Self-assembly, optical and electrical properties of perylene diimide dyes bearing unsymmetrical substituents at bay position

Scientific Reports
Fengxia ZhangJingmin Shi

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 ma...Continue Reading

References

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Citations

Sep 19, 2019·Chemistry : a European Journal·Adela I CarrilloAnabel E Lanterna
Jan 27, 2019·Dalton Transactions : an International Journal of Inorganic Chemistry·Pagidi SudhakarPakkirisamy Thilagar
Dec 8, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Stefania AivaliJoannis K Kallitsis
Oct 3, 2020·The Journal of Chemical Physics·Sai Vamsi Krishna IsukapalliSivaranjana Reddy Vennapusa
May 1, 2020·The Journal of Physical Chemistry Letters·Yong-Jae KimHwan-Jin Jeon
Jul 24, 2020·The Journal of Organic Chemistry·Tankut Türel, Suresh Valiyaveettil
Dec 10, 2019·ACS Omega·Francesco Muniz-MirandaAndrea Pucci
Sep 9, 2021·Nanoscale·Qiaochu JiangXianbao Sun
Jan 28, 2022·The Journal of Physical Chemistry. a·Hassiel Negrin-YuveroSebastian Fernandez-Alberti

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Methods Mentioned

BETA
nuclear
infrared spectroscopy
silica gel column chromatography

Software Mentioned

Gaussian03

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