DOI: 10.1002/macp.200500423. Optical, Electrochemical, Magnetic, and Conductive Properties of New Polyindolocarbazoles and Polydiindolocarbazoles

Optical, Electrochemical, Magnetic, and Conductive Properties of New Polyindolocarbazoles and Polydiindolocarbazoles

10.1002/macp.200500423

Crossref journal-article

Wiley

Macromolecular Chemistry and Physics (311)

Abstract

AbstractSummary: New polyindolocarbazoles (PIC) and polydiindolocarbazoles (PDIC) have been synthesized using Yamamoto polymerization reaction. These polymers have been investigated by cyclic voltammetry, UV‐Vis‐NIR spectroelectrochemistry, electrochemical quartz crystal microbalance, in situ electron spin resonance, and in situ conductivity techniques. Two redox oxidation processes, each involving one electron per repeat unit, produce radical cations (free or π‐dimerized) and dications. Each one‐electron redox process is generally split into two due to the stabilization of mixed‐valence states. The oxidative charge is delocalized over the polyconjugated backbone with neutral‐polaron conductivities in the range 0.002–0.04 S · cm−1 and polaron‐bipolaron conductivities in the range 0.04–0.5 S · cm−1. Conductivities are higher when nitrogen atoms are involved in the conjugation pathway.Structure of P3IC, P3DIC, P2IC, and P2DIC.magnified imageStructure of P3IC, P3DIC, P2IC, and P2DIC.

Bibliography

Blouin, N., Michaud, A., Wakim, S., Boudreault, P. T., Leclerc, M., Vercelli, B., Zecchin, S., & Zotti, G. (2006). Optical, Electrochemical, Magnetic, and Conductive Properties of New Polyindolocarbazoles and Polydiindolocarbazoles. Macromolecular Chemistry and Physics, 207(2), 166â174. Portico.

Authors 8

Nicolas Blouin (first)
Alexandre Michaud (additional)
Salem Wakim (additional)
Pierre‐Luc T. Boudreault (additional)
Mario Leclerc (additional)
Barbara Vercelli (additional)
Sandro Zecchin (additional)
Gianni Zotti (additional)

References 44 Referenced 65

10.1038/347539a0
10.1021/cm049473l
10.1002/1521-4095(20020116)14:2<99::AID-ADMA99>3.0.CO;2-9
10.1021/cm049781j
10.1021/cm049647z
10.1039/b306630d
10.1021/cm049654n
10.1557/JMR.2004.0251
{'key': 'e_1_2_6_9_2', 'first-page': '199', 'volume': '1', 'author': 'Wang C. S.', 'year': '1993', 'journal-title': 'Trends Polym. Sci.'} / Trends Polym. Sci. by Wang C. S. (1993)
10.1021/ja0371810
10.1021/cr040084k
10.1021/cm049786g
10.1021/jo049419o
10.1021/ol048543r
{'key': 'e_1_2_6_15_2', 'first-page': '1223', 'author': 'Wakim S.', 'year': '2005', 'journal-title': 'Synlett'} / Synlett by Wakim S. (2005)
10.1021/ja0456149
10.1002/marc.1991.030120806
10.1039/a900447e
10.1021/ma034849m
10.1021/ma034929q
10.1002/adfm.200304344
10.1002/macp.200300219
10.1055/s-2003-37504
{'key': 'e_1_2_6_24_2', 'first-page': '487', 'author': 'Rault‐Berthelot J.', 'year': '1987', 'journal-title': 'New J. Chem.'} / New J. Chem. by Rault‐Berthelot J. (1987)
10.1021/jm00220a017
10.1002/9780470132449.ch23 / Inorg. Synth. by Coulson D. R. (1971)
10.1016/0379-6779(89)90802-3
10.1016/S0065-2725(01)80012-X
10.1016/S0040-4020(03)00029-2
10.1002/ejoc.200400087
{'key': 'e_1_2_6_31_2', 'first-page': '1187', 'author': 'Wahlström N.', 'year': '2004', 'journal-title': 'Synthesis'} / Synthesis by Wahlström N. (2004)
10.1039/jr9650004831
10.1055/s-1969-34189
{'key': 'e_1_2_6_34_2', 'volume-title': 'Organophosphorus Reagents in Organic Synthesis', 'author': 'Cadogan J. I. G.', 'year': '1979'} / Organophosphorus Reagents in Organic Synthesis by Cadogan J. I. G. (1979)
10.1021/ja000759a
{'key': 'e_1_2_6_36_2', 'first-page': '127', 'author': 'Appukkuttan P.', 'year': '2005', 'journal-title': 'Synlett'} / Synlett by Appukkuttan P. (2005)
10.1002/adma.200401290
10.1021/ma00030a003
10.1021/ma9914366
10.1021/ma0355453
10.1063/1.1857477
10.1021/jp982593u
10.1021/j100398a051
10.1002/adma.19930050706

