DOI: 10.1002/macp.1997.021980517. Soluble poly(1,4‐phenylenevinylene)s and poly(1,4‐phenyleneethynylene)s via suzuki coupling

Soluble poly(1,4‐phenylenevinylene)s and poly(1,4‐phenyleneethynylene)s via suzuki coupling

10.1002/macp.1997.021980517

Crossref journal-article

Wiley

Macromolecular Chemistry and Physics (311)

Abstract

AbstractPoly(1,4‐phenylenevinylene) and poly(1,4‐phenyleneethynylene) were prepared fromtrans‐1,2‐dibromoethylene and 1,4‐bis(2‐bromoethynyl)benzene respectively with aryldiboronic acids by a Suzuki cross‐coupling reaction. The polymers were synthesized in a two‐phase system at room temperature using silver oxide and a Pd catalyst. 3% of biaryl formation is observed as a defect structure in the PPV polymers resulting from coupling of arylboronic acid. Soluble polymers were obtained when the aryldiboronic acid is substituted with long‐chain alkoxy groups.

Bibliography

Koch, F., & Heitz, W. (1997). Soluble poly(1,4âphenylenevinylene)s and poly(1,4âphenyleneethynylene)s via suzuki coupling. Macromolecular Chemistry and Physics, 198(5), 1531â1544. Portico.

Authors 2

Friedrich Koch (first)
Walter Heitz (additional)

References 41 Referenced 73

{'key': 'e_1_2_1_1_2', 'volume-title': 'Handbook of Conductive Polymers', 'author': 'Skotheim T. A.', 'year': '1989'} / Handbook of Conductive Polymers by Skotheim T. A. (1989)
{'key': 'e_1_2_1_2_2', 'volume-title': 'Electroresponsive Molecular and Polymeric Systems', 'author': 'Reynolds J. R.', 'year': '1991'} / Electroresponsive Molecular and Polymeric Systems by Reynolds J. R. (1991)
10.1063/1.101393
10.1038/347539a0
{'key': 'e_1_2_1_5_2', 'first-page': '1991', 'volume': '58', 'author': 'Braun D.', 'year': '1982', 'journal-title': 'J. Appl. Phys. Lett.'} / J. Appl. Phys. Lett. by Braun D. (1982)
10.1002/macp.1990.021910902
M.Morini J. LeMoigne Macromolecules27 562 (1994)
10.1021/ma00072a002
10.1021/ja01502a054
10.1002/macp.1970.021310109
10.1002/nadc.19650132202 / Nachr. Chem. Tech. by Drefahl G. (1965)
10.1021/ma00006a029
{'key': 'e_1_2_1_13_2', 'first-page': '354', 'volume': '32', 'author': 'Cataldo F.', 'year': '1991', 'journal-title': 'Polym. Commun.'} / Polym. Commun. by Cataldo F. (1991)
10.1002/pol.1968.150060439
US‐Patent 3.401.152 (1968) invs.:
{'key': 'e_1_2_1_15_3', 'first-page': '87734', 'volume': '69', 'author': 'Wessling R. A.', 'year': '1986', 'journal-title': 'Chem. Abstr.'} / Chem. Abstr. by Wessling R. A. (1986)
10.1002/pol.1986.140241003
10.1002/masy.19870120112
10.1016/0379-6779(93)90577-J
{'issue': '1', 'key': 'e_1_2_1_19_2', 'first-page': '333', 'volume': '32', 'author': 'Greiner A.', 'year': '1991', 'journal-title': 'Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.)'} / Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.) by Greiner A. (1991)
10.1002/macp.1991.021920419
S.Klingelhöfer C.Schellenberg J.Pommerehne H.Bässler A.Greiner W.Heitz Macromol. Chem. Phys. submitted
{'issue': '2', 'key': 'e_1_2_1_22_2', 'first-page': '75', 'volume': '24', 'author': 'Lakshmikantham M. V.', 'year': '1983', 'journal-title': 'Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.)'} / Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.) by Lakshmikantham M. V. (1983)
10.1002/pola.1986.080240924
10.1002/macp.1990.021910413
10.1021/ma00080a034
10.1002/macp.1994.021950128
V.Percec D. H.Hill in:Step Growth Polymers for High‐Performance Materials ACS Symp. Ser. 624 Washington1996
10.1080/00397918108063618
10.3891/acta.chem.scand.47-0221
10.1021/ja00249a069
10.1021/jo00157a037
{'key': 'e_1_2_1_32_2', 'first-page': '1647', 'volume': '19', 'author': 'Boguslavskaya L. S.', 'year': '1983', 'journal-title': 'J. Org. Chem. USSR (Engl. Transl.)'} / J. Org. Chem. USSR (Engl. Transl.) by Boguslavskaya L. S. (1983)
10.1021/jo01291a002
10.1002/macp.1990.021910903
10.1021/ja01353a039
10.1021/ja00090a004
{'key': 'e_1_2_1_37_2', 'first-page': '488', 'author': 'Coutts I. C. C.', 'year': '1970', 'journal-title': 'J. Chem. Soc.'} / J. Chem. Soc. by Coutts I. C. C. (1970)
H. J.Bestmann H.Frey Liebigs Ann. Chem.2061 (1980) (10.1002/jlac.198019801216)
{'key': 'e_1_2_1_39_2', 'first-page': '337', 'volume': '1', 'author': 'Shubina H.', 'year': '1965', 'journal-title': 'J. Org. Chem. USSR (Engl. Transl.)'} / J. Org. Chem. USSR (Engl. Transl.) by Shubina H. (1965)
10.1246/bcsj.39.1547

