Synthesis, photochemical, and electrochemical properties of naphthalene-1,4,5,8-tetracarboxylic acid-bis-(N,N'-bis-(2,2,4(2,4,4)-trimethylhexylpolyimide)) and poly(N,N'-bis-(2,2,4(2,4,4)-trimethyl-6-aminohexyl) 3,4,9,10-perylenetetracarboxdiimide)

Abstract

Two new soluble polymers (naphthalene containing: TH-NPI, perylene containing: TH-PPI) have been synthesized via incorporation of branched chain substituent unit into their backbones. Because of existence of branched alkyl spacer, the polymers showed good solubility in common solvents such as chloroform without sacrificing their stability and caused a red shifted excimer-like emission. Their monomers (TH-NDI and TH-PDI) have been synthesized for comparison. The compounds are characterized by UV vis, IR, MS, DSC, TGA, CV, GPC and viscosity measurements. Polymers TH-NPI and TH-PPI with inherent viscosities of 0.50 and 0.30 dL/g were obtained corresponding to their molecular weights 40,000 and 17,000 respectively. Thermogravimetric analysis (TGA) showed that TH-NDI, TH-NPI TH-PD1, and TH-PPI are thermally stable up to 380, 445, 512 and 515 degrees C respectively. The LUMO energy levels of these compounds are calculated as -3.66, -3.71, -3.62 and -3.61 eV respectively. The red-shifted (TH-NPI: 400-650 nm, TH-PPI: 535-800) excimer-like fluorescence in chloroform is attributed to the formation of ground state complexes probably due to intermolecular and intramolecular pi-stackings of the polymers in solution. The fluorescence lifetimes, quantum yields and singlet-state energies are presented. (c) 2007 Elsevier Ltd. All rights reserved.