Well-defined oligo(pyrrole-2,5-diyl)s by the Ullmann reaction

L. Groenendaal; H.W.I. Peerlings; J.L.J. Dongen, van; E.E. Havinga; J.A.J.M. Vekemans; E.W. Meijer

doi:10.1021/ma00105a015

Well-defined oligo(pyrrole-2,5-diyl)s by the Ullmann reaction

L. Groenendaal, H.W.I. Peerlings, J.L.J. Dongen, van, E.E. Havinga, J.A.J.M. Vekemans, E.W. Meijer

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Abstract

The Ullmann coupling reaction has been used to polymerize N-t-BOC-2,5-dibromopyrrole into well-defined oligo(pyrrole-2,5-diyl)s. After optimization of the reaction conditions, i.e. using 1 wt equiv of Cu-bronze in DMF at 100 "C for 1 h, oligomers up to 25 repeating pyrrole units are obtained. Starting from 5,5‘- and 5,5"-dibrominated N-t-BOC protected bi- and terpyrrole as monomers, the polymerization is slower and a lower degree of polymerization is observed, yielding oligomers with an even lower molecular weight than those resulting from N-t-BOC-2,5-dibromopyrrole. The first 20 oligomers of poly(N-t-BOC-pyrrole)h ave been isolated by preparative HPLC. Characterization of the individual oligomers shows that they all are hydrogen terminated and possess a perfect 2,5-linkage: oligo(pyrro1e-2,5-diyl)s. The isolated oligomers have been used to study the optical and electrical properties of the oligomers as a function of chain length.

Original language	English
Pages (from-to)	116-123
Number of pages	8
Journal	Macromolecules
Volume	28
Issue number	1
DOIs	https://doi.org/10.1021/ma00105a015
Publication status	Published - 1995

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title = "Well-defined oligo(pyrrole-2,5-diyl)s by the Ullmann reaction",

abstract = "The Ullmann coupling reaction has been used to polymerize N-t-BOC-2,5-dibromopyrrole into well-defined oligo(pyrrole-2,5-diyl)s. After optimization of the reaction conditions, i.e. using 1 wt equiv of Cu-bronze in DMF at 100 {"}C for 1 h, oligomers up to 25 repeating pyrrole units are obtained. Starting from 5,5{\textquoteleft}- and 5,5{"}-dibrominated N-t-BOC protected bi- and terpyrrole as monomers, the polymerization is slower and a lower degree of polymerization is observed, yielding oligomers with an even lower molecular weight than those resulting from N-t-BOC-2,5-dibromopyrrole. The first 20 oligomers of poly(N-t-BOC-pyrrole)h ave been isolated by preparative HPLC. Characterization of the individual oligomers shows that they all are hydrogen terminated and possess a perfect 2,5-linkage: oligo(pyrro1e-2,5-diyl)s. The isolated oligomers have been used to study the optical and electrical properties of the oligomers as a function of chain length.",

author = "L. Groenendaal and H.W.I. Peerlings and {Dongen, van}, J.L.J. and E.E. Havinga and J.A.J.M. Vekemans and E.W. Meijer",

year = "1995",

doi = "10.1021/ma00105a015",

language = "English",

volume = "28",

pages = "116--123",

journal = "Macromolecules",

issn = "0024-9297",

publisher = "American Chemical Society",

number = "1",

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T1 - Well-defined oligo(pyrrole-2,5-diyl)s by the Ullmann reaction

AU - Groenendaal, L.

AU - Peerlings, H.W.I.

AU - Dongen, van, J.L.J.

AU - Havinga, E.E.

AU - Vekemans, J.A.J.M.

AU - Meijer, E.W.

PY - 1995

Y1 - 1995

N2 - The Ullmann coupling reaction has been used to polymerize N-t-BOC-2,5-dibromopyrrole into well-defined oligo(pyrrole-2,5-diyl)s. After optimization of the reaction conditions, i.e. using 1 wt equiv of Cu-bronze in DMF at 100 "C for 1 h, oligomers up to 25 repeating pyrrole units are obtained. Starting from 5,5‘- and 5,5"-dibrominated N-t-BOC protected bi- and terpyrrole as monomers, the polymerization is slower and a lower degree of polymerization is observed, yielding oligomers with an even lower molecular weight than those resulting from N-t-BOC-2,5-dibromopyrrole. The first 20 oligomers of poly(N-t-BOC-pyrrole)h ave been isolated by preparative HPLC. Characterization of the individual oligomers shows that they all are hydrogen terminated and possess a perfect 2,5-linkage: oligo(pyrro1e-2,5-diyl)s. The isolated oligomers have been used to study the optical and electrical properties of the oligomers as a function of chain length.

AB - The Ullmann coupling reaction has been used to polymerize N-t-BOC-2,5-dibromopyrrole into well-defined oligo(pyrrole-2,5-diyl)s. After optimization of the reaction conditions, i.e. using 1 wt equiv of Cu-bronze in DMF at 100 "C for 1 h, oligomers up to 25 repeating pyrrole units are obtained. Starting from 5,5‘- and 5,5"-dibrominated N-t-BOC protected bi- and terpyrrole as monomers, the polymerization is slower and a lower degree of polymerization is observed, yielding oligomers with an even lower molecular weight than those resulting from N-t-BOC-2,5-dibromopyrrole. The first 20 oligomers of poly(N-t-BOC-pyrrole)h ave been isolated by preparative HPLC. Characterization of the individual oligomers shows that they all are hydrogen terminated and possess a perfect 2,5-linkage: oligo(pyrro1e-2,5-diyl)s. The isolated oligomers have been used to study the optical and electrical properties of the oligomers as a function of chain length.

U2 - 10.1021/ma00105a015

DO - 10.1021/ma00105a015

M3 - Article

SN - 0024-9297

VL - 28

SP - 116

EP - 123

JO - Macromolecules

JF - Macromolecules

IS - 1

ER -

Well-defined oligo(pyrrole-2,5-diyl)s by the Ullmann reaction

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