Yq. Shen et al., The synthesis of highly active thiophene ring-containing chromophore components for photonic polymers based on a newly designed route, J CHEM S P1, (24), 1999, pp. 3691-3695
2-Aminothiophene derivatives are the key intermediates for the present synt
hesis. It is known that the synthesis of 2-aminothiophene is troublesome al
though 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-c
ontaining chromophore components for photonic polymers. 2-Amino-5-nitrothio
phene and 2-amino-3,5-dinitrothiophene were synthesized in excellent yield.
After diazotization, the 2-aminothiophene derivatives were directly treate
d with N-phenyldiethanolamine to afford two-electron push-pull compounds. A
similar styryl compound was also prepared. All of these chromophore molecu
les have further polymerizable hydroxy groups on one end of the molecule. T
hese compounds are currently showing interesting potential in making highly
sensitive, nonlinear optical polymeric materials.