DOI: 10.1002/macp.200700158. Effects of Acceptors on the Electronic and Optoelectronic Properties of Fluorene‐Based Donor–Acceptor

Effects of Acceptors on the Electronic and Optoelectronic Properties of Fluorene‐Based Donor–Acceptor–Donor Copolymers

10.1002/macp.200700158

Crossref journal-article

Wiley

Macromolecular Chemistry and Physics (311)

Abstract

AbstractIn this study, four fluorene‐based conjugated copolymers were synthesized to explore the acceptor effects on the electronic and optoelectronic properties. The studied polymers were poly{[2,7‐(9,9‐dihexylfluorene)]‐alt‐[2,2′:5,2″‐terthiophene]} (PFTT) and its derivatives of poly{[2,7‐(9,9′‐dihexylfluorene)]‐alt‐[2,3‐dimethyl‐5,7‐dithien‐2‐yl‐quinoxaline]} (PFDDTQ), poly{[2,7‐(9,9′‐dihexylfluorene)]‐alt‐[4,7‐dithien‐2‐yl‐2,1,3‐benzothiadiazole]} (PFDTBT), and poly{[2,7‐(9,9′‐dihexylfluorene)]‐alt‐[2,3‐dimethyl‐5,7‐dithien‐2‐yl‐thieno[3,4‐b]pyrazine]} (PFDDTTP) with the acceptors of quinoxaline (Q), 2,1,3‐benzothiadiazole (BT), and thieno[3,4‐b]pyrazine (TP), respectively. The order of the band gap was PFDTTP < PFDTBT < PFDDTQ < PFTT, which was on the reverse trend of emission maximum and field‐effect transistor (FET) mobility. The strong acceptor strength of the TP moiety and coplanar backbone in PFDTTP resulted in the highest intramolecular charge transfer (ICT) among the four polymers. The FET mobility of PFDTTP could be varied by two orders of magnitude through the solvent quality. The present study suggested the importance of the acceptor structure on the electronic and optoelectronic properties of semiconducting polymers.magnified image

Bibliography

Lee, W., Cheng, K., Wang, T., Chueh, C., Chen, W., Tuan, C., & Lin, J. (2007). Effects of Acceptors on the Electronic and Optoelectronic Properties of FluoreneâBased DonorâAcceptorâDonor Copolymers. Macromolecular Chemistry and Physics, 208(17), 1919â1927. Portico.

Authors 7

Wen‐Ya Lee (first)
Kai‐Fang Cheng (additional)
Then‐Fu Wang (additional)
Chu‐Chen Chueh (additional)
Wen‐Chang Chen (additional)
Chih‐Shen Tuan (additional)
Jen‐Lien Lin (additional)

References 43 Referenced 60

10.1039/a902859e
10.1021/cm9801439
10.1021/ma0100448
10.1016/S0927-796X(00)00029-2
10.1021/ma051102i
10.1021/ma061861g
10.1039/b203862e
10.1002/macp.200600128
10.1016/j.polymer.2005.11.058
10.1021/ma049204g
10.1021/ma048118d
10.1002/polb.20997
10.1021/ma020405z
10.1063/1.1406143
10.1063/1.2713139
10.1063/1.2142289
10.1021/cm049825o
10.1021/cm051561y
10.1002/marc.200500616
10.1002/marc.200500276
10.1002/adfm.200305180
10.1002/adma.200390030
10.1021/ma060421m
10.1002/adma.200600124
10.1002/marc.200600237
10.1002/macp.200500517
10.1021/cm050463
10.1007/s00339-003-2498-5
10.1002/adma.200304150
10.1063/1.1825070
10.1002/adfm.200500339
10.1021/cm950467m
10.1055/s-2002-32523
10.1021/ma00106a009
10.1016/j.synthmet.2006.02.013
{'key': 'e_1_2_6_36_2', 'first-page': '47', 'author': 'Wu W. C.', 'year': '2006', 'journal-title': 'J. Polym. Res.'} / J. Polym. Res. by Wu W. C. (2006)
10.1021/ja039772w
10.1021/cm049617w
10.1021/ma047415f
10.1038/nmat1612
10.1021/cm0008563
10.1002/pola.21586
10.1038/nature03376

