Articles

Synthesis of Shape-Persistent Phenyl Ethynylene Macrocycles with Intrannular Flexible Oligooxylethylene Chains

  • LI Quan ,
  • ZHENG Ying ,
  • WANG Li ,
  • YI Shou-Bing ,
  • CHENG Xiao-Hong
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  • School of Chemistry Science and Engineering, Key Laboratory of Medicinal Chemistry for Natural Resourse of Ministry of Education, Yunnan University, Kunming 650091

Received date: 2011-01-10

  Revised date: 2011-09-14

  Online published: 2011-09-27

Supported by

Project supported by the Ph.D. Program Foundation of Ministry of Education of China (No. 20070673002).

Abstract

Shape-persistent phenyl ethynylene macrocycles with intraanular flexible oligooxylethylene chains were synthesized by intramolecular Glaser coupling reaction of half rings. The structures of target phenyl ethynylene macrocycles were identified by 1H NMR, 13C NMR, HRMS, UV and PL (photduminescence), The purity of the target macrocycles was determined by GPC. All the macrocycles are nomesogens as indicated by polarized optical microscopy (POM) and differential scanning calorimetry (DSC), the reason is analyzed as the streric hindrance of the intrannular flexible chains which led to the anordered aggregation of the macrocycles.

Cite this article

LI Quan , ZHENG Ying , WANG Li , YI Shou-Bing , CHENG Xiao-Hong . Synthesis of Shape-Persistent Phenyl Ethynylene Macrocycles with Intrannular Flexible Oligooxylethylene Chains[J]. Chinese Journal of Organic Chemistry, 2012 , 32(01) : 81 -87 . DOI: 10.6023/cjoc1101103

References

[1] Cheng, X. H.;Ju, X. P.; H?ger,S. Chin. J.Org.Chem.2006, 26(5),733 (in Chinese)

(程晓红,鞠秀萍,Hoeger,Sigurd,有机化学,2006,26(5),733)

[2] Rosselli, S.; Ramminger, A. D.; Wagner, T.; Silier, B.; Wiegand, S.; H?u?ler,W; Lieser, G.; Scheumann, V.; H?ger, S. Angew. Chem. 2001, 113,3233.

[3] Rosselli, S.; Ramminger, A. D.; Wagner, T.; Lieser, G.; H?ger, S. Chem. Eur. J. 2003, 9, 3481.

[4] H?ger, S.; Morrison, D. L.; Enkelmann,V. J. Am. Chem. Soc. 2002, 124(23), 6734.

[5] Zhang, J. S.; Moore, J. S. J. Am. Chem. Soc. 1994,116,2655.

[6] Fischer, M.; Lieser,G.; Rapp, A.; Schnell, I.; Mamdouh, W.; Feyter, S. D.; Schryver, F. C. D.; H?ger,S. J. Am. Chem. Soc. 2004, 126, 214.

[7] Kawase ,T.; Seirai, Y.; Darabi, H. R.; Oda, M.; Sarakai,Y.; Tashiro, K. Angew Chem. 2003,115(14), 1662.

[8] Kawase,T.; Nishiyama,Y.; Nakamura,T.; Ebi,T.; Matsumoto,K.; Kurata, H.; Oda. M. Angew Chem. 2007,119(7),1104.

[9] Xie, Z.; Zhang, W.; Huang, P. C. Chin. J.Org.Chem. 2002,22(8),543.

(谢政,张炜,黄鹏程,有机化学,2002,22(8),543.)

[10] Moore, J. S. Acc. Chem. Res. 1997, 30, 402.

[11] H?ger,S. J. Poly. Sci.: Part A: Poly. Chem. 1999,37, 2685.

[12] H?ger,S. Chem. Eur. J. 2004, 10, 1320.

[13] Cheng, X. H.; H?ger,S. Chem. J. Chin. Uni.2007,28(1),65.

(程晓红,Sigurd H?ger,高等学校化学学报,2007,28(1),65.)

[14] Liu, W. J. ; Zhou,Y.; Zhou, Q. F.; Ma,Y. G.; Pei, J. Org. Lett.,2008, 10(11),2123.

[15] Staab, H. A.; Neunhoeffer, K. Synthesis 1974,424.

[16] H?ger, S.; Enkelmann,V.; Bonrad, K.; Tschiers,C. Angew. Chem., Int. Ed,2000, 39, 2267.

[17] H?ger, S.; Cheng, X. H.; Ramminger, A. D.; Enkelmann,V.; Rapp, A.; Mondeshki; M.; Schnell,I. Angew. Chem. Int. Ed. 2005, 44, 2801.

[18] H?ger, S.; Weber, J.; Leppert, A.; Enkelmann,V. Beilstein J. Org. chem., 2008, 4, 1.
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