Research Progress on Photochromic Spiropyrans in the Solid State

doi:10.6023/cjoc202312017

Abstract

In recent years, organic photochromic materials have drawn continuous interest due to their wide application value in fields such as molecular switches, anti-counterfeiting and biological fluorescence imaging. Spiropyran (SP) compounds have the advantages of simple preparation, easy modification and good optical properties. They can undergo structural and performance changes under various external stimuli such as light, heat, electricity, acid-base, and external forces. Therefore, they can be applied in multiple fields. Solid spiropyran compounds without a matrix are difficult to undergo photochromic reactions due to their tightly packed molecules and lack of spatial free volume. Development of photochromic SP in the solid state is a significant trend in new materials. The research progress on photochromic spiropyrans in the solid state is summarized with the relationship between molecular structures and properties as an emphasis.

Key words: spiropyran, solid state, photochromism

Cite this article

Suhua Yang, Xiaoyin Liu, Lifei Zou, Jie Han. Research Progress on Photochromic Spiropyrans in the Solid State[J]. Chinese Journal of Organic Chemistry, 2024, 44(6): 1719-1732.

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Fig. & Tab. 15

Scheme 1. Photochromic mechanism of spiropyran compounds

Scheme 2. Photochromic mechanism of 1 and 2

Figure 1. Color change of crystal 2 (a) Before irradiation, (b) after UV irradiation at room temperature, and (c) after UV irradiation at 90 K. Reproduced from Ref. [21] by permission of John Wiley & Sons Ltd.

Figure 3. Fluorescent and visible images of 12 (the closed form TPEA-SP and open mwrocyanine form TPEA-MC) powders under the alternating UV and visible light treatment Reproduced from Ref. [31] with permission. Copyright 2021 American Chemical Society.

Figure 5. Photographs of the 19 powder under natural light (A) and 365 nm UV light (B) and photographs of 19 powder after UV irradiation under natural light (C) and 365 nm UV light (D) Reproduced from Ref. [36] by permission of John Wiley & Sons Ltd.

Figure 6. Color change of 20 crystal before and after UV irradiation (top) and color changes of 21a (a) and 21a' (b) before and after UV irradiation (bottom) Reproduced from Ref. [37]. Copyright 2018, with the permission from the Royal Society of Chemistry.

Figure 8. Photographs of photochromic crystals of (a) 42, (b) 48a, (c) 48b, and (d) 48c before (top) and after (bottom) irradiation of 365 nm for 5 min (A)[54] and photographs of the single crystal of 49 ([6'-SP]PF6) before and after UV light irradiation for 5 min (B)[55] Reproduced from Ref. [54] with permission. Copyright 2019 American Chemical Society. Reproduced from Ref. [55] with permission. Copyright 2020 American Chemical Society.

Scheme 3. Schematic synthesis of 54 and 55

Figure 9. (a) Photographs of powders of 58 after 365 nm UV irradiation for different times and (b) evolution of the photogenerated absorption of 58 after 0, 0.166, 0.5, 1, 1.5, 2, 3, 4, 5, 8, 15 and 30 min of UV irradiation (365 nm) Reproduced from Refs. [64] with permission. Copyright 2013 American Chemical Society.

Figure 10. UV-Vis absorption spectra of a thin film of 63 recorded under ultraviolet irradiation (The inset shows digital photographs of SP and MC forms of the cage 63 in the solid state) Reproduced from Refs. [76] with permission. Copyright 2017 American Chemical Society.

Figure 12. Color and fluorescent images of solid compound 67 before and after illumination Reproduced from Ref. [79] by permission of John Wiley & Sons Ltd.

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