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Tetraphenylethenyl-modified perylene bisimide: aggregation-induced red emission, electrochemical properties and ordered microstructures

Zhao, Qiuli, Zhang, Shuang, Liu, Yi, Mei, Ju, Chen, Sijie, Lu, Ping, Qin, Anjun, Ma, Yuguang, Sun, Jing Zhi, Tang, Ben Zhong·2012·Journal of Materials Chemistry

Abstract

Perylene bisimides (PBIs) are one class of the most explored organic fluorescent materials due to their high fluorescence quantum efficiency, electron transport behaviour, and ready to form well-tailored supramolecular structures. However, they suffer from heavy aggregation-caused quenching (ACQ) effect which has greatly limited their potential applications. We successfully tackle this problem by chemical modification of the PBI core with two tetraphenylethene (TPE) moieties at the bay positions. This modification resulted in a pronounced fluorescence red-shift (over 120 nm) and rendered the derivatives (1,6-/1,7-DTPEPBI) with evident aggregation-induced emission (AIE) behaviour. Both 1,6-DTPEPBI and 1,7-DTPEPBI emit bright red fluorescence in the solid state. The fluorescence quantum efficiency of the aggregates of 1,7-DTPEPBI (ΦF, solid = 29.7%, formed in a hexane/dichloromethane mixture, fh = 90%) is about 424 times higher than that in dichloromethane solution (ΦF, solut = 0.07%). Electrochemical investigation results indicated that 1,7-DTPEPBI sustained the intrinsic n-type semiconductivity of PBI moiety. In addition, morphological inspection demonstrated that 1,7-DTPEPBI molecules easily form well-organized microstructures despite the linkage of the PBI core with bulky TPE moieties.

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Metadata

Authors
Zhao, Q., Zhang, S., Liu, Y., Mei, J., Chen, S., Lu, P., Qin, A., Ma, Y., Sun, J. Z., & Tang, B. Z.
Venue
Journal of Materials Chemistry
Published
2012
Volume
22
Issue
15
Pages
7387
ISSN
  • 0959-9428 (ISSN-L)
  • 1364-5501
OpenAlex
W2037731960
Cited by
168
References
2
FWCI
7.67
Type
journal article
Language
en
Open access
closed

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CoChat. (2026). Citation check: Tetraphenylethenyl-modified perylene bisimide: aggregation-induced red emission, electrochemical properties and ordered microstructures. https://app.cochat.ai/papers/10.1039/c2jm16613e
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Zhao, Q., Zhang, S., Liu, Y., Mei, J., Chen, S., Lu, P., Qin, A., Ma, Y., Sun, J. Z., & Tang, B. Z. (2012). Tetraphenylethenyl-modified perylene bisimide: aggregation-induced red emission, electrochemical properties and ordered microstructures. Journal of Materials Chemistry. https://doi.org/10.1039/c2jm16613e

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