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. 2018 Mar 15;24(16):4006-4010.
doi: 10.1002/chem.201800201. Epub 2018 Feb 19.

Controlling Photoconductivity in PBI Films by Supramolecular Assembly

Emily R Draper  1 , Lewis J Archibald  1 , Michael C Nolan  1   2 , Ralf Schweins  3 , Martijn A Zwijnenburg  4 , Stephen Sproules  1 , Dave J Adams  1
Affiliations

Controlling Photoconductivity in PBI Films by Supramolecular Assembly

Emily R Draper et al. Chemistry. .

Abstract

Perylene bisimides (PBIs) self-assemble in solution. The solubility of the PBIs is commonly changed through the choice of substituents at the imide positions. It is generally assumed this substitution does not affect the electronic properties of the PBI, and that the properties of the self-assembled aggregate are essentially that of the isolated molecule. However, substituents do affect the self-assembly, resulting in potentially different packing in the formed aggregates. Here, we show that the photoconductivity of films formed from a library of substituted PBIs varies strongly with the substituent and demonstrate that this is due to the different ways in which they pack. Our results open the possibility for tuning the optoelectronic properties of self-assembled PBIs by controlling the aggregate structure through careful choice of substituent, as demonstrated by us here optimising the photoconductivity of PBI films in this way.

Keywords: aggregation; perylene; perylene bisimide; photoconductivity; self-assembly.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
(Top) Photograph of PBIs in solution. (Bottom) Structures of the PBIs; the letter represents the amino acid used for functionalisation.
Figure 2
Figure 2
(a) UV/Vis absorption spectra of PBI‐A and (b) PBI‐F showing differences in aggregation. (c) Grow in of EPR signal in the PBI‐A solution after irradiation with 365 nm; spectra recorded at 2 min intervals over 33 min. (d) overlay of the normalized EPR spectra corresponding to maximum radical content for each PBI.
Figure 3
Figure 3
(a) Bar chart showing the photoresponse of the films at 4 V to 365 nm. The absolute values are tabulated in the Supporting Information, Table S13. (b–d) UV/Vis absorption spectra of dried solutions before irradiation (solid line) and after irradiation for 10 minutes with 365 nm LED (red line) for (b) PBI‐A (c) PBI‐H and (d) PBI‐F.
Figure 4
Figure 4
Grow in of EPR signal with time after irradiation with 365 nm light for the films of the different PBIs.
See this image and copyright information in PMC

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