N-Oxides and N-ylides of π-conjugated poly(arylene)s. Preparation and properties of the polymers

✍ Scribed by Takakazu Yamamoto; Bang-Lin Lee; Hideki Hayashi; Nobuo Saito; Tsukasa Maruyama

• Book ID: 104164623
• Publisher: Elsevier Science
• Year: 1997
• Tongue: English
• Weight: 677 KB
• Volume: 38
• Category: Article
• ISSN: 0032-3861
• DOI: 10.1016/s0032-3861(96)00988-3

✦ Synopsis

Treatment of poly(pyridine-2,5-diyl) PPy, poly(quinoline-2,6-diyl) P(2,6-Q), and poly(naphthyridine-2,6diyl) P(2,6-N) with Hz02 in acetic acid gives quantitatively N-oxidized products of the polymers, PPy-ox, P(2,6-Q)-ox, and P(2,6-N)-diox, respectively. A--T* absorption bands of the original polymers show a hypsochromic shift by 35-50 nm by the N-oxidation. Treatment ofPPy and P(2,6-Q) with tetracyanoethylene oxide affords N-ylidated products with a 10-l 5% degree of N-ylidation. The N-oxidized and ylidated polymers undergo electrochemical reduction in a range of about -1.7 to -2.2V vs Ag/Ag+. The electrochemical reduction is accompanied by colour change, and colours of the reduced polymers are considerably different from those of the original polymers (e.g. PPy). The N-oxidized and -ylidated polymers have a dc. electrical conductivity of 2.8 x lo-'-3.4 x 10m6 Scm-'.