Articles

Synthesis and Liquid Crystal Property of 4,5-Disubstituted Phenanthrene and 9,10-Dihydrophenanthrene Derivatives

  • Cao Jianhua ,
  • Li Min ,
  • Sui Yan ,
  • Hua Ruimao
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  • a Beijing Research Center of Shijiazhuang Chengzhi Yonghua Display Material Co. Ltd., Beijing 100084;
    b Hebei Engineering & Technology Center for Flat Panel Display Material, Shijiazhuang 050091;
    c Department of Chemistry, Tsinghua University, Beijing 100084

Received date: 2013-06-20

  Revised date: 2013-07-15

  Online published: 2013-07-26

Supported by

Project supported by the National Natural Science Foundation of China (No. 21032004), the Specialized Research Fund for the Doctoral Program of Higher Education of China (No. 20110002110051) and the National Electronics and Information Industry Development Fund.

Abstract

Using 2-amino-3-substituted benzoic acid as starting material, 4, 5-disubstituted phenanthrene derivatives were synthesized via sequential reactions of diazotization-coupling reaction, esterification, reduction, oxidation and cyclization, and using reduced biphenyl intermediates as starting materials. 4, 5-Disubstituted 9, 10-dihydrophenanthrene derivatives were syn-thesized via sequential reactions of bromination, grinard reaction, using 4, 5-disubstituted phenanthrene and 4, 5-disubstituted 9, 10-dihydrophenanthrene derivatives as starting materials. Liquid crystal monomer compounds were synthesized via sequential reactions of halogenations and coupling reaction, and the chemical structures of products were identified by 1H NMR, 13C NMR spectra.

Cite this article

Cao Jianhua , Li Min , Sui Yan , Hua Ruimao . Synthesis and Liquid Crystal Property of 4,5-Disubstituted Phenanthrene and 9,10-Dihydrophenanthrene Derivatives[J]. Chinese Journal of Organic Chemistry, 2013 , 33(11) : 2349 -2356 . DOI: 10.6023/cjoc201306029

References

[1] Xu,H.Ph.D.Dissertation,Jilin University,Changchun,2009 (in Chinese).(许海,博士论文,吉林大学,长春,2009.)

[2] Dubois,F.; Gingras,M.Tetrahedron Lett.1998,39,5039.

[3] Kharasch,M.S.; Nudenberg,W.; Fields,E.K.J.Am.Chem.Soc.1944,66,1276.

[4] Campeau,L.C.; Parisien,M.; Jean,A.; Fagnou,K.J.Am.Chem.Soc.2006,128,581.

[5] Brown,C.; Sikkel,B.J.; Carvalho,C.F.; Sargent,M.V.J.Chem.Soc.,Perk.Trans.1 1982,3007.

[6] Shi,M.; Xu,B.J.Org.Chem.2002,67,294.

[7] Kuninobu,Y.; Tatsuzaki,T.; Matsuki,T.; Takai,K.J.Org.Chem.2011,76,7005.

[8] Some,S.; Dutta,B.; Ray,J.K.Tetrahedron Lett.2006,47,1221.

[9] Bacon,L.J.Chem.Soc.1958,1375.

[10] Cosmo,R.; Sternhell,S.Aust.J.Chem.1987,40,35.

[11] Yosuke,N.; Takahiro,F.; Sachiko,S.; Jun,N.Chem.Lett.1999,10,1039.

[12] Tian,H.; Shi,J.; Dong,S.; Yan,D.; Wang,L.-X.; Geng,Y.; Wang,F.S.Chem.Commun.2006,33,3498.

[13] Cosmo,R.; Sternhell,S.Australian J.Chem.1987,40,2137.

[14] Witting,G.; Zimmermann,H.Chem.Ber.1953,86,629.

[15] Newman,M.S.; Lilje,K.C.J.Org.Chem.1979,44,4944.

[16] Ramurthy,S.; Lin,X.; Subramanian,S.; Rico,A.C.; Wang,X.M.; Jain,R.; Murray,J.M.; Bashman,S.E.; Warne,R.L.; Shu,W.; Zhou,Y.; Dove,J.; Aikawa,M.; Amiri,P.; Wang,W.; Jensen,J.M.; Wagman,A.S.; Pfister,K.B.; Ng,S.C.WO 2007117607,2007 [Chem.Abstr.2007,147,469365].

[17] Ligtenbarg,A.G.J.; Beuken,E.K.; Meetsma,A.; Veldman,N.; Smeets,W.J.J.J.Chem.Soc.1998,2,263.

[18] Dameron,A.A.; Ciszek,J.W.; Tour,J.M.; Weisc,P.S.J.Phys.Chem.B 2004,108,16761.

[19] Ciszek,J.W.; Tour,J.M.Tetrahedron Lett.2004,45,2801.

[20] Kawamura,M.; Funahashi,M.US 20070029927,2007 [Chem.Abstr.2007,146,216108].

[21] Helms,A.; Heiler,D.; Mclendon,G.J.Am.Chem.Soc.1992,114,6227.

[22] Vonlanthen,D.; Rotzler,J.; Neuburger,M.; Mayor,M.Eur.J.Org.Chem.2010,75,120.

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