Synthesis and Aggregation Behavior of a Glycolated Naphthalene Diimide Bithiophene Copolymer for Application in Low-Level n-Doped Organic Thermoelectrics Article Swipe
Younghun Shin
,
Hartmut Komber
,
Davide Caiola
,
Marco Cassinelli
,
Hengda Sun
,
Dominik Stegerer
,
Marcel Schreiter
,
K Horatz
,
Franziska Lissel
,
Xuechen Jiao
,
Christopher R. McNeill
,
Simone Cimò
,
Chiara Bertarelli
,
Simone Fabiano
,
Mario Caironi
,
Michael Sommer
·
YOU?
·
· 2020
· Open Access
·
· DOI: https://doi.org/10.1021/acs.macromol.0c00657
YOU?
·
· 2020
· Open Access
·
· DOI: https://doi.org/10.1021/acs.macromol.0c00657
The synthesis of a naphthalene diimide bithiophene copolymer P(EO-NDIT2) with branched, base-stable, and purely ether-based side chains is presented. Stille polycondensation leads to high molecular weights that are limited by methyl transfer and eventually T2 homocouplings. While extensive solution aggregation hampers molecular weight determination by conventional methods, NMR spectroscopy allows identification of both T2- (H and methyl) and NDI-related (methyl) end groups, enabling the determination of absolute number average molecular weights larger than Mn,NMR ∼100 kg/mol. Solvent- and temperature-dependent aggregation in solution is investigated by NMR and UV-vis spectroscopy. These results are used for solution doping of P(EO-NDIT2) with N-benzimidazole-based n-dopants. Spin coating from heated chlorobenzene solutions and using 4-(2,3-dihydro-1,3-dimethyl-1H-benzoimidazol-2-yl)-N,N-diisopropylaniline (N-DiPrBI) as the dopant leads to homogeneous films with highest conductivities up to 10-2 S/cm. Generally, N-DiPrBI concentrations as low as ∼5 wt % are sufficient to increase conductivity by orders of magnitude. Strikingly, maximum power factors up to 0.11 μW/mK2, although limited by conductivity, are achieved for the highest molar mass sample at a low dopant concentration of 2 wt % N-DiPrBI only.
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- Type
- article
- Language
- en
- Landing Page
- https://doi.org/10.1021/acs.macromol.0c00657
- OA Status
- green
- Cited By
- 32
- References
- 44
- Related Works
- 10
- OpenAlex ID
- https://openalex.org/W3038242232
All OpenAlex metadata
Raw OpenAlex JSON
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https://openalex.org/W3038242232Canonical identifier for this work in OpenAlex
- DOI
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https://doi.org/10.1021/acs.macromol.0c00657Digital Object Identifier
- Title
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Synthesis and Aggregation Behavior of a Glycolated Naphthalene Diimide Bithiophene Copolymer for Application in Low-Level n-Doped Organic ThermoelectricsWork title
- Type
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articleOpenAlex work type
- Language
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enPrimary language
- Publication year
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2020Year of publication
- Publication date
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2020-07-01Full publication date if available
- Authors
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Younghun Shin, Hartmut Komber, Davide Caiola, Marco Cassinelli, Hengda Sun, Dominik Stegerer, Marcel Schreiter, K Horatz, Franziska Lissel, Xuechen Jiao, Christopher R. McNeill, Simone Cimò, Chiara Bertarelli, Simone Fabiano, Mario Caironi, Michael SommerList of authors in order
- Landing page
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https://doi.org/10.1021/acs.macromol.0c00657Publisher landing page
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YesWhether a free full text is available
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greenOpen access status per OpenAlex
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https://hdl.handle.net/11311/1159324Direct OA link when available
- Concepts
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Copolymer, Naphthalene, Doping, Chemical engineering, Diimide, Polymer chemistry, Materials science, Chemistry, Organic chemistry, Photochemistry, Polymer, Perylene, Molecule, Optoelectronics, EngineeringTop concepts (fields/topics) attached by OpenAlex
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32Total citation count in OpenAlex
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2025: 2, 2024: 2, 2023: 5, 2022: 9, 2021: 14Per-year citation counts (last 5 years)
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44Number of works referenced by this work
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10Other works algorithmically related by OpenAlex
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| abstract_inverted_index.that | 26 |
