聚{(3-乙酰基)吡咯-[2,5-二(对硝基苯甲烯)]}的合成与表征

SYNTHESIS AND CHARACTERIZATION OF POLY[(3-ACETYL)PYRROLE-2,5-DIYL(p-NITROBENZYLIDENE)]

通过五步法合成了一种新型窄能隙(Eg在178~194eV之间)、大π共轭高分子———聚{(3乙酰基)吡咯[2,5二(对硝基苯甲烯)]}(PAPNBE).采用氢核磁共振谱、傅利叶红外光谱、紫外可见光谱、分光光度计等分析手段对反应中间产物、聚合物PAPNBE及其前聚物聚{(3乙酰基)吡咯[2,5二(对硝基苯甲烷)]}(PAPNBA)进行了分析.经浓硫酸掺杂后,PAPNBE的电导率(27×10^(-6)S cm)提高了3个数量级进入了半导体的范畴.此外,对PAPNBE在有机溶剂中的溶解度进行了测定。

A novel solubleπ-conjugated polymer,poly[(3-acetyl)pyrrole-2,5-diyl(p-nitrobenzylidene)](PAPNBE)is synthesized by condensation of 3-acetylpyrrole with p-nitrobenzaldehyde.The chemical structure and properties of the intermediates,the precursor,poly[(3-acetyl)pyrrole-2,5-diyl(p-nitrobenzylidane)](PAPNBA),and PAPNBE are characterized by 1H-NMR,FT-IR and UV-Vis spectroscopy.The results show that the pyrrole rings in PAPNBA and PAPNBE mainly exist in the aromatic state and the quinonoid state,respectively.The solubility of PAPNBE in dimethyl sulphoxide(DMSO),dimethyl fomamide(DMF)and N-methyl pyrrolidone(NMP)is 0.13~0.15 g/mL,0.34~0.37 g/mL and 0.41~0.45 g/mL,respectively.The result shows that PAPNBE can be easily solved in polar solvents.The conductivity of PAPNBE doped with concentrated sulfuric acid is 2.7×10^(-6)S/cm.The energy bandgap of PAPNBE is about 1.78~1.94 eV.