Polynaphthylenes, 1. Synthesis of soluble poly(3,7‐di‐<i>tert</i>‐butyl‐1,5‐naphthylene) via palladium‐catalyzed coupling

Fahnenstich, Ute; Koch, Karl‐Heinz; Müllen, Kläus

doi:10.1002/marc.1989.030101101

Cited by 44 publications

(20 citation statements)

References 14 publications

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“…In the former case, bromosubstituted arylboronic acids are coupled 15) , while in the latter case dibromosubstituted arylenes are reacted with arylenediboronic acids [16][17][18] . As a suitable method to prepare DPP-containing conjugated polymers we have chosen the AA-BB-type reaction.…”

Section: Synthesis and Properties Of Dpp-monomermentioning

confidence: 99%

“…We now report on novel DPP-containing p-conjugated polymers prepared by the palladium-catalyzed aryl-aryl coupling reaction first reported by Suzuki et al 13,14) This reaction has recently been proven to be the prevalent method for preparation of soluble derivatives of poly(1,4-phenylene) (PPP) 15,16) and other conjugated polymers [17][18][19][20][21] . The DPP-containing monomer used for the coupling reaction was 1,4-dioxo-2,5-dihexyl-3,6-bis(4-bromo-phenyl)pyrrolo [3,4-c]pyrrole (2) obtained from 1,4-dioxo-3,6-bis(4-bromophenyl)pyrrolo[3,4-c]-pyrrole (1) by N-alkylation with 6-bromohexane (Scheme 1).…”

Section: Introductionmentioning

confidence: 94%

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New photoluminescent conjugated polymers with 1,4-dioxo-3,6-diphenylpyrrolo[3,4-c]pyrrole (DPP) and 1,4-phenylene units in the main chain

Beyerlein

Tieke

2000

Macromol. Rapid Commun.

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Section: Synthesis and Properties Of Dpp-monomermentioning

confidence: 99%

Section: Introductionmentioning

confidence: 94%

New photoluminescent conjugated polymers with 1,4-dioxo-3,6-diphenylpyrrolo[3,4-c]pyrrole (DPP) and 1,4-phenylene units in the main chain

Beyerlein

Tieke

2000

Macromol. Rapid Commun.

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“…The title compounds were synthesized as described elsewhere: 1-7 [7] and 8-11 [XI. The cyclic voltammograms in solution were carried out under very dry conditions and are described elsewhere [5,61.…”

Section: Methodsmentioning

confidence: 99%

On the relation between charge‐storage capacity and π‐topology of different oligonaphthylenes

et al. 1992

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Conjugated polymers such as polyacetylene," poly-(p-phenylene)[21 or p~l y p y r r o l e [~~ which can be made conductive by p-or n-doping have been extensively investigated. One of the applications discussed for such electroactive materials is their use as anodic electrodes in secondary lithium battery elements.f3'The most important criterion in the design of polymer electrodes is their charge-storage capacity, which is primarily influenced by i) the number of charges transferred per molecule, ii) the reversibility of the charging and discharging steps, iii) the stability over a number of cycles, and iv) the conductivity of the polymer in the neutral and doped states.In order to optimize conjugated polymers for use in battery elements we have studied the relationship between charge-storage capacity and n-topology. The title compounds are linear (A) and two-dimensional (B) oligonaphthylenes ; their redox behavior has been studied by means of cyclic voltammetry (see scheme 1).Previous cyclovoltammetric experiments on homologous series e.g. of oligo(p-phenylene~inylene)s[~] or oligobphenylene)srsl in solution have suggested that monodisperse oligomeric systems are extremely useful model compounds for elucidating the charging mechanisms of the corresponding polymers.[61 Therefore, we now present a comparative cyclovoltammetric study of the following structurally defined, soluble compounds: i) linear oligo(l,4-naphthylene)s (1-5) and oligo-and poly(l,5-naphthylene)s (6, 7)[71 (Type A); ii) ribbon-type oligo(peri-naphthy1ene)s ("oligorylenes") (8-10) (Type B); and iii) the dimeric biperylenyl ll[*] (see scheme 1).In the cyclic voltammograms of the linear oIigo(l,6naph-thylene)s 1-5I7] the first oxidation potentials appear at an almost identical potential of about 1.3 V. The potentials of higher oxidation states are shifted to less positive values with increasing chain length; from the pentamer 4 onwards, a resolution between the first and second oxidation steps is no

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“…Although t-butylation of naphthalene gave a mixture of the 2,6-and 2,7-di-t-butyl isomers [14] the former could be isolated by repeated co-crystallization with thiourea. Subsequent selective bromination governed by steric demand led to the formation of 1,5-dibromo-3,7-di-tbutylnaphthalene 12 [15]. The series of 2-tri-n-butylstannyl-3-alkylthiophenes [16] 13a, 13c and 13e and that of 1,4-dialkoxy-2,5-divinylbenzenes [17] 14b, 14d and 14f were prepared according to procedures reported in the literature.…”

Section: Synthesis and Characterizationmentioning

confidence: 99%

Poly(naphthylenethiophene)s and poly(naphthylenevinylenephenylenevinylene)s: effect of naphthalene positional isomers on the light emitting properties of their polymers

Zhou

Wang

Lin

et al. 2004

Polymer

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Polynaphthylenes, 1. Synthesis of soluble poly(3,7‐di‐tert‐butyl‐1,5‐naphthylene) via palladium‐catalyzed coupling

Cited by 44 publications

References 14 publications

New photoluminescent conjugated polymers with 1,4-dioxo-3,6-diphenylpyrrolo[3,4-c]pyrrole (DPP) and 1,4-phenylene units in the main chain

New photoluminescent conjugated polymers with 1,4-dioxo-3,6-diphenylpyrrolo[3,4-c]pyrrole (DPP) and 1,4-phenylene units in the main chain

On the relation between charge‐storage capacity and π‐topology of different oligonaphthylenes

Poly(naphthylenethiophene)s and poly(naphthylenevinylenephenylenevinylene)s: effect of naphthalene positional isomers on the light emitting properties of their polymers

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