Abstract
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.
Highlights
Echoing the Material Genome Initiative [1], the study of shape amphiphiles has brought us a new way to understanding structure-property relationships in materials science by combiningMolecules 2019, 24, 2114; doi:10.3390/molecules24112114 www.mdpi.com/journal/moleculesMolecules 2019, 24, 2114 molecular moieties of different shapes and functions and letting anisotropy promote their hierarchical self-assembly [2,3,4]
As shown in Scheme 1, based on isobutyl-functionalized polyhedral oligomeric silsesquioxane (BPOSS)-perylene tetracarboxylic diimide (PDI)-OH was synthesized via a one-pot condensation method where the two amines were competing to react with the dianhydride to form the diadducts [56]
BPOSS-PDI-OH were obtained in an acceptable yield of ~30%
Summary
Echoing the Material Genome Initiative [1], the study of shape amphiphiles has brought us a new way to understanding structure-property relationships in materials science by combining. Is an organic shape-persistent molecule with spherical skeleton possessing unique π–π interactions and intriguing electronic properties [12,13,14,15,16,17] Using these molecular nanoparticles, one can build shape amphiphiles with uniform molecular size and precise molecular structures [18]. The interplay between different motifs might lead to ordered arrangement of PDI and C60 to take advantage of their useful electronic properties [51] In this case, we anticipate that the assembly of the triblock shape amphiphile could help control the molecular packing and crystal morphology of the assemblies, which is critical to their applications in nanostructure engineering [52,53]. These model compounds were thoroughly characterized in terms of their assembly in gas phase, in solution, and in condensed state
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