DOI: 10.1002/asia.201000506. Alternating and Diblock Donor–Acceptor Conjugated Polymers Based on Diindeno[1,2‐<i>b</i>:2′,1′‐<i>d</i>]thiophene Structure: Synthesis, Characterization, and Photovoltaic Applications

Alternating and Diblock Donor–Acceptor Conjugated Polymers Based on Diindeno[1,2‐b:2′,1′‐d]thiophene Structure: Synthesis, Characterization, and Photovoltaic Applications

10.1002/asia.201000506

Crossref journal-article

Wiley

Chemistry – An Asian Journal (311)

Abstract

AbstractPentacyclic diindeno[1,2‐b:2′,1′‐d]thiophene (DIDT) unit is a rigid and coplanar conjugated molecule. To the best of our knowledge, this attractive molecule has never been incorporated into a polymer and thus its application in polymer solar cells has never been explored. For the first time, we report the detailed synthesis of the tetra‐alkylated DIDT molecule leading to its dibromo‐ and diboronic ester derivatives, which are the key monomers for preparation of DIDT‐based polymers. Two donor–acceptor alternating polymers, poly(diindenothiophene‐alt‐benzothiadiazole) PDIDTBT and poly(diindenothiophene‐alt‐dithienylbenzothiadiazole) PDIDTDTBT, were synthesized by using Suzuki polymerization. Copolymer PTDIDTTBT was also prepared by using Stille polymerization. Although PTDIDTTBT is prepared through a manner of random polymerization, we found that the different reactivities of the dibromo‐monomers lead to the resulting polymer having a block copolymer arrangement. With the higher structural regularity, PTDIDTTBT, symbolized as (thiophene‐alt‐DIDT)0.5‐block‐(thiophene‐alt‐BT)0.5, shows the higher degree of crystallization, stronger π–π stacking, and broader absorption spectrum in the solid state, as compared to its alternating PDIDTDTBT analogue. Bulk heterojunction photovoltaic cells based on ITO/PEDOT:PSS/polymer:PC71BM/Ca/Al configuration were fabricated and characterized. PDIDTDTBT/PC71BM and PTDIDTTBT/PC71BM systems exhibited promising power‐conversion efficiencies (PCEs) of 1.65 % and 2.00 %, respectively. Owing to the complementary absorption spectra, as well as the compatible structures of PDIDTDTBT and PTDIDTTBT, the PCE of the device based on the ternary blend PDIDTDTBT/PTDIDTTBT/PC71BM was further improved to 2.40 %.

Bibliography

Chen, C., Cheng, Y., Dubosc, M., Hsieh, C., Chu, C., & Hsu, C. (2010). Alternating and Diblock DonorâAcceptor Conjugated Polymers Based on Diindeno[1,2âb:2â²,1â²âd]thiophene Structure: Synthesis, Characterization, and Photovoltaic Applications. Chemistry â An Asian Journal, 5(12), 2483â2492. Portico.

Authors 6

Chiu‐Hsiang Chen (first)
Yen‐Ju Cheng (additional)
Martin Dubosc (additional)
Chao‐Hsiang Hsieh (additional)
Cheng‐Che Chu (additional)
Chain‐Shu Hsu (additional)

References 74 Referenced 27

Dates

Type	When
Created	14 years, 10 months ago (Oct. 8, 2010, 10:23 a.m.)
Deposited	1 year, 10 months ago (Oct. 16, 2023, 4:20 p.m.)
Indexed	1 month ago (July 19, 2025, 11:40 p.m.)
Issued	14 years, 10 months ago (Oct. 8, 2010)
Published	14 years, 10 months ago (Oct. 8, 2010)
Published Online	14 years, 10 months ago (Oct. 8, 2010)
Published Print	14 years, 8 months ago (Dec. 3, 2010)

Funders 0

None

BibTeX

@article{Chen_2010, title={Alternating and Diblock Donor–Acceptor Conjugated Polymers Based on Diindeno[1,2‐b:2′,1′‐d]thiophene Structure: Synthesis, Characterization, and Photovoltaic Applications}, volume={5}, ISSN={1861-471X}, url={http://dx.doi.org/10.1002/asia.201000506}, DOI={10.1002/asia.201000506}, number={12}, journal={Chemistry – An Asian Journal}, publisher={Wiley}, author={Chen, Chiu‐Hsiang and Cheng, Yen‐Ju and Dubosc, Martin and Hsieh, Chao‐Hsiang and Chu, Cheng‐Che and Hsu, Chain‐Shu}, year={2010}, month=oct, pages={2483–2492} }

