Oxidative polymerization of some monomers with pyrrole moieties—an UV–vis absorption spectroscopy study

Simionescu, C. I.; Cianga, I.; Ivanoiu, Maria; Airinei, Anton; Grigoraş, Mircea; Radu, Ionela

doi:10.1016/s0014-3057(98)00272-9

Cited by 17 publications

(11 citation statements)

References 22 publications

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“…where R is an aromatic residue and Ox is an oxidizable group as 2-pyrrolyl, 2-thienyl or 1-naphthyl [36,37]. By chemical or electrochemical polymerization, polymers containing 2,2 0 -bipyrrolediyl or 2,2 0 -thienyldiyl rings or 1,1 0 -binaphthyl in the main chain, spaced by conjugated sequences containing azomethine units, are obtained.…”

Section: Synthesis Of Pyrrole Functional Polymermentioning

confidence: 99%

Synthesis, characterization and electrochromic properties of a conducting copolymer of pyrrole functionalized polystyrene with pyrrole

Tarkuc

Şahi̇n

Toppare

et al. 2006

Polymer

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Section: Synthesis Of Pyrrole Functional Polymermentioning

confidence: 99%

Synthesis, characterization and electrochromic properties of a conducting copolymer of pyrrole functionalized polystyrene with pyrrole

Tarkuc

Şahi̇n

Toppare

et al. 2006

Polymer

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“…General procedure for bis(iminopyrrole) ligand precursors 2 – 6 : The bis(iminopyrrole) ligand precursors 1,2‐(HNC 4 H 3 ‐C(H)N) 2 ‐C 6 H 4 ( 2 ),18a 1,3‐(HNC 4 H 3 ‐C(H)N) 2 ‐C 6 H 4 ( 3 ),18b 1,4‐(HNC 4 H 3 ‐C(H)N) 2 ‐C 6 H 4 ( 4 ),18c 4,4′‐(HNC 4 H 3 ‐C(H)N) 2 ‐C 6 H 4 ‐C 6 H 4 ( 5 ),18c 1,5‐(HNC 4 H 3 ‐C(H)N) 2 ‐C 10 H 6 ( 6 ),18d were synthesized according to literature procedures with a slight modification. In a round‐bottom flask fitted with a condenser and a CaCl 2 guard tube, two equivalents of 2‐formylpyrrole, one equivalent of the corresponding aromatic diamine, and a catalytic amount of p ‐toluenesulfonic acid were suspended in absolute ethanol (20 mL).…”

Section: Methodsmentioning

confidence: 99%

Luminescent Di‐ and Trinuclear Boron Complexes Based on Aromatic Iminopyrrolyl Spacer Ligands: Synthesis, Characterization, and Application in OLEDs