Dates

Type	When
Created	19 years, 7 months ago (Jan. 10, 2006, 6:16 a.m.)
Deposited	1 year, 10 months ago (Oct. 16, 2023, 6:01 a.m.)
Indexed	1 month, 4 weeks ago (July 3, 2025, 12:24 a.m.)
Issued	19 years, 7 months ago (Jan. 10, 2006)
Published	19 years, 7 months ago (Jan. 10, 2006)
Published Online	19 years, 7 months ago (Jan. 10, 2006)
Published Print	19 years, 7 months ago (Jan. 23, 2006)

Funders 0

None

BibTeX

@article{Blouin_2006, title={Optical, Electrochemical, Magnetic, and Conductive Properties of New Polyindolocarbazoles and Polydiindolocarbazoles}, volume={207}, ISSN={1521-3935}, url={http://dx.doi.org/10.1002/macp.200500423}, DOI={10.1002/macp.200500423}, number={2}, journal={Macromolecular Chemistry and Physics}, publisher={Wiley}, author={Blouin, Nicolas and Michaud, Alexandre and Wakim, Salem and Boudreault, Pierre‐Luc T. and Leclerc, Mario and Vercelli, Barbara and Zecchin, Sandro and Zotti, Gianni}, year={2006}, month=jan, pages={166–174} }

