The synthesis of highly active thiophene ring-containing chromophore components for photonic polymers based on a newly designed route

(Note: The full text of this document is currently only available in the PDF Version )

Shen Yuquan, Zhao Yuxia, Li Zao, Wang Jianghong, Qiu Ling, Liu Shixiong, Zhai Jianfeng and Zhou Jiayun


Abstract

2-Aminothiophene derivatives are the key intermediates for the present synthesis. It is known that the synthesis of 2-aminothiophene is troublesome although it is a rather simple heterocycle. In this work, an early report was newly developed as a basis for the efficient synthesis of thiophene-ring-containing chromophore components for photonic polymers. 2-Amino-5-nitrothiophene and 2-amino-3,5-dinitrothiophene were synthesized in excellent yield. After diazotization, the 2-aminothiophene derivatives were directly treated with N-phenyldiethanolamine to afford two-electron push–pull compounds. A similar styryl compound was also prepared. All of these chromophore molecules have further polymerizable hydroxy groups on one end of the molecule. These compounds are currently showing interesting potential in making highly sensitive, nonlinear optical polymeric materials.


References

  1. P. R. Varanasi, A. K.-Y. Jen, J. Chandrasekhar, I. N. N. Namboothiri and A. Rathna, J. Am. Chem. Soc., 1996, 118, 12443 CrossRef .
  2. S. K. Dayal, S. Ehrenson and R. W. Taft, J. Am. Chem. Soc., 1972, 94, 9113 CrossRef CAS .
  3. V. Steinkopf, Justus Liebigs Ann. Chem., 1913, 403, 17 .
  4. A. K.-Y. Jen, D. K. Joel and F. Gerolamo, EP 0 647 874 A1, 1994(Chem. Abstr., 1994, 123, 170670u) Search PubMed .
  5. D. L. Eck and G. W. Stacy, J. Heterocycl. Chem., 1969, 6, 147 CAS .
  6. F. D. King and D. R. M. Walton, J. Chem. Soc., Chem. Commun., 1974, 256 RSC .
  7. D. B. Baird, A. T. Costello, B. R. Fishwick, R. D. Mcclelland and P. Smith, Br. Pat., 1 394 367, 1975(Chem. Abstr., 1975, 83, p116943c) Search PubMed .
Click here to see how this site uses Cookies. View our privacy policy here.