Suresh

Gomes

Lopes

et al. 2015

Chemistry A European J

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New bis- and tris(iminopyrrole)-functionalized linear (1,2-(HNC4 H3 -C(H)N)2 -C6 H4 (2), 1,3-(HNC4 H3 -C(H)N)2 -C6 H4 (3), 1,4-(HNC4 H3 -C(H)N)2 -C6 H4 (4), 4,4'-(HNC4 H3 -C(H)N)2 -(C6 H4 -C6 H4 ) (5), 1,5-(HNC4 H3 C-(H)N)2 -C10 H6 (6), 2,6-(HNC4 H3 C-(H)N)2 -C10 H6 (7), 2,6-(HNC4 H3 C-(H)N)2 -C14 H8 (8)) and star-shaped (1,3,5-(HNC4 H3 -C(H)N-1,4-C6 H4 )3 -C6 H3 (9)) π-conjugated molecules were synthesized by the condensation reactions of 2-formylpyrrole (1) with several aromatic di- and triamines. The corresponding linear diboron chelate complexes (Ph2 B[1,3-bis(iminopyrrolyl)-phenyl]BPh2 (10), Ph2 B[1,4-bis(iminopyrrolyl)-phenyl]BPh2 (11), Ph2 B[4,4'-bis(iminopyrrolyl)-biphenyl]BPh2 (12), Ph2 B[1,5-bis(iminopyrrolyl)-naphthyl]BPh2 (13), Ph2 B[2,6-bis(iminopyrrolyl)-naphthyl]BPh2 (14), Ph2 B[2,6-bis(iminopyrrolyl)-anthracenyl]BPh2 (15)) and the star-shaped triboron complex ([4',4'',4'''-tris(iminopyrrolyl)-1,3,5-triphenylbenzene](BPh2 )3 (16)) were obtained in moderate to good yields, by the treatment of 3-9 with B(C6 H5 )3 . The ligand precursors are non-emissive, whereas most of their boron complexes are highly fluorescent; their emission color depends on the π-conjugation length. The photophysical properties of the luminescent polyboron compounds were measured, showing good solution fluorescence quantum yields ranging from 0.15 to 0.69. DFT and time-dependent DFT calculations confirmed that molecules 10 and 16 are blue emitters, because only one of the iminopyrrolyl groups becomes planar in the singlet excited state, whereas the second (and third) keeps the same geometry. Compound 13, in which planarity is not achieved in any of the groups, is poorly emissive. In the other examples (11, 12, 14, and 15), the LUMO is stabilized, narrowing the gap between the highest occupied molecular orbital and the lowest unoccupied molecular orbital (HOMO-LUMO), and the two iminopyrrolyl groups become planar, extending the size of the π-system, to afford green to yellow emissions. Organic light-emitting diodes (OLEDs) were fabricated by using the new polyboron complexes and their luminance was found to be in the order of 2400 cd m(-2) , for single layer devices, increasing to 4400 cd m(-2) when a hole-transporting layer is used.

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“…Conductive co-polymers have been the subject of many studies in recent years in the fields of design sensors [1][2][3][4], battery materials [2,3] and electronic devices [2,3,5] due to their electrical [6,7], electrochemical and optical properties [6,7]. Polypyrroles (PPy) with high conductivity [4,8] and environmental stability [4,7,8], and poly(para-phenylene)s (PPP) with excellent mechanical [8][9][10][11][12] and thermal stability [9][10][11], are widely studied.…”

Section: Introductionmentioning

confidence: 99%

A QSPR Study on the Physical Properties of Substituted Polypyrroles and Poly(paraphenylenes)

Yıldırım

Aksoy

Tüzün

et al. 2011

Designed Monomers and Polymers

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In this study, a quantitative structure-property relationship (QSPR) study is carried out to estimate the physical properties of substituted polypyrrole (PPy) and polyparaphenylene (PPP). The effects of the substituted side-chains composed of ε-caprolactone, ethylene and styrene oligomers on the glass transition temperature, cohesive energy and dielectric constant of PPy and PPP are studied and the results are analyzed in terms of backbone structure, the type and the length of the side-chains. It is shown that the T g of the polymers can be lowered upon substitution of flexible side-chains. The cohesive energy is higly dependent on the the strength of the non-bonded interactions and it is increased by incorporation of flexible side-chains. The dielectric constant of the polymers is found to be increased depending on the polarizability and the dipole moment density of the side-chains.

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Oxidative polymerization of some monomers with pyrrole moieties—an UV–vis absorption spectroscopy study

Cited by 17 publications

References 22 publications

Synthesis, characterization and electrochromic properties of a conducting copolymer of pyrrole functionalized polystyrene with pyrrole

Synthesis, characterization and electrochromic properties of a conducting copolymer of pyrrole functionalized polystyrene with pyrrole

Luminescent Di‐ and Trinuclear Boron Complexes Based on Aromatic Iminopyrrolyl Spacer Ligands: Synthesis, Characterization, and Application in OLEDs

A QSPR Study on the Physical Properties of Substituted Polypyrroles and Poly(paraphenylenes)

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