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spiropyran
Soft Matter · 2023 ·Vol. 19 ·期 40 ·7775-7780 · IF 3.4

A spiropyran-based polymer with a stimulus response to water temperature and water content

Xin Li,Yuebo Jin,Ying Li,Hongyan Miao,Haijun Wang,Gang Shi

Temperature-responsive spiropyran-functionalized polymers usually require a thermo-sensitive polymer. However, their temperature response range is limited by the lower critical solution temperature (LCST) of the thermo-sensitive polymer, which does not exceed 37 °C. In this work, a hydrophilic polymer (PHEA-SP) sheet was prepared by photo-initiated copolymerization of hydroxyethyl acrylate (HEA) and a spiropyran crosslinking agent (SP). In water, swelling and hydrogen bonding can increase the ring-opening isomerization probability of spiropyran at the PHEA-SP crosslinking point, thus amplifying the discoloration of spiropyran induced by temperature change. PHEA-SP is very responsive to water temperature in the range of 25–55 °C, due to the amplification of spiropyranoid discoloration described above. This method avoids the dependence of the temperature responsive spiropyran-functionalized polymer on a thermo-sensitive polymer and additional UV light, while increasing the upper limit of the water temperature response to 55 °C. In addition, PHEA-SP also shows responsivity to water content in ethanol solution from 0.3% to 100%.

研究领域: 材料科学 · 化学
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ACS Applied Nano Materials · 2023 · IF 5.9

Photoresponsive Electrospun Nanowire Films Based on N-Isopropylacrylamide and Spiropyran for Regulating Microenvironmental Humidity

Na Huang,Ning Zhao,Ce Zhang,Chunhao Li,Xia Wei,Yang Zhang,Yongsheng Bao,Shuai Wang

Based on the goal to improve the humidity index of the microenvironment and enhancing human comfort, this study used electrospinning to prepare several photoresponsive films with reversible regulation of wettability and microenvironmental humidity from copolymers of acrylated spiropyran (SPA), N-isopropylacrylamide (NIPAm), and methyl methacrylate (MMA). According to the photoisomerization mechanism of spiropyran, the simple ultraviolet (UV)–visible light (vis) reversible light radiation change makes the spiropyran unit switch between the polar ring-opened form and the nonpolar ring-closed form. Utilizing this transition can easily regulate the wettability of the film surface and microenvironmental humidity. The experimental results show that poly(SPA1-co-NIPAm2-co-MMA8) nanowire film has the best ability to regulate wettability and humidity; the wettability can vary within a range of 13° and the microenvironmental humidity up to 7.2%.

研究领域: 材料科学 · 化学 · 环境科学
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PHYSICAL CHEMISTRY CHEMICAL PHYSICS · 2026 · IF 3

Thermodynamic Selectivity and Kinetic Control in the Encapsulation of Spiropyran Derivatives by Cucurbit[8]uril

Yinghui Niu,Fengbiao Chen,Xinru Guo,Yinjun Chen,Jin Wen,Meifang Zhu

Spiropyrans (SPs) are promising building blocks for stimuli-responsive delivery because of their sensitivity to pH, light, and heat. However, their intrinsic hydrophobicity and limited stability in aqueous media severely restrict practical use under physiological conditions. Here, to overcome this aqueous-compatibility bottleneck, we propose a host-guest-guided design and screening strategy that integrates thermodynamic binding analysis with kinetic assessment, followed by experimental validation, to identify effective supramolecular complexes for controlled loading/release in water. Using cucurbit[8]uril (CB[8]) and three spiropyran derivatives (SP1–3) with their merocyanine isomers (MC1–3) as a model system, we first quantify host-guest recognition from a thermodynamic perspective by density functional theory. We then resolve stimulus-coupled loading/release kinetics by explicit-solvent umbrella sampling, yielding potential of mean force profiles that reveal a pronounced size-dependent kinetic-gating mechanism: MC1–2 display an entry–retention behavior consistent with efficient loading and high kinetic retention, while the bulkier SP3/MC3 is sterically restricted and favors a shallow capping mode with limited encapsulation and faster escape. ¹H NMR and time-resolved UV-Vis measurements further verify the strong host-guest interactions and the host-modulated isomerization kinetics, in close agreement with the differentiated confinement regimes predicted by simulation. Beyond CB[8], comparative simulations indicate that γ-cyclodextrin provides a more accommodating cavity environment for SP2. Overall, this work demonstrates a generalizable theory-to-experiment workflow that couples thermodynamic and kinetic criteria to rationally select host-guest pairs, offering a transferable framework for designing low-leakage, multi-stimuli-responsive supramolecular delivery and controlled-release platforms.