Dates

Type	When
Created	22 years, 4 months ago (April 17, 2003, 7:04 a.m.)
Deposited	1 year, 7 months ago (Jan. 9, 2024, 1:34 p.m.)
Indexed	1 week, 1 day ago (Aug. 28, 2025, 8:48 a.m.)
Issued	28 years, 4 months ago (May 1, 1997)
Published	28 years, 4 months ago (May 1, 1997)
Published Online	22 years, 5 months ago (March 12, 2003)
Published Print	28 years, 4 months ago (May 1, 1997)

Funders 0

None

BibTeX

@article{Koch_1997, title={Soluble poly(1,4‐phenylenevinylene)s and poly(1,4‐phenyleneethynylene)s via suzuki coupling}, volume={198}, ISSN={1521-3935}, url={http://dx.doi.org/10.1002/macp.1997.021980517}, DOI={10.1002/macp.1997.021980517}, number={5}, journal={Macromolecular Chemistry and Physics}, publisher={Wiley}, author={Koch, Friedrich and Heitz, Walter}, year={1997}, month=may, pages={1531–1544} }

JSON

{
  "indexed": {
    "date-parts": [
      [
        2025,
        8,
        28
      ]
    ],
    "date-time": "2025-08-28T12:48:54Z",
    "timestamp": 1756385334095
  },
  "reference-count": 41,
  "publisher": "Wiley",
  "issue": "5",
  "license": [
    {
      "start": {
        "date-parts": [
          [
            2003,
            3,
            12
          ]
        ],
        "date-time": "2003-03-12T00:00:00Z",
        "timestamp": 1047427200000
      },
      "content-version": "vor",
      "delay-in-days": 2141,
      "URL": "http://onlinelibrary.wiley.com/termsAndConditions#vor"
    }
  ],
  "content-domain": {
    "domain": [],
    "crossmark-restriction": false
  },
  "published-print": {
    "date-parts": [
      [
        1997,
        5
      ]
    ]
  },
  "abstract": "<jats:title>Abstract</jats:title><jats:p>Poly(1,4\u2010phenylenevinylene) and poly(1,4\u2010phenyleneethynylene) were prepared from<jats:italic>trans</jats:italic>\u20101,2\u2010dibromoethylene and 1,4\u2010bis(2\u2010bromoethynyl)benzene respectively with aryldiboronic acids by a Suzuki cross\u2010coupling reaction. The polymers were synthesized in a two\u2010phase system at room temperature using silver oxide and a Pd catalyst. 3% of biaryl formation is observed as a defect structure in the PPV polymers resulting from coupling of arylboronic acid. Soluble polymers were obtained when the aryldiboronic acid is substituted with long\u2010chain alkoxy groups.</jats:p>",
  "DOI": "10.1002/macp.1997.021980517",
  "type": "journal-article",
  "created": {
    "date-parts": [
      [
        2003,
        4,
        17
      ]
    ],
    "date-time": "2003-04-17T11:04:55Z",
    "timestamp": 1050577495000
  },
  "page": "1531-1544",
  "source": "Crossref",
  "is-referenced-by-count": 73,
  "title": "Soluble poly(1,4\u2010phenylenevinylene)s and poly(1,4\u2010phenyleneethynylene)s via suzuki coupling",
  "prefix": "10.1002",
  "volume": "198",
  "author": [
    {
      "given": "Friedrich",
      "family": "Koch",
      "sequence": "first",
      "affiliation": []
    },
    {
      "given": "Walter",
      "family": "Heitz",
      "sequence": "additional",
      "affiliation": []
    }
  ],
  "member": "311",
  "published-online": {
    "date-parts": [
      [
        2003,
        3,
        12
      ]
    ]
  },
  "reference": [
    {
      "key": "e_1_2_1_1_2",
      "volume-title": "Handbook of Conductive Polymers",
      "author": "Skotheim T. A.",
      "year": "1989"
    },
    {
      "key": "e_1_2_1_2_2",
      "volume-title": "Electroresponsive Molecular and Polymeric Systems",
      "author": "Reynolds J. R.",
