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. 2025 May 27;18(11):2520.
doi: 10.3390/ma18112520.

Synthesis and Photochromic Properties of Diarylethene Derivatives with Aggregation-Induced Emission (AIE) Behavior

Jiaxin Guo  1 , Haoyuan Yu  2 , Yuhua Jin  3
Affiliations

Synthesis and Photochromic Properties of Diarylethene Derivatives with Aggregation-Induced Emission (AIE) Behavior

Jiaxin Guo et al. Materials (Basel). .

Abstract

Photochromic materials have attracted widespread attention due to their potential applications in optical information storage, optoelectronic devices, and fluorescence probes. As a typical photochromic system, diarylethene derivatives are considered one of the most promising photochromic materials due to their outstanding photostability and significant bistable properties. Based on an aggregation-induced emission (AIE) mechanism, this study employed a molecular structural engineering strategy to design and synthesize a series of diarylethene derivatives containing ethyl benzoate substituents. A systematic investigation of the structure-activity relationship between their photochromic behavior and AIE characteristics revealed a dual-state light response mechanism in the solid and solution states. This study demonstrates that the target compounds exhibited significant photochromic responses under UV-visible light irradiation, with enhanced emission in the solid state compared to the solution state, confirming the remarkable enhancement effect of AIE on aggregation. Structural characterization techniques such as nuclear magnetic resonance spectroscopy (NMR) and high-resolution mass spectrometry (H RMS) were employed to elucidate the correlation between molecular conformation and photophysical properties. Furthermore, these materials demonstrated potential for multi-level anti-counterfeiting, high-density optical storage, and bioimaging applications, providing experimental foundations for the development of novel multifunctional photochromic materials.

Keywords: aggregation-induced emission effect; diarylethene derivatives; photophysical properties; photoresponsivity properties.

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Conflict of interest statement

Author Haoyuan Yu was employed by the company Shanghai StarryInk Biotechnology Co., Ltd. The remaining authors declare that the research was conducted in the absence of any commercial or financial relationships that could be construed as a potential conflict of interest.

Figures

Figure 1
Figure 1
Synthesis route of diarylethene boronic ester.
Figure 2
Figure 2
Synthesis route of diarylethene ethyl benzoate.
Figure 3
Figure 3
Synthesis of diarylethene boronic ester.
Figure 4
Figure 4
Synthesis of diarylethene ethyl benzoate.
Figure 5
Figure 5
Color changes in diarylethene benzoate powder under UV/visible light.
Figure 6
Figure 6
UV-Vis absorption spectrum showing changes in diarylethene benzoate in THF (2.0 × 10−5 M) under alternating UV/visible light irradiation.
Figure 7
Figure 7
Absorbance changes in diarylethene benzoate solution under alternating UV/visible light.
Figure 8
Figure 8
Changes in fluorescence emission intensity of solid diarylethene benzoate powder.
Figure 9
Figure 9
Changes in fluorescence emission intensity of diarylethene benzoate in THF solution (5.0 × 10−5 M).
Figure 10
Figure 10
Changes in fluorescence emission intensity of diarylethene benzoate under alternating UV/visible light.
See this image and copyright information in PMC

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