✓ 已验证 DOI PubMed 高影响因子
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FOOD CHEMISTRY · 2024 · IF 8.5

β-cyclodextrin/spiropyran-functionalized optical-driven hydrogel film for bisphenol A detection in food packaging

Jie Liu,Jiang Zhou,Qiang Xi,Shengyuan Yang,Wenfang Du,Fubing Xiao

Bisphenol A (BPA), an endocrine disruptor , is widely used in food packaging materials , including drink containers. Sensitive detection of BPA is crucial to food safety. Herein, we have developed a novel optical-driven hydrogel film sensor for sensitive BPA detection based on the displacement of spiropyran (SP) from β -cyclodextrin ( β -CD) cavity by BPA followed by the photochromism of the released SP. The released SP converts to the ring-opened merocyanine form which shows an enhanced red fluorescence in the dark. The sensor demonstrates a linear detection range from 0.1 to 20 μg mL −1 with a limit of detection at 0.027 μg mL −1 and a limit of quantification at 0.089 μg mL −1 . Notably, the proposed β -CD/SP hydrogel can be reused due to the reversible isomerization of SP and the reversible host–guest interaction. This sensor also shows good performance for BPA determination in real samples, indicating its great potential for food safety monitoring.

研究领域: 分析化学 · 食品科学 · 环境科学
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POLYMER · 2025 · IF 4.5

Preparation, performance and application of photochromic thermal expansion microcapsules containing spiropyran in water-based ink

Jingjing Ren,Li An,Siqiao Zhang,Ran Mo,Fanghua Pan,Yuwei Hao,Zhiqing Xin,Zhicheng Sun

A novel type of photochromic thermally expandable microcapsules (PTEMs) were prepared through suspension polymerization. The shell material of the microcapsules consisted of acrylonitrile (AN), methyl methacrylate (MMA), and methyl acrylate (MA). The core material utilized n-hexane as a foaming agent containing photochromic dye (spiropyran). On the basis of the preparation, the investigation further focused on the chemical structure, surface morphology, particle size, color-changing ability, and thermal expansion of the microcapsules. Additionally, the PTEMs were used in water-based inks with good compatibility and for screen printing to obtain patterns. Meanwhile, the color changeability of the printed samples was evaluated using a portable colorimeter. Eventually, the results demonstrated that the printed products exhibited excellent color change and thermal expansion capabilities. In future, the PTEMs will have the potential to develop water-based ink applications in anti-counterfeiting and smart packaging.

研究领域: 材料科学 · 化学工程 · 印刷技术
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DESIGNED MONOMERS AND POLYMERS · 2016 · IF 1.497

Self-assembly and morphology transition of amphipathic spiropyran-based random copolymers to control drug release

Si Chen,Hui Liu,Jin Hu,Hu Zou,Yang He

An amphipathic spiropyran-based random copolymer P(SPMA-co-DMAEMA) was synthesized by atom transfer radical polymerization, and the resulting copolymer was characterized by means of 1H nuclear magnetic resonance spectroscopy, Fourier transform infrared spectroscopy, and gel permeation chromatography. The self-assembly behaviors and morphology transition were systematically investigated under single and combined external environmental stimuli by transmission electron microscopy. With coumarin 102 as the model drug molecule, the self-assembly micelles were used to control drug loading, release, and re-encapsulation to some extent. The characterization results indicated the successful preparation of the spiropyran-based random copolymer P(SPMA-co-DMAEMA). The external stimuli had some influences on the morphology of the self-assembly aggregate, and the ‘schizophrenic’ behavior was interestingly found in this work. The drug release experiments showed the reversible loading and release process up to a point, which might expand the potential application domain of the amphiphilic spiropyran-based random copolymer in drug delivery.

