Electrochemical synthesis of poly(1,4‐phenylene) films

Fauvarque, Jean‐François; Petit, Michel-Alain; Digua, Abdelouafi; Froyer, G.

doi:10.1002/macp.1987.021880807

Cited by 62 publications

(11 citation statements)

References 21 publications

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“…Peak current electrochemical reduction (or n ‐doping) potentials ( E pc ) of the polymers are observed in the range from −1.99 to −1.72 V versus Ag + /Ag. The E pc values are located as expected between those of PPP ( E pc = −2.6 V versus Ag + /Ag)46, 47 and quantitatively nitrated PPP (NO 2 / p ‐phenylene = about 1) ( E pc = −1.4 V versus Ag + /Ag),7 in view of the number density (1/2–2/3) of the NO 2 group per phenylene group. The CV charts show an n ‐dedoping peak at about −1.7 V versus Ag + /Ag (e.g., −1.67 versus Ag + /Ag for P1 ).…”

Section: Resultssupporting

confidence: 72%

Synthesis and chemical properties of dielectric polyphenylenes with nitro group

Abe

Tokita

Watanabe

et al. 2008

J of Applied Polymer Sci

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Polyphenylenes consisting of nitrophenylene and didodecyloxy-p-phenylene units have been synthesized by Pd-catalyzed organometallic polycondensation. The polymers showed good solubility and had numberaverage molecular weights (M n ) of 13,000-37,000. Their spin-coated films showed fairly high dielectric constants (e) of 3.75-6.36. The polymers were electrochemically active with electrochemical reduction peaks in the range of À1.72 to À1.99 V versus Ag þ /Ag in an acetonitrile solution of [NEt 4 ]BF 4 (0.10M). The polymer composed of 2,3 0 -dinitrobiphenyl and didodecyloxy-p-phenylene units showed thermotropic liquid crystalline phase at about 240 C. Cast films of the polymer had a birefringent phase at room temperature, suggesting self-assembly of the polymer in the solid. XRD studies revealed that the polymers assumed an ordered structure assisted by aggregation of the long alkoxy side chains in the solid. The polymer main chain in the cast film is considered to be aligned parallel with respect to the surface of substrates.

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Section: Resultssupporting

confidence: 72%

Synthesis and chemical properties of dielectric polyphenylenes with nitro group

Abe

Tokita

Watanabe

et al. 2008

J of Applied Polymer Sci

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“…8). We first address the g(C-H) o.-o.-p. vibration peaks 45 of the 6P molecules. The g(C a -H) vibration of the 6P-end-rings at 760 cm À1 exhibits a blue-shift of 3 cm À1 with increasing 6T content.…”

Section: A-sexithiophene/p-sexiphenylmentioning

confidence: 99%

Phase-separation and mixing in thin films of co-deposited rod-like conjugated molecules

et al. 2010

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We report on the formation of organic-organic thin film heterostructures by co-sublimation, which exhibit either mixing of compounds on the molecular scale or pronounced phase separation into ordered domains on the micrometre scale. The mixed structures may be used as active layers in organic field effect transistors, while phase separation is useful in organic bulk hetero-junction solar cells. Pairs of five rod-like conjugated molecules were co-deposited onto silicon oxide substrates in vacuum. With the five materials: pentacene (PEN), alpha-quaterthiophene (4T), alpha-sexithiophene (6T), psexiphenyl (6P), and alkyl chain substituted a,u-dihexylsexithiophene (DH6T), we investigated molecule pairs, which differ in the length of the molecular conjugated core (CC) and the overall molecular length. Material pairs with similarly sized CC, such as 4T/PEN and 6T/6P, showed the formation of ordered layered structures with intimated mixing on a molecular level. On the other hand, pronounced phase separation was observed for material pairs of dissimilar CC lengths, e.g. 4T/6T and PEN/DH6T. We propose that this can be generalized as design rule for the formation of either mixed or phase separated co-deposited molecular films.

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“…Poly( p -phenylene) (PPP)-based polymers are a class of conducting polymers with the repeating units containing the rigid-rod component of p -phenyl; − in recent decades, they have attracted extensive research interests because of extraordinary properties such as excellent thermal and chemical resistances, high mechanical and self-lubricating properties, and unique electrical and photoelectrical characteristics. − However, the unsubstituted PPP is infusible and insoluble in common organic solvents due to high rigidity of its macromolecular backbone, making the synthesis and direct processing intractable; as a result, many potential applications are restricted. , To address this problem, numerous approaches have been studied, for example, preparing PPP thin films by electrochemical polymerization , and surface-assisted syntheses, − synthesizing soluble substituted PPP-based polymers (i.e., PPP derivations) via the approaches including design and synthesis of novel monomers, , copolymerization, , and incorporation of other chemical components (e.g., alkyl/alkoxy, , aryl, carboxyl, and ester groups , ) as side chains in the repeating units. Although various PPP-based polymers have been made through the above approaches and have been demonstrated for many electronic applications such as light-emitting diodes, − solar cells, , and fuel cells, these PPP-based polymers generally have low molecular weights, and they are often produced as powders, dilute solutions, or thin films on substrates (e.g., indium tin oxide (ITO) and metal).…”

Section: Introductionmentioning

confidence: 99%

An Innovative Approach for the Preparation of High-Performance Electrospun Poly(p-phenylene)-Based Polymer Nanofiber Belts

Ding

Yang

et al. 2017

Macromolecules

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The aim of this study is to prepare high-performance poly(p-phenylene) (PPP)-based polymer nanofiber belts. The hypothesis is that these nanofiber belts would possess high mechanical properties, excellent thermal and chemical resistances, and unique electrical and photoelectrical characteristics owing to high rigidity of macromolecular backbones. In general, the unsubstituted PPP polymers are infusible and insoluble in common organic solvents; thus, the synthesis and processing of these polymers are intractable. Although some substituted PPP-based polymers (i.e., PPP derivations) are soluble, their molecular weights are too low to be processed into nanofibers (particularly by the electrospinning technique). To date, there has been no report on the preparation of any kind of PPP-based polymer nanofibers. In this study, four soluble PPP-based oligomers of phthalate-capped poly(2,5-benzophenone) (PBPA) with varied molecular weights were synthesized via Ni(II) complex-catalyzed cross-coupling reaction; subsequently, the blend nanofiber belts of poly(2,5-benzophenone)–pyrrolone (PBPY) and polyimide (PI) were made by the combination of electrospinning and molecular coupling assembly techniques followed by heat treatment, wherein the use of poly(amic acid) (PAA, the precursor of PI) as carrier/glue polymer for assisting electrospinning is crucial for successful preparation of the nanofibers. The PBPY/PI nanofiber belts exhibited high mechanical strength, superior thermal stability, and chemical resistance; hence, they could be used as filtration media under high-temperature and/or corrosive conditions, and they could also be used as separators in batteries and supercapacitors. It is important to note that this is the first reported study on the preparation of PPP-based polymer nanofibers; additionally, this study also provides an innovative approach for making nanofibers from the polymers that cannot be electrospun directly.

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Electrochemical synthesis of poly(1,4‐phenylene) films

Cited by 62 publications

References 21 publications

Synthesis and chemical properties of dielectric polyphenylenes with nitro group

Synthesis and chemical properties of dielectric polyphenylenes with nitro group

Phase-separation and mixing in thin films of co-deposited rod-like conjugated molecules

An Innovative Approach for the Preparation of High-Performance Electrospun Poly(p-phenylene)-Based Polymer Nanofiber Belts

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