JSON

{
  "indexed": {
    "date-parts": [
      [
        2025,
        7,
        3
      ]
    ],
    "date-time": "2025-07-03T04:24:04Z",
    "timestamp": 1751516644347
  },
  "reference-count": 44,
  "publisher": "Wiley",
  "issue": "2",
  "license": [
    {
      "start": {
        "date-parts": [
          [
            2006,
            1,
            10
          ]
        ],
        "date-time": "2006-01-10T00:00:00Z",
        "timestamp": 1136851200000
      },
      "content-version": "vor",
      "delay-in-days": 0,
      "URL": "http://onlinelibrary.wiley.com/termsAndConditions#vor"
    }
  ],
  "content-domain": {
    "domain": [],
    "crossmark-restriction": false
  },
  "published-print": {
    "date-parts": [
      [
        2006,
        1,
        23
      ]
    ]
  },
  "abstract": "<jats:title>Abstract</jats:title><jats:p><jats:bold>Summary:</jats:bold> New polyindolocarbazoles (PIC) and polydiindolocarbazoles (PDIC) have been synthesized using Yamamoto polymerization reaction. These polymers have been investigated by cyclic voltammetry, UV\u2010Vis\u2010NIR spectroelectrochemistry, electrochemical quartz crystal microbalance, in situ electron spin resonance, and in situ conductivity techniques. Two redox oxidation processes, each involving one electron per repeat unit, produce radical cations (free or <jats:italic>\u03c0</jats:italic>\u2010dimerized) and dications. Each one\u2010electron redox process is generally split into two due to the stabilization of mixed\u2010valence states. The oxidative charge is delocalized over the polyconjugated backbone with neutral\u2010polaron conductivities in the range 0.002\u20130.04 S\u2009\u00b7\u2009cm<jats:sup>\u22121</jats:sup> and polaron\u2010bipolaron conductivities in the range 0.04\u20130.5 S\u2009\u00b7\u2009cm<jats:sup>\u22121</jats:sup>. Conductivities are higher when nitrogen atoms are involved in the conjugation pathway.</jats:p><jats:p><jats:boxed-text content-type=\"graphic\" position=\"anchor\"><jats:caption><jats:p>Structure of P3IC, P3DIC, P2IC, and P2DIC.</jats:p></jats:caption><jats:graphic xmlns:xlink=\"http://www.w3.org/1999/xlink\" mimetype=\"image/gif\" position=\"anchor\" specific-use=\"enlarged-web-image\" xlink:href=\"graphic/mgra001.gif\"><jats:alt-text>magnified image</jats:alt-text><jats:caption><jats:p>Structure of P3IC, P3DIC, P2IC, and P2DIC.</jats:p></jats:caption></jats:graphic></jats:boxed-text>\n</jats:p>",
  "DOI": "10.1002/macp.200500423",
  "type": "journal-article",
  "created": {
    "date-parts": [
      [
        2006,
        1,
        10
      ]
    ],
    "date-time": "2006-01-10T11:16:35Z",
    "timestamp": 1136891795000
  },
  "page": "166-174",
  "source": "Crossref",
  "is-referenced-by-count": 65,
  "title": "Optical, Electrochemical, Magnetic, and Conductive Properties of New Polyindolocarbazoles and Polydiindolocarbazoles",
  "prefix": "10.1002",
  "volume": "207",
  "author": [
    {
      "given": "Nicolas",
      "family": "Blouin",
      "sequence": "first",
      "affiliation": []
    },
    {
      "given": "Alexandre",
      "family": "Michaud",
      "sequence": "additional",
      "affiliation": []
    },
    {
      "given": "Salem",
      "family": "Wakim",
      "sequence": "additional",
      "affiliation": []
    },
    {
      "given": "Pierre\u2010Luc T.",
      "family": "Boudreault",
      "sequence": "additional",
      "affiliation": []
    },
    {
      "given": "Mario",
      "family": "Leclerc",
      "sequence": "additional",
      "affiliation": []
    },
    {
      "given": "Barbara",
      "family": "Vercelli",
      "sequence": "additional",
      "affiliation": []
    },
    {
      "given": "Sandro",
      "family": "Zecchin",
      "sequence": "additional",
      "affiliation": []
    },
    {
      "given": "Gianni",
      "family": "Zotti",
      "sequence": "additional",
      "affiliation": []
    }
  ],
  "member": "311",
  "published-online": {
    "date-parts": [
      [
        2006,
        1,
        10
      ]
    ]
  },
  "reference": [
    {
      "key": "e_1_2_6_1_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1038/347539a0"
    },
    {
      "key": "e_1_2_6_2_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/cm049473l"
    },
    {
      "key": "e_1_2_6_3_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/1521-4095(20020116)14:2<99::AID-ADMA99>3.0.CO;2-9"
    },
    {
      "key": "e_1_2_6_4_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/cm049781j"
    },
    {
      "key": "e_1_2_6_5_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/cm049647z"
    },
    {
      "key": "e_1_2_6_6_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1039/b306630d"
    },
    {
      "key": "e_1_2_6_7_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/cm049654n"
    },
    {
      "key": "e_1_2_6_8_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1557/JMR.2004.0251"
    },
    {
      "key": "e_1_2_6_9_2",
      "first-page": "199",
      "volume": "1",
      "author": "Wang C. S.",
      "year": "1993",
      "journal-title": "Trends Polym. Sci."
    },
    {
      "key": "e_1_2_6_10_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja0371810"
    },
    {
      "key": "e_1_2_6_11_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/cr040084k"
