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Synthesis and Aggregation Behavior of a Glycolated Naphthalene Diimide Bithiophene Copolymer for Application in Low-Level n-Doped Organic Thermoelectrics
Macromolecules ( IF 5.1 ) Pub Date : 2020-07-01 , DOI: 10.1021/acs.macromol.0c00657 Young-hun Shin 1 , Hartmut Komber 2 , Davide Caiola 3 , Marco Cassinelli 3 , Hengda Sun 4 , Dominik Stegerer 1 , Marcel Schreiter 1 , Kilian Horatz 2 , Franziska Lissel 2, 5 , Xuechen Jiao 6 , Christopher R. McNeill 6 , Simone Cimò 3, 7 , Chiara Bertarelli 3, 7 , Simone Fabiano 4 , Mario Caironi 3 , Michael Sommer 1
Macromolecules ( IF 5.1 ) Pub Date : 2020-07-01 , DOI: 10.1021/acs.macromol.0c00657 Young-hun Shin 1 , Hartmut Komber 2 , Davide Caiola 3 , Marco Cassinelli 3 , Hengda Sun 4 , Dominik Stegerer 1 , Marcel Schreiter 1 , Kilian Horatz 2 , Franziska Lissel 2, 5 , Xuechen Jiao 6 , Christopher R. McNeill 6 , Simone Cimò 3, 7 , Chiara Bertarelli 3, 7 , Simone Fabiano 4 , Mario Caironi 3 , Michael Sommer 1
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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.
中文翻译：
糖基化萘二酰亚胺联噻吩共聚物的合成及聚集行为在低水平n掺杂有机热电中的应用
提出了带有支链，碱稳定和纯醚基侧链的萘二酰亚胺联噻吩共聚物P（EO-NDIT2）的合成。斯蒂勒缩聚反应导致高分子量，该分子量受到甲基转移和最终的T2均偶联作用的限制。虽然广泛的溶液聚集会妨碍通过常规方法测定分子量，但NMR光谱法可识别T2-（H和甲基）和NDI相关的（甲基）端基，从而能够确定大于M n的绝对数均分子量约100千克/摩尔 通过NMR和UV-vis光谱研究溶液中与溶剂和温度有关的聚集。这些结果用于基于N-苯并咪唑的n-掺杂剂对P（EO-NDIT2）的溶液掺杂。从加热的氯苯溶液中旋涂，并使用4-（2,3-二氢-1,3-二甲基-1 H-苯并咪唑-2-基）-N，N-二异丙基苯胺（N-DiPrBI）作为掺杂剂，可得到均匀的薄膜电导率最高，可达10 –2 S / cm。通常，低至约5 wt％的N-DiPrBI浓度足以将电导率提高几个数量级。惊人的是，最大功率因数高达0.11μW/ mK 2尽管受电导率的限制，但对于仅2 wt％N-DiPrBI的低掺杂物浓度的最高摩尔质量的样品，却可以达到。
更新日期：2020-07-14
中文翻译：
糖基化萘二酰亚胺联噻吩共聚物的合成及聚集行为在低水平n掺杂有机热电中的应用
提出了带有支链，碱稳定和纯醚基侧链的萘二酰亚胺联噻吩共聚物P（EO-NDIT2）的合成。斯蒂勒缩聚反应导致高分子量，该分子量受到甲基转移和最终的T2均偶联作用的限制。虽然广泛的溶液聚集会妨碍通过常规方法测定分子量，但NMR光谱法可识别T2-（H和甲基）和NDI相关的（甲基）端基，从而能够确定大于M n的绝对数均分子量约100千克/摩尔 通过NMR和UV-vis光谱研究溶液中与溶剂和温度有关的聚集。这些结果用于基于N-苯并咪唑的n-掺杂剂对P（EO-NDIT2）的溶液掺杂。从加热的氯苯溶液中旋涂，并使用4-（2,3-二氢-1,3-二甲基-1 H-苯并咪唑-2-基）-N，N-二异丙基苯胺（N-DiPrBI）作为掺杂剂，可得到均匀的薄膜电导率最高，可达10 –2 S / cm。通常，低至约5 wt％的N-DiPrBI浓度足以将电导率提高几个数量级。惊人的是，最大功率因数高达0.11μW/ mK 2尽管受电导率的限制，但对于仅2 wt％N-DiPrBI的低掺杂物浓度的最高摩尔质量的样品，却可以达到。
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