Synthesis, Self-Assembly and Characterization of Tandem Triblock BPOSS-PDI-X Shape Amphiphiles
Synthesis, Self-Assembly and Characterization of Tandem Triblock BPOSS-PDI-X Shape Amphiphiles
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串联三嵌段 BPOSS-PDI-X 形状两亲物的合成、自组装和表征
DOI：
10.3390/molecules24112114
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发表时间：
2019-06
期刊：
影响因子：
4.6
通讯作者：
Zhu Meifang
中科院分区：
文献类型：
--
作者：
Shao Yu;Chen Jia;Ren Xiang Kui;Zhang Xinlin;Yin Guang Zhong;Li Xiaopeng;Wang Jing;Wesdemiotis Chrys;Zhang Wen-Bin;Yang Shuguang;Sun Bin;Zhu Meifang
本文报道了基于异丁基官能化的笼型倍半硅氧烷（BPOSS）、二萘嵌苯四羧酸二酰亚胺（PDI）和富勒烯（C60）的形状两亲物（BPOSS-PDI-X）的合成、自组装和表征。首先，以苝-3，4，9，10-四甲酸二酐和两种不同的胺BPOSS-NH 2和3-氨基-1-丙醇为原料，通过一锅法反应得到了功能化的两嵌段两亲物前体（BPOSS-PDI-OH）。进一步与C60-COOH偶联得到三嵌段两亲物（BPOSS-PDI-C60）。通过NMR、IR和MALDI-TOF MS对其结构进行了表征。为了深入了解其结构与性能的关系，分别采用行波离子迁移质谱（TWIM-MS）、紫外/维斯吸收光谱、荧光发射光谱和透射电子显微镜对它们在气相、溶液和固态中的自组装进行了表征。发现BPOSS-PDI-OH形成比BPOSS-PDI-C60更复杂的二聚体。这两种样品在溶液中均表现出独特的聚集行为，并随浓度的增加而增加，这既不能归因于H-也不能归因于J-型，而可能与离散的二聚体有关。BPOSS-PDI-C60很难形成有序结构，而BPOSS-PDI-OH可以形成纳米带状的单晶，这在微电子领域具有潜在的应用价值。
In this article, we report the facile synthesis, self-assembly, and characterization of shape amphiphiles (BPOSS-PDI-X) based on isobutyl-functionalized polyhedral oligomeric silsesquioxane (BPOSS), perylene tetracarboxylic diimide (PDI), and (60)fullerene (C60) moieties. Firstly, an asymmetrically functionalized diblock shape amphiphile precursor (BPOSS-PDI-OH) was obtained through the one-pot reaction between perylene-3,4,9,10-tetracarboxylic dianhydride and two different amines, namely BPOSS-NH2 and 3-amino-1-propanol. It was further conjugated with C60-COOH to give a tri-block shape amphiphile (BPOSS-PDI-C60). Their chemical structures were thoroughly characterized by NMR, IR and MALDI-TOF MS spectrometry. In order to gain insights on the structure-property relationship, their self-assembly in gas phase, in solution, and in solid state were characterized using traveling wave ion mobility mass spectrometry (TWIM-MS), UV/Vis absorption, fluorescence emission spectrophotometer, and transmission electron microscopy, respectively. It was found that BPOSS-PDI-OH formed more complicated dimers than BPOSS-PDI-C60. Both samples showed unique aggregation behaviors in solution with increasing concentration, which could be attributed neither to H- nor to J-type and might be related to the discrete dimers. While BPOSS-PDI-C60 could hardly crystalize into ordered structures, BPOSS-PDI-OH could form nanobelt-shaped single crystals, which may hold potential applications in microelectronics.
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