Synthesis and characterization of wholly aromatic poly(azomethine)s containing donor–acceptor triphenylamine moieties |
| |
| Authors: | Guey‐Sheng Liou Hung‐Yi Lin Yu‐Lun Hsieh Yi‐Lung Yang |
| |
| Affiliation: | 1. Functional Polymeric Materials Research Laboratory, Department of Applied Chemistry, National Chi Nan University, Puli, Nantou Hsien 54561, Taiwan, People's Republic of ChinaFunctional Polymeric Materials Research Laboratory, Department of Applied Chemistry, National Chi Nan University, Puli, Nantou Hsien 54561, Taiwan, People's Republic of China;2. Functional Polymeric Materials Research Laboratory, Department of Applied Chemistry, National Chi Nan University, Puli, Nantou Hsien 54561, Taiwan, People's Republic of China |
| |
| Abstract: | N‐(4‐nitrophenyl)‐4′,4″‐bisformyl‐diphenylamine was synthesized from N‐(4‐nitrophenyl)‐diphenylamine by the Vilsmeier‐Haack reaction. Soluble aromatic poly(azomethine)s (PAMs) were prepared by the solution polycondensation of N‐(4‐nitrophenyl)‐4′,4″‐bisformyl‐diphenylamine and aromatic diamine in N‐methyl‐2‐pyrrolidone (NMP) at room temperature under reduced pressure. All the PAMs are highly soluble in various organic solvents, such as N,N‐dimethylacetamide (DMAc), chloroform (CHCl3), and tetrahydrofuran (THF). Differential scanning calorimetry (DSC) indicated that these PAMs had glass‐transition temperatures (Tgs) in the range of 170–230 °C, and a 10% weight‐loss temperatures in excess of 490 °C with char yield at 800 °C in nitrogen higher than 60%. These PAMs in NMP solution showed UV‐Vis charge‐transfer (CT) absorption at 405–421 nm and photoluminescence peaks around 462–466 nm with fluorescence quantum efficiency (ΦF) 0.10–0.99%. The highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energy levels of these PAMs can be determined from cyclic voltammograms as 4.86–5.43 and 3.31–3.34 eV, respectively. © 2007 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 45: 4921–4932, 2007 |
| |
| Keywords: | charge transfer electrochemistry functionalization of polymers high performance polymers polycondensation |
|
|