    },
    {
      "key": "e_1_2_6_12_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/cm049786g"
    },
    {
      "key": "e_1_2_6_13_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/jo049419o"
    },
    {
      "key": "e_1_2_6_14_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ol048543r"
    },
    {
      "key": "e_1_2_6_15_2",
      "first-page": "1223",
      "author": "Wakim S.",
      "year": "2005",
      "journal-title": "Synlett"
    },
    {
      "key": "e_1_2_6_16_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja0456149"
    },
    {
      "key": "e_1_2_6_17_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/marc.1991.030120806"
    },
    {
      "key": "e_1_2_6_18_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1039/a900447e"
    },
    {
      "key": "e_1_2_6_19_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ma034849m"
    },
    {
      "key": "e_1_2_6_20_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ma034929q"
    },
    {
      "key": "e_1_2_6_21_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/adfm.200304344"
    },
    {
      "key": "e_1_2_6_22_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/macp.200300219"
    },
    {
      "key": "e_1_2_6_23_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1055/s-2003-37504"
    },
    {
      "key": "e_1_2_6_24_2",
      "first-page": "487",
      "author": "Rault\u2010Berthelot J.",
      "year": "1987",
      "journal-title": "New J. Chem."
    },
    {
      "key": "e_1_2_6_25_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/jm00220a017"
    },
    {
      "key": "e_1_2_6_26_2",
      "doi-asserted-by": "crossref",
      "first-page": "121",
      "DOI": "10.1002/9780470132449.ch23",
      "volume": "13",
      "author": "Coulson D. R.",
      "year": "1971",
      "journal-title": "Inorg. Synth."
    },
    {
      "key": "e_1_2_6_27_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/0379-6779(89)90802-3"
    },
    {
      "key": "e_1_2_6_28_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/S0065-2725(01)80012-X"
    },
    {
      "key": "e_1_2_6_29_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/S0040-4020(03)00029-2"
    },
    {
      "key": "e_1_2_6_30_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/ejoc.200400087"
    },
    {
      "key": "e_1_2_6_31_2",
      "first-page": "1187",
      "author": "Wahlstr\u00f6m N.",
      "year": "2004",
      "journal-title": "Synthesis"
    },
    {
      "key": "e_1_2_6_32_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1039/jr9650004831"
    },
    {
      "key": "e_1_2_6_33_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1055/s-1969-34189"
    },
    {
      "key": "e_1_2_6_34_2",
      "volume-title": "Organophosphorus Reagents in Organic Synthesis",
      "author": "Cadogan J. I. G.",
      "year": "1979"
    },
    {
      "key": "e_1_2_6_35_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja000759a"
    },
    {
      "key": "e_1_2_6_36_2",
      "first-page": "127",
      "author": "Appukkuttan P.",
      "year": "2005",
      "journal-title": "Synlett"
    },
    {
      "key": "e_1_2_6_37_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/adma.200401290"
    },
    {
      "key": "e_1_2_6_38_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ma00030a003"
    },
    {
      "key": "e_1_2_6_39_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ma9914366"
    },
    {
      "key": "e_1_2_6_40_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ma0355453"
    },
    {
      "key": "e_1_2_6_41_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1063/1.1857477"
    },
    {
      "key": "e_1_2_6_42_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/jp982593u"
    },
    {
      "key": "e_1_2_6_43_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/j100398a051"
    },
    {
      "key": "e_1_2_6_44_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/adma.19930050706"
    }
  ],
  "container-title": "Macromolecular Chemistry and Physics",
  "original-title": [],
  "language": "en",
  "link": [
    {
      "URL": "https://onlinelibrary.wiley.com/doi/pdf/10.1002/macp.200500423",
      "content-type": "unspecified",
      "content-version": "vor",
      "intended-application": "similarity-checking"
    }
  ],
  "deposited": {
    "date-parts": [
      [
        2023,
        10,
        16
      ]
    ],
    "date-time": "2023-10-16T10:01:43Z",
    "timestamp": 1697450503000
  },
  "score": 1,
  "resource": {
    "primary": {
      "URL": "https://onlinelibrary.wiley.com/doi/10.1002/macp.200500423"
    }
  },
  "subtitle": [],
  "short-title": [],
  "issued": {
    "date-parts": [
      [
        2006,
        1,
        10
      ]
    ]
  },
  "references-count": 44,
  "journal-issue": {
    "issue": "2",
    "published-print": {
      "date-parts": [
        [
          2006,
          1,
          23
        ]
      ]
    }
  },
  "alternative-id": [
    "10.1002/macp.200500423"
  ],
  "URL": "http://dx.doi.org/10.1002/macp.200500423",
  "relation": {},
  "ISSN": [
    "1022-1352",
    "1521-3935"
  ],
  "subject": [],
  "container-title-short": "Macro Chemistry &amp; Physics",
  "published": {
    "date-parts": [
      [
        2006,
        1,
        10
      ]
    ]
  }
}