JSON

{
  "indexed": {
    "date-parts": [
      [
        2025,
        7,
        20
      ]
    ],
    "date-time": "2025-07-20T03:40:58Z",
    "timestamp": 1752982858183
  },
  "reference-count": 74,
  "publisher": "Wiley",
  "issue": "12",
  "license": [
    {
      "start": {
        "date-parts": [
          [
            2010,
            10,
            8
          ]
        ],
        "date-time": "2010-10-08T00:00:00Z",
        "timestamp": 1286496000000
      },
      "content-version": "vor",
      "delay-in-days": 0,
      "URL": "http://onlinelibrary.wiley.com/termsAndConditions#vor"
    }
  ],
  "content-domain": {
    "domain": [],
    "crossmark-restriction": false
  },
  "published-print": {
    "date-parts": [
      [
        2010,
        12,
        3
      ]
    ]
  },
  "abstract": "<jats:title>Abstract</jats:title><jats:p>Pentacyclic diindeno[1,2\u2010<jats:italic>b</jats:italic>:2\u2032,1\u2032\u2010<jats:italic>d</jats:italic>]thiophene (<jats:bold>DIDT</jats:bold>) unit is a rigid and coplanar conjugated molecule. To the best of our knowledge, this attractive molecule has never been incorporated into a polymer and thus its application in polymer solar cells has never been explored. For the first time, we report the detailed synthesis of the tetra\u2010alkylated <jats:bold>DIDT</jats:bold> molecule leading to its dibromo\u2010 and diboronic ester derivatives, which are the key monomers for preparation of <jats:bold>DIDT</jats:bold>\u2010based polymers. Two donor\u2013acceptor alternating polymers, poly(diindenothiophene\u2010<jats:italic>alt</jats:italic>\u2010benzothiadiazole) <jats:bold>PDIDTBT</jats:bold> and poly(diindenothiophene\u2010<jats:italic>alt</jats:italic>\u2010dithienylbenzothiadiazole) <jats:bold>PDIDTDTBT</jats:bold>, were synthesized by using Suzuki polymerization. Copolymer <jats:bold>PTDIDTTBT</jats:bold> was also prepared by using Stille polymerization. Although <jats:bold>PTDIDTTBT</jats:bold> is prepared through a manner of random polymerization, we found that the different reactivities of the dibromo\u2010monomers lead to the resulting polymer having a block copolymer arrangement. With the higher structural regularity, <jats:bold>PTDIDTTBT</jats:bold>, symbolized as (thiophene\u2010<jats:italic>alt</jats:italic>\u2010<jats:bold>DIDT</jats:bold>)<jats:sub>0.5</jats:sub>\u2010<jats:italic>block</jats:italic>\u2010(thiophene\u2010<jats:italic>alt</jats:italic>\u2010BT)<jats:sub>0.5</jats:sub>, shows the higher degree of crystallization, stronger \u03c0\u2013\u03c0 stacking, and broader absorption spectrum in the solid state, as compared to its alternating <jats:bold>PDIDTDTBT</jats:bold> analogue. Bulk heterojunction photovoltaic cells based on ITO/PEDOT:PSS/polymer:PC<jats:sub>71</jats:sub>BM/Ca/Al configuration were fabricated and characterized. <jats:bold>PDIDTDTBT</jats:bold>/PC<jats:sub>71</jats:sub>BM and <jats:bold>PTDIDTTBT</jats:bold>/PC<jats:sub>71</jats:sub>BM systems exhibited promising power\u2010conversion efficiencies (PCEs) of 1.65\u2009% and 2.00\u2009%, respectively. Owing to the complementary absorption spectra, as well as the compatible structures of <jats:bold>PDIDTDTBT</jats:bold> and <jats:bold>PTDIDTTBT</jats:bold>, the PCE of the device based on the ternary blend <jats:bold>PDIDTDTBT</jats:bold>/<jats:bold>PTDIDTTBT</jats:bold>/PC<jats:sub>71</jats:sub>BM was further improved to 2.40\u2009%.</jats:p>",
  "DOI": "10.1002/asia.201000506",
  "type": "journal-article",
  "created": {
    "date-parts": [
      [
        2010,
        10,
        8
      ]
    ],
    "date-time": "2010-10-08T14:23:33Z",
    "timestamp": 1286547813000
  },
  "page": "2483-2492",
  "source": "Crossref",
  "is-referenced-by-count": 27,
  "title": "Alternating and Diblock Donor\u2013Acceptor Conjugated Polymers Based on Diindeno[1,2\u2010<i>b</i>:2\u2032,1\u2032\u2010<i>d</i>]thiophene Structure: Synthesis, Characterization, and Photovoltaic Applications",
  "prefix": "10.1002",
  "volume": "5",
  "author": [
    {
      "given": "Chiu\u2010Hsiang",
      "family": "Chen",
      "sequence": "first",
      "affiliation": []
    },
    {
      "given": "Yen\u2010Ju",
      "family": "Cheng",
      "sequence": "additional",
      "affiliation": []
    },
    {
      "given": "Martin",
      "family": "Dubosc",
      "sequence": "additional",
      "affiliation": []
    },
    {
      "given": "Chao\u2010Hsiang",
      "family": "Hsieh",
      "sequence": "additional",
      "affiliation": []
    },
    {
      "given": "Cheng\u2010Che",
      "family": "Chu",
      "sequence": "additional",
      "affiliation": []
