Perylene Diimide Dyes Aggregates: Optical Properties and Packing Behavior in Solution and Solid State

Ma, Yongshan; Wang, Chen-Hui; Zhao, Yingjie; Yu, Ying; Han, Chao; Qiu, Xin-Jian; Shi, Zhiqiang

doi:10.1080/10610270600902324

Cited by 52 publications

(23 citation statements)

References 27 publications

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“…1b ). The spectra of 1 show two absorption bands (528 nm, 496 nm) and a broad shoulder peak around 460 nm, which are in accord with the characteristics of the 0–0, 0–1, and 0–2 transition energy 29 . Also, these spectra conform to the absorption peaks of 2 appeared at 527 nm, 493 nm, and a shoulder around 461 nm.…”

Section: Resultssupporting

confidence: 74%

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

Zhang

Chi

et al. 2018

Sci Rep

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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.

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Section: Resultssupporting

confidence: 74%

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

Zhang

Chi

et al. 2018

Sci Rep

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“…As free monomers, the normal progression of Franck–Condon factors is A 0–0 > A 0–1 . However, the 0–1 transition increased as the monomer began to aggregate . From 10 −5 to 10 −4 M, the 0–1 transition absorptions of PDCDA showed scarcely any increase in aqueous solution, suggesting that the π–π interactions do not occur at higher concentrations.…”

Section: Resultsmentioning

confidence: 96%

A water‐soluble fluorescent pH probe based on perylene dyes and its application to cell imaging

Zhang

et al. 2015

Luminescence

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A fluorescent pH probe, N,N'-bi( l-phenylalanine amine)-perylene-3,4;9,10-dicarboxylic diimide (PDCDA) was synthesized and used for pH sensing in living cells. A significant fluorescence intensity change was observed over a pH range from 7.0 to 4.0. Electrostatic potential maps (MEP) suggested that the electronic repulsion between PDCDAs was increased by the high negative electrostatic potential which resulted in a high water solubility of PDCDA. PDCDA was successfully applied as a high-performance fluorochrome for living HeLa cell imaging. The results demonstrate that the probe PDCDA is a good candidate for monitoring pH fluctuations in living cells with good water solubility, low cytotoxicity, high fluorescence quantum yield and photostability.

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“…They were purified through conventional procedures prior to use. N, N 0 -dicyclohexyl-3,4,9,10-tetracarboxylic acid bisimide 1 and N, N 0 -dicyclohexyl-1-nitroperylene-3,4,9,10-tetracarboxylic acid bisimide 2 were synthesized according to the literature procedure [19,20] …”

Section: Methodsmentioning

confidence: 99%

Self-assembly, optical and electrical properties of five membered O- or S-heterocyclic annulated perylene diimides

Shi

Zhang

et al. 2016

Dyes and Pigments

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Perylene Diimide Dyes Aggregates: Optical Properties and Packing Behavior in Solution and Solid State

Cited by 52 publications

References 27 publications

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

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

A water‐soluble fluorescent pH probe based on perylene dyes and its application to cell imaging

Self-assembly, optical and electrical properties of five membered O- or S-heterocyclic annulated perylene diimides

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