Dates

Type	When
Created	18 years ago (Aug. 2, 2007, 1:21 p.m.)
Deposited	1 year, 10 months ago (Oct. 14, 2023, 10:46 a.m.)
Indexed	1 day ago (Aug. 29, 2025, 6:17 a.m.)
Issued	18 years ago (Aug. 28, 2007)
Published	18 years ago (Aug. 28, 2007)
Published Online	18 years ago (Aug. 28, 2007)
Published Print	17 years, 11 months ago (Sept. 5, 2007)

Funders 0

None

BibTeX

@article{Lee_2007, title={Effects of Acceptors on the Electronic and Optoelectronic Properties of Fluorene‐Based Donor–Acceptor–Donor Copolymers}, volume={208}, ISSN={1521-3935}, url={http://dx.doi.org/10.1002/macp.200700158}, DOI={10.1002/macp.200700158}, number={17}, journal={Macromolecular Chemistry and Physics}, publisher={Wiley}, author={Lee, Wen‐Ya and Cheng, Kai‐Fang and Wang, Then‐Fu and Chueh, Chu‐Chen and Chen, Wen‐Chang and Tuan, Chih‐Shen and Lin, Jen‐Lien}, year={2007}, month=aug, pages={1919–1927} }

JSON

{
  "indexed": {
    "date-parts": [
      [
        2025,
        8,
        29
      ]
    ],
    "date-time": "2025-08-29T10:17:10Z",
    "timestamp": 1756462630637
  },
  "reference-count": 43,
  "publisher": "Wiley",
  "issue": "17",
  "license": [
    {
      "start": {
        "date-parts": [
          [
            2007,
            8,
            2
          ]
        ],
        "date-time": "2007-08-02T00:00:00Z",
        "timestamp": 1186012800000
      },
      "content-version": "vor",
      "delay-in-days": 0,
      "URL": "http://onlinelibrary.wiley.com/termsAndConditions#vor"
    }
  ],
  "content-domain": {
    "domain": [],
    "crossmark-restriction": false
  },
  "published-print": {
    "date-parts": [
      [
        2007,
        9,
        5
      ]
    ]
  },
  "abstract": "<jats:title>Abstract</jats:title><jats:p>In this study, four fluorene\u2010based conjugated copolymers were synthesized to explore the acceptor effects on the electronic and optoelectronic properties. The studied polymers were poly{[2,7\u2010(9,9\u2010dihexylfluorene)]\u2010<jats:italic>alt</jats:italic>\u2010[2,2\u2032:5,2\u2033\u2010terthiophene]} (<jats:bold>PFTT</jats:bold>) and its derivatives of poly{[2,7\u2010(9,9\u2032\u2010dihexylfluorene)]\u2010<jats:italic>alt</jats:italic>\u2010[2,3\u2010dimethyl\u20105,7\u2010dithien\u20102\u2010yl\u2010quinoxaline]} (<jats:bold>PFDDTQ</jats:bold>), poly{[2,7\u2010(9,9\u2032\u2010dihexylfluorene)]\u2010<jats:italic>alt</jats:italic>\u2010[4,7\u2010dithien\u20102\u2010yl\u20102,1,3\u2010benzothiadiazole]} (<jats:bold>PFDTBT</jats:bold>), and poly{[2,7\u2010(9,9\u2032\u2010dihexylfluorene)]\u2010<jats:italic>alt</jats:italic>\u2010[2,3\u2010dimethyl\u20105,7\u2010dithien\u20102\u2010yl\u2010thieno[3,4\u2010b]pyrazine]} (<jats:bold>PFDDTTP</jats:bold>) with the acceptors of quinoxaline (<jats:bold>Q</jats:bold>), 2,1,3\u2010benzothiadiazole (<jats:bold>BT</jats:bold>), and thieno[3,4\u2010b]pyrazine (<jats:bold>TP</jats:bold>), respectively. The order of the band gap was <jats:bold>PFDTTP</jats:bold>\u2009&lt;\u2009<jats:bold>PFDTBT</jats:bold>\u2009&lt;\u2009<jats:bold>PFDDTQ</jats:bold>\u2009&lt;\u2009<jats:bold>PFTT</jats:bold>, which was on the reverse trend of emission maximum and field\u2010effect transistor (FET) mobility. The strong acceptor strength of the <jats:bold>TP</jats:bold> moiety and coplanar backbone in <jats:bold>PFDTTP</jats:bold> resulted in the highest intramolecular charge transfer (ICT) among the four polymers. The FET mobility of <jats:bold>PFDTTP</jats:bold> could be varied by two orders of magnitude through the solvent quality. The present study suggested the importance of the acceptor structure on the electronic and optoelectronic properties of semiconducting polymers.</jats:p><jats:p><jats:boxed-text content-type=\"graphic\" position=\"anchor\"><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:graphic></jats:boxed-text>\n</jats:p>",
