A Solution‐processible, n‐dopable polypyrrole derivative

Abstract

In this study, soluble, n-dopable, florescent, electrochromic polypyrrole derivative was synthesized through both chemical and electrochemical polymerization of 2-[6-(1H-pyrrol-1-yl)hexyl]-1H-benzo[de]isoquinoline-1,3(2H)-dione (PyNI). The polymer synthesized through chemical polymerization had PL emission maxima at 471 and 543 nm and exhibited two redox couples at E 1/2,p ¼ À1.48 V and E 1/2,p ¼ 1.12 V due to n-type and p-type doping, respectively. Electrochromic properties of electrochemically synthesized poly(PyNI) (PPyNI) were investigated via spectroelectrochemistry, kinetic studies, coloration efficiency, and colorimetry measurements. The optical band gap of PPyNI was calculated as 2.99 and 2.37 eV. Spectroelec-trochemistry analysis of PPyNI reflected electronic transitions at 330-418 nm and 704 nm due to p-p* transition and charge carrier band formation, respectively. The polymer exhibited a switching time of 1.63 s and an optical contrast of 33.37%. Furthermore, dual-type, complementary-colored polymer electrochromic device in ITO/PPyNI/PEDOT/ITO configuration was assembled and characterized. V C 2012 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 50: [4847][4848][4849][4850][4851][4852][4853] 2012

A magenta polypyrrole derivatised with Methyl Red azo dye: synthesis and spectroelectrochemical characterisation

“…The absorption spectrum of the PMRPy film in the dedoped state (after immersion in NaOH solution and washing with H 2 O and CH 3 CN) exhibited a band with maximum (l max ) at 412 nm corresponding to p-p* transition, whilst the absorption spectra of the PPy/MR and PPy films presented bands with l max at 410 nm and 370 nm, respectively. According to the literature, the absorption spectrum of the PPy in the dedoped state is dominated by a broad, single absorption band at around 370-400 nm [45,46], corroborating with our results. The bathochromic shift in the absorption spectra of PPy/MR when compared to the pristine PPy may be associated to the narrowing in the band gap energy (E g ) of PPy/MR due to the increase of the planarity of the polymer.…”

“…S6). [45], in this work, the inclusion of MR unit in the Py ring is shown to have a significant impact on PPy properties and its spectroelectrochemical behaviour in function of the solvent and/or pH variation. In LiClO 4 /CH 3 CN the polymer film previously treated with NaOH (yellow) becomes magenta when oxidised (doped with ClO 4 À ).…”

Mild and selective hydrogenation of aromatic and aliphatic (di)nitriles with a well-defined iron pincer complex

“…1, the bulk polymer Nylon-6,6 and a small selection of pharmaceuticals are shown. Thus, the synthesis of primary amines and particularly primary diamines are of significant interest as intermediates in academic and industrial research 15,[42][43][44][45] . These products can easily be modified by follow-up reactions to obtain secondary amines, for example, via reductive amination or N-methylation, representing useful active drugs.…”

Ferrocene clicked polypyrrole derivatives: effect of spacer group on electrochemical properties and post-polymerization functionalization

“…Following the first scan, Py3Fc revealed ill-defined redox behavior presumably due to interaction of ferrocenium ion (Fc + ) with radical cation of pyrrole, whereby inhibiting the oxidative coupling of radical cations ( Figure S17). [16,34] Figure 3(a) represents the cyclic voltammogram of Py6Fc in TBAPF 6 /DCM. As we could see Py6Fc revealed two well-defined reversible redox process with peak potentials of E ox,1 : 0.21 V and E ox,2 : 0.35 V. Following several potentiodynamic switches between −0.5 and 1.0 V, an electroactive, well-adhered polymer film [35] readily deposited on ITo electrode, which showed linear increase in current densities with increase in scan rate (Figure 3(b), Figure S21).…”