Stereoregular pendant electroactive polymers with extended pendants via post-polymerization copper catalyzed azide-alkyne cycloaddition

IF 2.702 Q1 Materials Science Journal of Polymer Science Part A: Polymer Chemistry Pub Date : 2023-06-16 DOI:10.1002/pol.20230294
Alexander Schmitt, Qingpei Wan, Barry C. Thompson
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Abstract

Recent work on non-conjugated pendant electroactive polymers (NCPEPs) has demonstrated significant impacts of structural parameters such as backbone stereoregularity and the spacer connecting the pendant to the backbone on properties, most notably on charge carrier mobilities. Tuning of the pendant group however has not been reported for stereoregular NCPEPs. Here we present a family of novel isotactic poly((carbazolyl-alkyl-triazolyl)methyl methacrylates) (PCzATMMAs) for which the effects of increasing the pendant group from carbazole to 3,6-bis(4-(2-ethylhexyl)thiophen-2-yl)-carbazole were investigated. Based on unsuccessful post-polymerization functionalization with this extended group via previously reported transesterification and thiol-ene methodologies, we report functionalization via copper-catalyzed azide-alkyne cycloaddition which was demonstrated to be highly effective. The effect of spacer length was also investigated for comparison with previously established effects with alkyl spacers. Within the family of PCzATMMAs, hole mobilities were found to increase with longer spacer length and with thermal annealing. The incorporation of an extended pendant with alkyl solubilizing chains was found to result in a lower hole mobility than the equivalent polymer with an unfunctionalized pendant group. Importantly, the copper catalyzed azide-alkyne cycloaddition proved to be an effective method of post-polymerization functionalization for stereoregular NCPEPs when extending beyond a simple carbazole pendant.

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通过铜催化叠氮化物-炔环加成制备具有延伸垂链的立体规则垂链电活性聚合物
最近对非共轭垂链电活性聚合物(NCPEPs)的研究表明,结构参数(如主链的立体规则性和连接垂链与主链的间隔层)对其性能有显著影响,尤其是对载流子迁移率的影响。然而,对于立体规则的ncpep,尚未报道吊坠组的调谐。本文研究了一类新型等规聚((咔唑基-烷基-三唑基)甲基丙烯酸甲酯(PCzATMMAs),研究了将咔唑的悬垂基团增加到3,6-二(4-(2-乙基己基)噻吩-2-基)咔唑的效果。基于先前报道的通过酯交换和巯基方法不成功的聚合后官能化,我们报道了通过铜催化叠氮-炔环加成的官能化,这被证明是非常有效的。还研究了间隔长度的影响,并与先前建立的烷基间隔效果进行了比较。在pczatmma家族中,孔迁移率随间隔长度的增加和热退火的增加而增加。与具有烷基增溶链的延伸垂链相比,具有非官能化垂链的等效聚合物具有更低的空穴迁移率。重要的是,铜催化叠氮化物-炔环加成被证明是一种有效的聚合后功能化方法,当延伸到一个简单的咔唑垂链时。
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来源期刊
CiteScore
5.20
自引率
0.00%
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0
审稿时长
1.8 months
期刊介绍: Part A: Polymer Chemistry is devoted to studies in fundamental organic polymer chemistry and physical organic chemistry. This includes all related topics (such as organic, bioorganic, bioinorganic and biological chemistry of monomers, polymers, oligomers and model compounds, inorganic and organometallic chemistry for catalysts, mechanistic studies, supramolecular chemistry aspects relevant to polymer...
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Issue Information - Cover Description Cover Image, Volume 61, Issue 20 Issue Information - Cover Description Cover Image, Volume 61, Issue 19 Emerging researchers interview—Ji Liu, Southern University of Science and Technology
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