Abstract
Perylene diimides (PDIs) are one class of the most explored organic fluorescent materials due to their high luminescence efficiency, optoelectronic properties, and ready to form well-tailored supramolecular structures. However, heavy aggregation caused quenching (ACQ) effect in solid state has greatly limited their potential applications. We have easily solved this problem by chemical modification of the PDI core with only phenoxy moietie at one of the bay position. In this paper, we report two perylene bisimides with small rigid substituents, 1- phenol -N, N’-dicyclohexyl perylene-3,4,9,10-tetracarboxylic diimide (PDI 1) and 1- p-chlorophenol-N, N’-dicyclohexyl perylene-3,4,9,10-tetracarboxylic diimide (PDI 2) possess both well defined organic nanostructures and high fluorescence quantum yield in the solid state. In contrast, 1-propanol-N, N’-dicyclohexyl perylene-3,4,9,10-tetracarboxylic diimide (PDI 3) bearing a straight chain only shown weak orange fluorescence. In addition, morphological inspection demonstrated that PDI 3 molecules easily form well-organized microstructures despite the linkage of the PDI core with a straight chain. The present strategy could provide a generic route towards novel and advanced fluorescent materials and these materials may find various applications in high-tech fields.
Highlights
Perylene diimides (PDIs) are one kind of the most investigated organic dyes because of their excellent chemical, thermal, and optical stabilities, as well as their high luminescence efficiency and novel optoelectronic properties[1,2,3,4,5]
Substitution at the imide position can not affect the properties and electronic structures of PDIs, because the nodes in both lowest unoccupied molecular orbital (LUMO) and highest occupied molecular orbital (HOMO) levels limit the electronic interactions between PDI and corresponding substituents[24]
The aggregations of the molecules are dominated by the PDI rings and the substituent segments
Summary
The fluorescence spectra of PDIs 1, 2, and 3 in DCM depict the same structure with approximate mirror images of the absorption spectrum, and the emission peaks are appeared at 560 nm, 557 nm, and 568 nm for 1, 2, and 3, with corresponding Stokes shifts of 32 nm, 30 nm, and 16 nm, respectively This indicated that the Stokes shift decreased along with the introduction of chlorinatomin or phenoxy to the electron rich ether substituent. The intensity of diffraction peak at 25.6° (3.4 Å) (which can be attributed to the π-π stacking distance of PDI rings between the adjacent molecules) decreases obviously This result suggests that the π-π stacking interactions of 3 units are weak. Compound 3 could be a candidate material for acquiring well defined organic nanostructures with good charge-transporting
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