Synthesis and characterization of novel photoactive polyamide derived from substituted fluorene by copper (I) catalyst



A novel polyamide has been successfully prepared through the reaction of 2,7-dibromo-9,9-dioctylfluorene with 2,5-dipiperazinedione in the presence of CuI, N,N′-dimethylethylene diamine (DMEDA) and K2CO3 as base mixture and as catalyst. The structures of the monomer and the resulting model compound, as well as the structure, solution viscosity, solubility, molecular weights, thermal behavior, thermal stability, and light absorption and emission spectra of the resulting polyamide were characterized by means of FTIR, elemental analysis, 1H-NMR, 13C-NMR, DSC, TGA, GPC and UV–visible absorption, and fluorescence emission spectrophotometers. The polyamide possesses excellent solubility in organic solvents such as tetrahydrofuran (THF), N-methyl-2-pyrrolidone (NMP), N,N-dimethylacetamide (DMAc), N,N-dimethylformamide (DMF), ethylacetate, acetone, ethanol, pyridine, chloroform, and toluene at room temperature. The polyamide had inherent viscosity of 0.65 dL/g, and molecular weights of Mn= 4.25 × 104 and Mw= 5.99 × 104 g/mol. The polyamide had glass transition temperature (Tg) of 138°C, and 10% weight loss at 350°C in nitrogen. The polyamide showed strong UV absorption and blue emission in solution and in solid state. © 2009 Wiley Periodicals, Inc. J Appl Polym Sci, 2009