    },
    {
      "given": "Chain\u2010Shu",
      "family": "Hsu",
      "sequence": "additional",
      "affiliation": []
    }
  ],
  "member": "311",
  "published-online": {
    "date-parts": [
      [
        2010,
        10,
        8
      ]
    ]
  },
  "reference": [
    {
      "key": "e_1_2_6_1_2",
      "unstructured": "\u00a0"
    },
    {
      "key": "e_1_2_6_2_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1126/science.270.5243.1789"
    },
    {
      "key": "e_1_2_6_3_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/cr050149z"
    },
    {
      "key": "e_1_2_6_4_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/ange.200702506"
    },
    {
      "key": "e_1_2_6_4_3",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/anie.200702506"
    },
    {
      "key": "e_1_2_6_5_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/cr900182s"
    },
    {
      "key": "e_1_2_6_6_2",
      "unstructured": "\u00a0"
    },
    {
      "key": "e_1_2_6_7_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/cr950257t"
    },
    {
      "key": "e_1_2_6_8_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/S0927-796X(00)00029-2"
    },
    {
      "key": "e_1_2_6_9_2",
      "unstructured": "\u00a0"
    },
    {
      "key": "e_1_2_6_10_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja909111p"
    },
    {
      "key": "e_1_2_6_11_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1039/c003040f"
    },
    {
      "key": "e_1_2_6_12_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/adma.200903528"
    },
    {
      "key": "e_1_2_6_13_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/ange.200906934"
    },
    {
      "key": "e_1_2_6_13_3",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/anie.200906934"
    },
    {
      "key": "e_1_2_6_14_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ma9025866"
    },
    {
      "key": "e_1_2_6_15_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/adma.200602496"
    },
    {
      "key": "e_1_2_6_16_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ma802052w"
    },
    {
      "key": "e_1_2_6_17_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja806687u"
    },
    {
      "key": "e_1_2_6_18_2",
      "unstructured": "\u00a0"
    },
    {
      "key": "e_1_2_6_19_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/adma.200304150"
    },
    {
      "key": "e_1_2_6_20_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1063/1.1667614"
    },
    {
      "key": "e_1_2_6_21_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/adfm.200400416"
    },
    {
      "key": "e_1_2_6_22_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/adma.200600124"
    },
    {
      "key": "e_1_2_6_23_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1063/1.2718488"
    },
    {
      "key": "e_1_2_6_24_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1039/b811957k"
    },
    {
      "key": "e_1_2_6_25_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1063/1.3070574"
    },
    {
      "key": "e_1_2_6_26_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja9066139"
    },
    {
      "key": "e_1_2_6_27_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1039/b412143k"
    },
    {
      "key": "e_1_2_6_28_2",
      "unstructured": "\u00a0"
    },
    {
      "key": "e_1_2_6_29_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ma062376o"
    },
    {
      "key": "e_1_2_6_30_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/adma.200600160"
    },
    {
      "key": "e_1_2_6_31_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1126/science.1141711"
    },
    {
      "key": "e_1_2_6_32_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1038/nmat1928"
    },
    {
      "key": "e_1_2_6_33_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/marc.200700345"
    },
    {
      "key": "e_1_2_6_34_2",
      "unstructured": "\u00a0"
    },
    {
      "key": "e_1_2_6_35_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1073/pnas.092143399"
    },
    {
      "key": "e_1_2_6_36_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja042219"
    },
    {
      "key": "e_1_2_6_37_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/cm8016424"
    },
    {
      "key": "e_1_2_6_38_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja808373p"
    },
    {
      "key": "e_1_2_6_39_2",
      "unstructured": "\u00a0"
    },
    {
      "key": "e_1_2_6_40_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ol061791y"
    },
    {
      "key": "e_1_2_6_41_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ma800494k"
    },
    {
