Issue 31, 2020

Self-assembly of an alkynylpyrene derivative for multi-responsive fluorescence behavior and photoswitching performance

Abstract

Highly emissive fluorophores based on polyaromatic hydrocarbons with tunable emission properties and aggregated structures play a very important role in relevant functional studies. In this study, a novel alkynylpyrene derivative 1 was synthesized, which exhibits unimolecular to excimer emission in methanol with an increasing concentration accompanied by the formation of nanovesicles via the π–π stacking, hydrogen bond and hydrophobic interaction. The self-assembly behavior as well as emission properties of 1 in aprotic polar solvents (ACN, acetone, DMF and DMSO) can also be adjusted by the volume fraction of the poor solvent H2O, which can induce 1 self-assembly to excimer state and could be applied in information transfer. Moreover, upon visible light irradiation, photoswitchable performance of nanovesicles of 1 was observed in which the emission markedly changes from yellow to blue; this is attributed to the cycloaddition reaction of alkynyl groups and singlet oxygen, which can be generated without the addition of external photosensitizers. The multi-responsive and fluorescence behavior of the alkynylpyrene derivative show that the self-assembly can be used to expand the development of this type of fluorophores, and the novel photoinduced tunability of the fluorescence emission provides an effective strategy to obtain high-performance transmitting and sensing materials.

Graphical abstract: Self-assembly of an alkynylpyrene derivative for multi-responsive fluorescence behavior and photoswitching performance

Supplementary files

Article information

Article type
Paper
Submitted
23 Jun 2020
Accepted
06 Jul 2020
First published
06 Jul 2020

Soft Matter, 2020,16, 7390-7399

Self-assembly of an alkynylpyrene derivative for multi-responsive fluorescence behavior and photoswitching performance

C. Xia, N. Wang, P. Sun, S. Tang, X. Xu, Y. Tan and X. Xin, Soft Matter, 2020, 16, 7390 DOI: 10.1039/D0SM01148G

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