Oligo- and Poly(fullerene)s for Photovoltaic Applications: Modeled Electronic Behaviors and Synthesis
Oligo- and Poly(fullerene)s for Photovoltaic Applications: Modeled Electronic Behaviors and Synthesis
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DOI：
10.1002/pola.28502
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发表时间：
2017-04
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通讯作者：
H. S. Silva;Hasina H Ramanitra;B. Bregadiolli;D. Bégué;C. Graeff;Christine Dagron-Lartigau;H. Peisert;T. Chassé;R. Hiorns
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作者：
H. S. Silva;Hasina H Ramanitra;B. Bregadiolli;D. Bégué;C. Graeff;Christine Dagron-Lartigau;H. Peisert;T. Chassé;R. Hiorns
探索了富勒烯的原子转移自由基加成聚合（ATRAP）以产生用于有机电子产品的聚（富勒烯）（PF）。量子化学绘制了 PF 相对于常见电子受体（即富勒烯、苯基-C61-丁酸甲酯及其双加合物，以及单和双茚富勒烯衍生物）的预期电子行为。令人惊讶的是，我们发现 PF 应该表现出比单加合物更接近双衍生物的电子亲和力和 LUMO 能级，即使在 PF 链形成中仅使用一个 C60 双键。合成了一个自洽的 PF 库，并发现了结构特征和分子量之间的相关性。虽然具有 –OC16H33 线性侧链的共聚单体导致已知的最高 ATRAP 分子量为 21000 g mol−1，但类似的支化侧链允许合成更高分子量和更易溶解的聚合物。然而，在该系列中，具有 -OC12 侧链的 PF 由于其易于处理和最高的区域规整性，预计将最受光电应用的关注。 © 2017 Wiley periodicals, Inc. J. Polym。科学，A 部分：聚合物。化学。 2017年
The atom transfer radical addition polymerization (ATRAP) of fullerene to give poly(fullerene)s (PFs) for organic electronics is explored. Quantum chemistry maps the expected electronic behavior of PFs with respect to common electron acceptors, namely fullerene, phenyl-C61-butyric acid methyl ester and its bis-adduct, and mono- and bis-indine-fullerene derivatives. Surprisingly, it is found that PFs should demonstrate electron affinities and LUMO energy levels closer to the bis-derivatives than the mono-adducts, even though only one C60 double-bond is used in PF chain formation. A self-consistent library of PFs is synthesized and a correlation between structural characteristics and molecular weights is found. While comonomers with –OC16H33 linear side-chains lead to the highest known ATRAP molecular weights of 21000 g mol−1, like-for-like, branched side-chains permit syntheses of higher molecular weights and more soluble polymers. Of the series, however, PFs with -OC12 side-chains are expected to be of the greatest interest for opto-electronic applications due to their ease of handling and highest regioregularity. © 2017 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2017