      "year": "1991"
    },
    {
      "key": "e_1_2_1_3_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1063/1.101393"
    },
    {
      "key": "e_1_2_1_4_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1038/347539a0"
    },
    {
      "key": "e_1_2_1_5_2",
      "first-page": "1991",
      "volume": "58",
      "author": "Braun D.",
      "year": "1982",
      "journal-title": "J. Appl. Phys. Lett."
    },
    {
      "key": "e_1_2_1_6_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/macp.1990.021910902"
    },
    {
      "key": "e_1_2_1_7_2",
      "unstructured": "M.Morini J. LeMoigne Macromolecules27 562 (1994)"
    },
    {
      "key": "e_1_2_1_8_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ma00072a002"
    },
    {
      "key": "e_1_2_1_9_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja01502a054"
    },
    {
      "key": "e_1_2_1_10_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/macp.1970.021310109"
    },
    {
      "key": "e_1_2_1_11_2",
      "doi-asserted-by": "crossref",
      "first-page": "451",
      "DOI": "10.1002/nadc.19650132202",
      "volume": "13",
      "author": "Drefahl G.",
      "year": "1965",
      "journal-title": "Nachr. Chem. Tech."
    },
    {
      "key": "e_1_2_1_12_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ma00006a029"
    },
    {
      "key": "e_1_2_1_13_2",
      "first-page": "354",
      "volume": "32",
      "author": "Cataldo F.",
      "year": "1991",
      "journal-title": "Polym. Commun."
    },
    {
      "key": "e_1_2_1_14_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/pol.1968.150060439"
    },
    {
      "key": "e_1_2_1_15_2",
      "unstructured": "US\u2010Patent 3.401.152 (1968) invs.:"
    },
    {
      "key": "e_1_2_1_15_3",
      "first-page": "87734",
      "volume": "69",
      "author": "Wessling R. A.",
      "year": "1986",
      "journal-title": "Chem. Abstr."
    },
    {
      "key": "e_1_2_1_16_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/pol.1986.140241003"
    },
    {
      "key": "e_1_2_1_17_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/masy.19870120112"
    },
    {
      "key": "e_1_2_1_18_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/0379-6779(93)90577-J"
    },
    {
      "issue": "1",
      "key": "e_1_2_1_19_2",
      "first-page": "333",
      "volume": "32",
      "author": "Greiner A.",
      "year": "1991",
      "journal-title": "Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.)"
    },
    {
      "key": "e_1_2_1_20_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/macp.1991.021920419"
    },
    {
      "key": "e_1_2_1_21_2",
      "unstructured": "S.Klingelh\u00f6fer C.Schellenberg J.Pommerehne H.B\u00e4ssler A.Greiner W.Heitz Macromol. Chem. Phys. submitted"
    },
    {
      "issue": "2",
      "key": "e_1_2_1_22_2",
      "first-page": "75",
      "volume": "24",
      "author": "Lakshmikantham M. V.",
      "year": "1983",
      "journal-title": "Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.)"
    },
    {
      "key": "e_1_2_1_23_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/pola.1986.080240924"
    },
    {
      "key": "e_1_2_1_24_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/macp.1990.021910413"
    },
    {
      "key": "e_1_2_1_25_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ma00080a034"
    },
    {
      "key": "e_1_2_1_26_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/macp.1994.021950128"