      "key": "e_1_2_6_42_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja801877k"
    },
    {
      "key": "e_1_2_6_43_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/cm9007798"
    },
    {
      "key": "e_1_2_6_44_2",
      "unstructured": "\u00a0"
    },
    {
      "key": "e_1_2_6_45_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/cber.19881211219"
    },
    {
      "key": "e_1_2_6_46_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/adma.19940061108"
    },
    {
      "key": "e_1_2_6_47_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/jo902482n"
    },
    {
      "key": "e_1_2_6_48_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1107/S1600536807063684"
    },
    {
      "key": "e_1_2_6_49_2",
      "unstructured": "\u00a0"
    },
    {
      "key": "e_1_2_6_50_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja0002058"
    },
    {
      "key": "e_1_2_6_51_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/om0604932"
    },
    {
      "key": "e_1_2_6_52_2",
      "unstructured": "\u00a0"
    },
    {
      "key": "e_1_2_6_53_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1039/b203862e"
    },
    {
      "key": "e_1_2_6_54_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/cm800955f"
    },
    {
      "key": "e_1_2_6_55_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja060141m"
    },
    {
      "key": "e_1_2_6_56_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/adma.200800606"
    },
    {
      "key": "e_1_2_6_57_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ma062633p"
    },
    {
      "key": "e_1_2_6_58_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/jp711623w"
    },
    {
      "key": "e_1_2_6_59_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ma060662u"
    },
    {
      "key": "e_1_2_6_60_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/jp7105428"
    },
    {
      "key": "e_1_2_6_61_2",
      "unstructured": "\u00a0"
    },
    {
      "key": "e_1_2_6_62_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/pip.788"
    },
    {
      "key": "e_1_2_6_63_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1039/B301403G"
    },
    {
      "key": "e_1_2_6_64_2",
      "unstructured": "\u00a0"
    },
    {
      "key": "e_1_2_6_65_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/ange.200351647"
    },
    {
      "key": "e_1_2_6_65_3",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/anie.200351647"
    },
    {
      "key": "e_1_2_6_66_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1063/1.2361082"
    },
    {
      "key": "e_1_2_6_67_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ma902206u"
    },
    {
      "key": "e_1_2_6_68_2",
      "unstructured": "\u00a0"
    },
    {
      "key": "e_1_2_6_69_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1039/B510618B"
    },
    {
      "key": "e_1_2_6_70_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/1616-3028(200112)11:6<420::AID-ADFM420>3.0.CO;2-K"
    },
    {
      "key": "e_1_2_6_71_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ar7002539"
    }
  ],
  "container-title": "Chemistry \u2013 An Asian Journal",
  "original-title": [],
  "language": "en",
  "link": [
    {
      "URL": "https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fasia.201000506",
      "content-type": "unspecified",
      "content-version": "vor",
      "intended-application": "text-mining"
    },
    {
      "URL": "https://onlinelibrary.wiley.com/doi/pdf/10.1002/asia.201000506",
      "content-type": "unspecified",
      "content-version": "vor",
      "intended-application": "similarity-checking"
    }
  ],
  "deposited": {
    "date-parts": [
      [
        2023,
        10,
        16
      ]
    ],
    "date-time": "2023-10-16T20:20:17Z",
    "timestamp": 1697487617000
  },
  "score": 1,
  "resource": {
    "primary": {
      "URL": "https://onlinelibrary.wiley.com/doi/10.1002/asia.201000506"
    }
  },
  "subtitle": [],
  "short-title": [],
  "issued": {
    "date-parts": [
      [
        2010,
        10,
        8
      ]
    ]
  },
  "references-count": 74,
  "journal-issue": {
    "issue": "12",
    "published-print": {
      "date-parts": [
        [
          2010,
          12,
          3
        ]
      ]
    }
  },
  "alternative-id": [
    "10.1002/asia.201000506"
  ],
  "URL": "http://dx.doi.org/10.1002/asia.201000506",
  "relation": {},
  "ISSN": [
    "1861-4728",
    "1861-471X"
  ],
  "subject": [],
  "container-title-short": "Chemistry \u0097 An Asian Journal",
  "published": {
    "date-parts": [
      [
        2010,
        10,
        8
      ]
    ]
  }
}