| abstract_inverted_index.used | 92 |
| abstract_inverted_index.with | 9, 98, 118 |
| abstract_inverted_index.∼5 | 131 |
| abstract_inverted_index.S/cm. | 124 |
| abstract_inverted_index.These | 89 |
| abstract_inverted_index.While | 36 |
| abstract_inverted_index.films | 117 |
| abstract_inverted_index.leads | 21, 114 |
| abstract_inverted_index.molar | 160 |
| abstract_inverted_index.only. | 173 |
| abstract_inverted_index.power | 145 |
| abstract_inverted_index.using | 108 |
| abstract_inverted_index.Mn,NMR | 73 |
| abstract_inverted_index.Stille | 19 |
| abstract_inverted_index.UV-vis | 87 |
| abstract_inverted_index.allows | 49 |
| abstract_inverted_index.chains | 16 |
| abstract_inverted_index.dopant | 113, 166 |
| abstract_inverted_index.doping | 95 |
| abstract_inverted_index.heated | 104 |
| abstract_inverted_index.larger | 71 |
| abstract_inverted_index.methyl | 30 |
| abstract_inverted_index.number | 67 |
| abstract_inverted_index.orders | 140 |
| abstract_inverted_index.purely | 13 |
| abstract_inverted_index.sample | 162 |
| abstract_inverted_index.weight | 42 |
| abstract_inverted_index.∼100 | 74 |
| abstract_inverted_index.average | 68 |
| abstract_inverted_index.coating | 102 |
| abstract_inverted_index.diimide | 5 |
| abstract_inverted_index.factors | 146 |
| abstract_inverted_index.groups, | 61 |
| abstract_inverted_index.hampers | 40 |
| abstract_inverted_index.highest | 119, 159 |
| abstract_inverted_index.kg/mol. | 75 |
| abstract_inverted_index.limited | 28, 152 |
| abstract_inverted_index.maximum | 144 |
| abstract_inverted_index.methyl) | 56 |
| abstract_inverted_index.results | 90 |
| abstract_inverted_index.weights | 25, 70 |
| abstract_inverted_index.(methyl) | 59 |
| abstract_inverted_index.N-DiPrBI | 126, 172 |
| abstract_inverted_index.Solvent- | 76 |
| abstract_inverted_index.absolute | 66 |
| abstract_inverted_index.achieved | 156 |
| abstract_inverted_index.although | 151 |
| abstract_inverted_index.enabling | 62 |
| abstract_inverted_index.increase | 137 |
| abstract_inverted_index.methods, | 46 |
| abstract_inverted_index.solution | 38, 81, 94 |
| abstract_inverted_index.transfer | 31 |
| abstract_inverted_index.μW/mK2, | 150 |
| abstract_inverted_index.branched, | 10 |
| abstract_inverted_index.copolymer | 7 |
| abstract_inverted_index.extensive | 37 |
| abstract_inverted_index.molecular | 24, 41, 69 |
| abstract_inverted_index.solutions | 106 |
| abstract_inverted_index.synthesis | 1 |
| abstract_inverted_index.(N-DiPrBI) | 110 |
| abstract_inverted_index.Generally, | 125 |
| abstract_inverted_index.eventually | 33 |
| abstract_inverted_index.magnitude. | 142 |
| abstract_inverted_index.n-dopants. | 100 |
| abstract_inverted_index.presented. | 18 |
| abstract_inverted_index.sufficient | 135 |
| abstract_inverted_index.NDI-related | 58 |
| abstract_inverted_index.P(EO-NDIT2) | 8, 97 |
| abstract_inverted_index.Strikingly, | 143 |
| abstract_inverted_index.aggregation | 39, 79 |
| abstract_inverted_index.bithiophene | 6 |
| abstract_inverted_index.ether-based | 14 |
| abstract_inverted_index.homogeneous | 116 |
| abstract_inverted_index.naphthalene | 4 |
| abstract_inverted_index.base-stable, | 11 |
| abstract_inverted_index.conductivity | 138 |
| abstract_inverted_index.conventional | 45 |
| abstract_inverted_index.investigated | 83 |
| abstract_inverted_index.spectroscopy | 48 |
| abstract_inverted_index.chlorobenzene | 105 |
| abstract_inverted_index.concentration | 167 |
| abstract_inverted_index.conductivity, | 154 |
| abstract_inverted_index.determination | 43, 64 |
| abstract_inverted_index.spectroscopy. | 88 |
| abstract_inverted_index.concentrations | 127 |
| abstract_inverted_index.conductivities | 120 |
| abstract_inverted_index.homocouplings. | 35 |
| abstract_inverted_index.identification | 50 |
| abstract_inverted_index.polycondensation | 20 |
| abstract_inverted_index.N-benzimidazole-based | 99 |
| abstract_inverted_index.temperature-dependent | 78 |
| abstract_inverted_index.4-(2,3-dihydro-1,3-dimethyl-1H-benzoimidazol-2-yl)-N,N-diisopropylaniline | 109 |
| cited_by_percentile_year.max | 99 |
| cited_by_percentile_year.min | 94 |
| corresponding_author_ids | https://openalex.org/A5048875966 |
| countries_distinct_count | 4 |
| institutions_distinct_count | 16 |
| corresponding_institution_ids | https://openalex.org/I2610724 |
| sustainable_development_goals[0].id | https://metadata.un.org/sdg/6 |
| sustainable_development_goals[0].score | 0.6399999856948853 |
| sustainable_development_goals[0].display_name | Clean water and sanitation |
| citation_normalized_percentile.value | 0.90541536 |
| citation_normalized_percentile.is_in_top_1_percent | False |
| citation_normalized_percentile.is_in_top_10_percent | True |