    },
    {
      "key": "e_1_2_1_27_2",
      "unstructured": "V.Percec D. H.Hill in:Step Growth Polymers for High\u2010Performance Materials ACS Symp. Ser. 624 Washington1996"
    },
    {
      "key": "e_1_2_1_28_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1080/00397918108063618"
    },
    {
      "key": "e_1_2_1_29_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.3891/acta.chem.scand.47-0221"
    },
    {
      "key": "e_1_2_1_30_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja00249a069"
    },
    {
      "key": "e_1_2_1_31_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/jo00157a037"
    },
    {
      "key": "e_1_2_1_32_2",
      "first-page": "1647",
      "volume": "19",
      "author": "Boguslavskaya L. S.",
      "year": "1983",
      "journal-title": "J. Org. Chem. USSR (Engl. Transl.)"
    },
    {
      "key": "e_1_2_1_33_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/jo01291a002"
    },
    {
      "key": "e_1_2_1_34_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/macp.1990.021910903"
    },
    {
      "key": "e_1_2_1_35_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja01353a039"
    },
    {
      "key": "e_1_2_1_36_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja00090a004"
    },
    {
      "key": "e_1_2_1_37_2",
      "first-page": "488",
      "author": "Coutts I. C. C.",
      "year": "1970",
      "journal-title": "J. Chem. Soc."
    },
    {
      "key": "e_1_2_1_38_2",
      "doi-asserted-by": "crossref",
      "unstructured": "H. J.Bestmann H.Frey Liebigs Ann. Chem.2061 (1980)",
      "DOI": "10.1002/jlac.198019801216"
    },
    {
      "key": "e_1_2_1_39_2",
      "first-page": "337",
      "volume": "1",
      "author": "Shubina H.",
      "year": "1965",
      "journal-title": "J. Org. Chem. USSR (Engl. Transl.)"
    },
    {
      "key": "e_1_2_1_40_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1246/bcsj.39.1547"
    }
  ],
  "container-title": "Macromolecular Chemistry and Physics",
  "original-title": [],
  "language": "en",
  "link": [
    {
      "URL": "https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fmacp.1997.021980517",
      "content-type": "unspecified",
      "content-version": "vor",
      "intended-application": "text-mining"
    },
    {
      "URL": "https://onlinelibrary.wiley.com/doi/pdf/10.1002/macp.1997.021980517",
      "content-type": "unspecified",
      "content-version": "vor",
      "intended-application": "similarity-checking"
    }
  ],
  "deposited": {
    "date-parts": [
      [
        2024,
        1,
        9
      ]
    ],
    "date-time": "2024-01-09T18:34:50Z",
    "timestamp": 1704825290000
  },
  "score": 1,
  "resource": {
    "primary": {
      "URL": "https://onlinelibrary.wiley.com/doi/10.1002/macp.1997.021980517"
    }
  },
  "subtitle": [],
  "short-title": [],
  "issued": {
    "date-parts": [
      [
        1997,
        5
      ]
    ]
  },
  "references-count": 41,
  "journal-issue": {
    "issue": "5",
    "published-print": {
      "date-parts": [
        [
          1997,
          5
        ]
      ]
    }
  },
  "alternative-id": [
    "10.1002/macp.1997.021980517"
  ],
  "URL": "http://dx.doi.org/10.1002/macp.1997.021980517",
  "relation": {},
  "ISSN": [
    "1022-1352",
    "1521-3935"
  ],
  "subject": [],
  "container-title-short": "Macro Chemistry &amp; Physics",
  "published": {
    "date-parts": [
      [
        1997,
        5
      ]
    ]
  }
}