Abstract
Summary Perylene bisimides (PBIs) are one example of useful π-conjugated molecules that can be used in optoelectronic devices as n-type materials with strong visible light absorption. PBIs can self-assemble into a range of structures, but it is rare to be able to control the packing such that the same PBI can form either H-type or J-type aggregates. This is important because the conductivity pathways and optoelectronic properties are directly affected by this packing. Here, we show that we can control the packing of a single PBI functionalized with an amino acid by a subtle change in pH. Under one set of conditions, H-type aggregates form a gel when the pH is decreased. At a slightly different set of starting conditions, J-type aggregates are formed, but they cannot form a gel when the pH is lowered. We show that films formed from the self-assembled structures have very different photoconductive properties.
Highlights
Self-assembly of aromatic organic molecules can be used to prepare materials for a range of optoelectronic and light-driven applications.[1,2,3,4] There are many potential advantages here, including the relatively low cost of the molecules and the potential to fine-tune the properties of the materials by subtle variations in molecular structure and assembly method
We have found that different types of aggregate can be formed from this Perylene bisimides (PBIs) depending on the pH of the solution
A range of PBIs that are functionalized at the imide position with an amino acid have been prepared.[24,25,26,27,28,29,30,31,32]
Summary
Self-assembly of aromatic organic molecules can be used to prepare materials for a range of optoelectronic and light-driven applications.[1,2,3,4] There are many potential advantages here, including the relatively low cost of the molecules and the potential to fine-tune the properties of the materials by subtle variations in molecular structure and assembly method. We have found that different types of aggregate can be formed from this PBI depending on the pH of the solution (and the degree of deprotonation, A1 and A2; Figure 1A).
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