Poly-p-phenyleneamineimine: synthesis and comparison to polyaniline

Wudl, Fred; Angus, R.O; Lu, Fangfang; Allemand, P. M.; Vachon, David J.; Nowak, Michael J.; Liu, Z. X.; Schäffer, H.; Heeger, A.J.

doi:10.1021/ja00246a026

Cited by 332 publications

(137 citation statements)

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“…In particular, a system of absorption bands at 1625 cm À1 (1632 cm À1 in our sample), 1445 and 1414 cm À1 (here probably fused in the one large band peaking at 1405 cm À1 ), at 857 cm À1 (853 cm À1 in our sample) and are at 695 cm À1 are attributed to phenazines formed through inter/intra-molecular cyclization of either quinoid or benzenoid units upon oxidative degradation [42,44]. Furthermore, these structures may also be formed in the initiation stage of polymerization as a consequence of ortho-coupling of aniline molecules as suggested by an early work of Wudl et al [45], further supported by the work of Stejskal and co-authors [36]. The ortho-coupled units can be further converted by oxidative intramolecular cyclization to N-phenylphenazine and others phenazines, as reported in Scheme 3.…”

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confidence: 58%

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A new route for the preparation of flexible skin–core poly(ethylene-co-acrylic acid)/polyaniline functional hybrids

Scaffaro

Dispenza

et al. 2011

Reactive and Functional Polymers

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a b s t r a c tSurface modification of polymeric films is a way to obtain final products with high performance for many specific and ad hoc tailored applications, e.g. in functional packaging, tissue engineering or (bio)sensing. The present work reports, for the first time, on the design and development of surface modified ethyleneacrylic acid copolymer (EAA) films with polyaniline (PANI), with the aim of inducing electrical conductivity and potentially enable the electronic control of a range of physical and chemical properties of the film surface, via a new ''grafting from'' approach. In particular, we demonstrate that PANI was successfully polymerized and covalently grafted onto flexible EAA substrates, previously activated. The final hybrid materials and the corresponding intermediates were fully characterized via FTIR, XPS, SEM-EDAX, mechanical and electrical tests. The mechanical properties of the films are not detrimentally affected by each treatment step, while a significant increase in electrical conductivity was achieved for the new hybrid materials.

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confidence: 58%

“…This result would suggest that the initiation step of the polymerization occurring in the bulk of the aqueous solution likely involves ortho-coupling of neutral aniline monomers [36,45]. These elements are subsequently transformed into phenazine-rich chains that precipitate from water at the increase of molecular weight.…”

mentioning

confidence: 99%

A new route for the preparation of flexible skin–core poly(ethylene-co-acrylic acid)/polyaniline functional hybrids

Scaffaro

Dispenza

et al. 2011

Reactive and Functional Polymers

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“…The reflectance FTIR spectrum of N-PAPANI, Figure 1, showed that the ratio of absorption intensity at 1594 cm -1 due to the quinoid ring to that at 1506 cm -1 due to the benzenoid ring is 1:3 [22,23]. The presence of weak to medium, C-N aliphatic absorptions at 1020 cm -1 and 1249 cm -1 due to primary aliphatic amine [24] and also the presence of an another absorption peak at 1265 cm -1 characteristic of aliphatic C-N which is attached to the polymer [25], all together confirm the N-substitution of propylamine on the PANI.…”

Section: Resuslts and Discussionmentioning

confidence: 99%

Synthesis of Functionalized Propylaminepolyanilines and Investigation of Their Properties

Tarassi

Zadehnazari

2016

J. Chil. Chem. Soc.

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In present investigation, N-substituted propylaminepolyaniline (N-PAPANI) was prepared by reaction of dimethylsulfoxide solution of polyaniline (emeraldine) base with sodium hydride, then reacted with 3-chloropropylaminehydrochloride. The N-PAPANI was characterized using reflectance Fourier transformation infrared (FTIR), cyclic voltammetry, UV-vis spectroscopy and chemical analysis. Polyaniline (PANI) was also subjected to a reaction with 3-chloropropylaminehydrochloride and ferric chloride in acetonitrile as solvent under refluxing temperature (85-90 ºC) (Friedel-Craft synthetic method) to produce ring substituted functionalized PAPANI. Characterization of PAPANI was carried out using various aforementioned techniques. PANI and N-PAPANI polymers exhibited strong UV-vis absorption maxima at 273-294 nm in solution. Cyclic voltammograms of the polymers on an indium-tin oxide (ITO)-coated glass substrate exhibited one pair of reversible redox couples at half-wave oxidation potentials (E 1/2 ) around 0.84-0.86 V and 0.88 V, respectively, versus Ag/AgCl in an acetonitrile solution. The obtained polymers showed good solubility in common organic solvents such as tetrahydrofuran and chloroform compared with emeraldine which is difficult to process due to lack of solubility. Furthermore, these polymers are air stable.

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“…Wudl et al [53] disagree with the proposed metallic nature for the conductive state in polyaniline. They argue that the relatively low conductivity and high concentration of Curie spins is inconsistent with a true metallic state.…”

Section: Charge Carrier Transportmentioning

confidence: 91%