Investigation of hydrogen-bonding mediated molecular packing of diketopyrrolopyrrole based donor-acceptor oligomers in the solid state
Investigation of hydrogen-bonding mediated molecular packing of diketopyrrolopyrrole based donor-acceptor oligomers in the solid state
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DOI：
10.1016/j.polymer.2018.11.029
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发表时间：
2019-01
期刊：
影响因子：
4.6
通讯作者：
Kun Yang;Xiang Li;Yi-Fan Huang;R. Bhatta;Jiawei Liu;M. Tsige;Chien-Lung Wang;Stephen Z. D. Cheng;Yu Zhu
中科院分区：
文献类型：
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作者：
Kun Yang;Xiang Li;Yi-Fan Huang;R. Bhatta;Jiawei Liu;M. Tsige;Chien-Lung Wang;Stephen Z. D. Cheng;Yu Zhu
合成并表征了两种具有热不稳定 2-甲基己基-2-氧基羰基 (mHoc) 基团的二酮吡咯并吡咯 (DPP) 供体-受体低聚物 mHocPBT 和 mHocTBT，以研究固态氢键介导的分子堆积。通过在 180 至 200°C 的温度下对流延固体薄膜进行退火，可溶性低聚物可转化为强分子间氢键和颜料状材料 HPBT 和 HTBT。分子间氢键的形成显着改变了低聚物的分子构象、分子堆积结构和相关光学性质，HPBT分子在紫外/可见光谱上表现出红移，HTBT分子表现出红移。旋涂 mHocTBT 和 HTBT 薄膜还表现出有趣的形态和电荷传输特性。尽管单个mHocTBT低聚物分子与HTBT相比具有更好的共面分子构象，但增强的π-π堆叠结构和更大的晶粒尺寸使HTBT薄膜具有更好的电荷传输性能。
Two diketopyrrolopyrrole (DPP)-based donor-acceptor oligomers with thermal labile 2-methylhexyl-2-oxylcarbonyl (mHoc) groups, mHocPBT and mHocTBT, were synthesized and characterized to study the hydrogen-bonding mediated molecular packing in solid state. The soluble oligomers can be converted to strong intermolecular hydrogen-bonded and pigment-like materials HPBT and HTBT by annealing the casted solid film at a temperature between 180 and 200 °C. The formation of intermolecular hydrogen bonding significantly altered the conformation of the molecules, molecular packing structure and related optical properties of the oligomers, with HPBT molecule exhibiting bathochromic shift and HTBT molecule exhibiting hypsochromic shift on UV/Vis spectra. Spin-casted mHocTBT and HTBT films also exhibited interesting morphology and charge transport properties. Even though the single mHocTBT oligomer molecule has a better coplanar molecular conformation as compared with that of HTBT, an enhanced π-π stacking structure and larger crystal grain size rendered HTBT film better charge transport performance.