  "DOI": "10.1002/macp.200700158",
  "type": "journal-article",
  "created": {
    "date-parts": [
      [
        2007,
        8,
        2
      ]
    ],
    "date-time": "2007-08-02T17:21:16Z",
    "timestamp": 1186075276000
  },
  "page": "1919-1927",
  "source": "Crossref",
  "is-referenced-by-count": 60,
  "title": "Effects of Acceptors on the Electronic and Optoelectronic Properties of Fluorene\u2010Based Donor\u2013Acceptor\u2013Donor Copolymers",
  "prefix": "10.1002",
  "volume": "208",
  "author": [
    {
      "given": "Wen\u2010Ya",
      "family": "Lee",
      "sequence": "first",
      "affiliation": []
    },
    {
      "given": "Kai\u2010Fang",
      "family": "Cheng",
      "sequence": "additional",
      "affiliation": []
    },
    {
      "given": "Then\u2010Fu",
      "family": "Wang",
      "sequence": "additional",
      "affiliation": []
    },
    {
      "given": "Chu\u2010Chen",
      "family": "Chueh",
      "sequence": "additional",
      "affiliation": []
    },
    {
      "given": "Wen\u2010Chang",
      "family": "Chen",
      "sequence": "additional",
      "affiliation": []
    },
    {
      "given": "Chih\u2010Shen",
      "family": "Tuan",
      "sequence": "additional",
      "affiliation": []
    },
    {
      "given": "Jen\u2010Lien",
      "family": "Lin",
      "sequence": "additional",
      "affiliation": []
    }
  ],
  "member": "311",
  "published-online": {
    "date-parts": [
      [
        2007,
        8,
        28
      ]
    ]
  },
  "reference": [
    {
      "key": "e_1_2_6_1_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1039/a902859e"
    },
    {
      "key": "e_1_2_6_2_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/cm9801439"
    },
    {
      "key": "e_1_2_6_3_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ma0100448"
    },
    {
      "key": "e_1_2_6_4_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/S0927-796X(00)00029-2"
    },
    {
      "key": "e_1_2_6_5_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ma051102i"
    },
    {
      "key": "e_1_2_6_6_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ma061861g"
    },
    {
      "key": "e_1_2_6_7_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1039/b203862e"
    },
    {
      "key": "e_1_2_6_8_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/macp.200600128"
    },
    {
      "key": "e_1_2_6_9_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/j.polymer.2005.11.058"
    },
    {
      "key": "e_1_2_6_10_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ma049204g"
    },
    {
      "key": "e_1_2_6_11_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ma048118d"
    },
    {
      "key": "e_1_2_6_12_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/polb.20997"
    },
    {
      "key": "e_1_2_6_13_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ma020405z"
    },
    {
      "key": "e_1_2_6_14_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1063/1.1406143"
    },
    {
      "key": "e_1_2_6_15_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1063/1.2713139"
    },
    {
      "key": "e_1_2_6_16_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1063/1.2142289"
    },
    {
      "key": "e_1_2_6_17_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/cm049825o"
    },
    {
      "key": "e_1_2_6_18_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/cm051561y"
    },
    {
      "key": "e_1_2_6_19_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/marc.200500616"
    },
    {
      "key": "e_1_2_6_20_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/marc.200500276"
    },
    {
      "key": "e_1_2_6_21_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/adfm.200305180"
    },
    {
      "key": "e_1_2_6_22_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/adma.200390030"
