metathesis polymerization and energy storage applications[J].ACS Macro Letters,2017,6:1212-1216.
[21] PAPPO D,MEJUCH T,REANY O,et al.Diverse functionalization of corannulene:easy access to pentagonal superstructure[J].Organic Letters,2009,11(5):1063-1066.
[22] JACKSON E A,STEINBERG B D,BANCU M,et al.Pentaindenocorannulene and tetraindenocorannulene:new aromatic hydrocarbon π systems with curvatures surpassing that of C60[J].J Am Chem Soc,2007,129(3):484-485.
[23] GRUBE G H,ELLIOTT E L,STEFFENS R J,et al.Synthesis and properties of sym-pentasubstituted derivatives of corannulene[J].Organic Letters,2003,5(5):713-716.
[24] MATTARELLA M,HABERL J M,RUOKOLAINEN J,et al.Five-fold symmetric penta-substituted corannulene with gelation properties and a liquid-crystalline phase[J].Chemical Communications,2013,49(65):7204-7206.
[25] POGORELTSEV A,SOLEL E,PAPPO D,et al.Deca-heterosubstituted corannulenes[J].Chemical Communi-cations,2012,48(44):5425-5427.
[26] DENIS P A.Theoretical investigation of the stacking interactions between curved conjugated systems and their interaction with fullerenes[J].Chemical Physics Letters,2011,516(1):82-87.
[27] 徐云彦.十吡咯基碗烯的合成及其超分子自组装[D].厦门:厦门大学,2017:43-48.
[28] TAN Y Z,YANG B,PARVEZ K,et al.Atomically precise edge chlorination of nanographenes and its application in graphene nanoribbons[J].Nature Communications,2013,4:2646.
[29] DENG Y,XU B,CASTRO E,et al.Decakis(arylthio)corannulenes:transferable photochemical and redox parameters and photovoltaic device performance[J].European Journal of Organic Chemistry,2017,2017(29):4338-4342.
[30] IWASHITA A,MATSUO Y,NAKAMURA E.AlCl3-mediated mono-,di-,and trihydroarylation of[60]fullerene[J].Angew Chem Int Ed,2007,46(19):3513-3516.

备注/Memo

备注/Memo:
收稿日期:2018-04-25 录用日期:2018-05-24
基金项目:国家自然科学基金(21771152); 中央高校基本科研业务费专项(20720170028,20720160084)
*通信作者:xmuzhangqy@xmu.edu.cn
更新日期/Last Update: 1900-01-01