    },
    {
      "key": "e_1_2_6_23_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ma060421m"
    },
    {
      "key": "e_1_2_6_24_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/adma.200600124"
    },
    {
      "key": "e_1_2_6_25_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/marc.200600237"
    },
    {
      "key": "e_1_2_6_26_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/macp.200500517"
    },
    {
      "key": "e_1_2_6_27_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/cm050463"
    },
    {
      "key": "e_1_2_6_28_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1007/s00339-003-2498-5"
    },
    {
      "key": "e_1_2_6_29_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/adma.200304150"
    },
    {
      "key": "e_1_2_6_30_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1063/1.1825070"
    },
    {
      "key": "e_1_2_6_31_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/adfm.200500339"
    },
    {
      "key": "e_1_2_6_32_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/cm950467m"
    },
    {
      "key": "e_1_2_6_33_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1055/s-2002-32523"
    },
    {
      "key": "e_1_2_6_34_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ma00106a009"
    },
    {
      "key": "e_1_2_6_35_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/j.synthmet.2006.02.013"
    },
    {
      "key": "e_1_2_6_36_2",
      "first-page": "47",
      "author": "Wu W. C.",
      "year": "2006",
      "journal-title": "J. Polym. Res."
    },
    {
      "key": "e_1_2_6_37_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja039772w"
    },
    {
      "key": "e_1_2_6_38_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/cm049617w"
    },
    {
      "key": "e_1_2_6_39_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ma047415f"
    },
    {
      "key": "e_1_2_6_40_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1038/nmat1612"
    },
    {
      "key": "e_1_2_6_41_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/cm0008563"
    },
    {
      "key": "e_1_2_6_42_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/pola.21586"
    },
    {
      "key": "e_1_2_6_43_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1038/nature03376"
    }
  ],
  "container-title": "Macromolecular Chemistry and Physics",
  "original-title": [],
  "language": "en",
  "link": [
    {
      "URL": "https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fmacp.200700158",
      "content-type": "unspecified",
      "content-version": "vor",
      "intended-application": "text-mining"
    },
    {
      "URL": "https://onlinelibrary.wiley.com/doi/pdf/10.1002/macp.200700158",
      "content-type": "unspecified",
      "content-version": "vor",
      "intended-application": "similarity-checking"
    }
  ],
  "deposited": {
    "date-parts": [
      [
        2023,
        10,
        14
      ]
    ],
    "date-time": "2023-10-14T14:46:07Z",
    "timestamp": 1697294767000
  },
  "score": 1,
  "resource": {
    "primary": {
      "URL": "https://onlinelibrary.wiley.com/doi/10.1002/macp.200700158"
    }
  },
  "subtitle": [],
  "short-title": [],
  "issued": {
    "date-parts": [
      [
        2007,
        8,
        28
      ]
    ]
  },
  "references-count": 43,
  "journal-issue": {
    "issue": "17",
    "published-print": {
      "date-parts": [
        [
          2007,
          9,
          5
        ]
      ]
    }
  },
  "alternative-id": [
    "10.1002/macp.200700158"
  ],
  "URL": "http://dx.doi.org/10.1002/macp.200700158",
  "relation": {},
  "ISSN": [
    "1022-1352",
    "1521-3935"
  ],
  "subject": [],
  "container-title-short": "Macro Chemistry &amp; Physics",
  "published": {
    "date-parts": [
      [
        2007,
        8,
        28
      ]
    ]
  }
}