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JOURNAL OF MATERIALS CHEMISTRY · 2012 ·Vol. 22 ·期 48 ·25019-25026 · IF 5.968

Microwave-assisted crystallization inclusion of spiropyran molecules in indium trimesate films with antidromic reversible photochromism

Feng Zhang,Xiaoqin Zou,Wei Feng,Xiaojun Zhao,Xiaofei Jing,Fuxing Sun,Hao Ren,Guangshan Zhu

An indium trimesate metal–organic framework (JUC-120) which possesses a cubic zeolitic MTN topology, as a new analogue to MIL-100(Al, Fe or Cr) compounds, has been successfully synthesized. Its structure exhibits a mesoporous cage (26 Å) and high thermal stability. The assembly of nitrobenzospiropyran derivatives (BSP) into JUC-120 nanocrystals (BSP/JUC-120) is achieved by a microwave-assisted crystallization inclusion approach. The BSP/JUC-120 films have been prepared on quartz wafers by a spin-coating method. The successful encapsulation of BSP molecules into the mesopores of the JUC-120 structure has been verified by N2 adsorption and TGA measurements. The photochromic properties of BSP/JUC-120 films are studied by the UV-Vis and fluorescence spectroscopies. More interestingly, metastable open merocyanine (OMC) species are directly generated from the closed spiropyran form (CSP) without photoirradiation and stabilized for a long period in the BSP/JUC-120 film. The open merocyanine isomer bleaches to the closed spiropyran form by ultraviolet or visible light, and the coloration is regained upon standing in the dark, exhibiting antidromic photochromism. Moreover, the BSP/JUC-120 film shows high reversibility and thermal stability of photochromism. This highly efficient MOF film is expected to be promising in the applications of optical devices.

研究领域: 材料科学 · 光化学 · 纳米技术 · 金属有机框架(MOFs) · 光学器件
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DYES AND PIGMENTS · 2014 · IF 3.468

Synthesis of amphiphilic spiropyran-based random copolymer by atom transfer radical polymerization for Co2+ recognition

Huanqing Cui,Hui Liu,Si Chen,Ruimeng Wang

An amphiphilic spiropyran-based random copolymer containing methacrylic acid unit has been prepared and investigated with obvious negative solvatochromism in five different solvents. It was found that the polarity of comonomer influenced the photochromic behavior of spiropyran. The synthesized copolymer exhibited a good reversible behavior in aqueous solution: the addition of strong acid promoted the isomerization from spiropyran (SP) to merocyanine (MC), and the inverse process was achieved by the introduction of strong base. Much more importance, the effect of comonomer was utilized for the selective Co 2+ recognition. The locations of the maximum absorption peak stay almost as same as MC when it is complexed with Cu 2+ , Mn 2+ and Hg 2+ . The location, however, moves from 551 nm to 526 nm upon complexation with Co 2+ . The obvious color change of the solution from purple to claret-red after complexation with Co 2+ was observed. This interesting phenomenon is practically convenient for the visual recognition of Co 2+ .

研究领域: 高分子化学 · 传感器与检测 · 光响应材料 · 配位化学
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Laser & Photonics Reviews · 2024 ·Vol. 18 ·期 12 ·2400812 · IF 9.8

Dynamic Information Encryption and Coding using Liquid Crystal Soft Helical Microstructures with Spiropyran Photochromic Switch

Guangyin Qu,Xiaojuan Zhang,Siqi Li,Yan Kuai,Feng Xu,Liang Lu,Yu Liu,Zhigang Cao,Benli Yu,Anderson S. L. Gomes,Zhijia Hu

In contrast to conventional anti-counterfeiting technologies, which are susceptible to decryption and exhibit limited effectiveness, the utilization of light to dynamically configure soft materials in a fully reversible and programmable manner not only enhances data security but also improves anti-counterfeiting performance. However, achieving precise control over reflection structural colors and laser wavelengths within a broad dynamic range remains a challenge. In this study, a UV-responsive soft helical superstructure is established by combining a photochromic compound with chiral liquid crystals (LCs). By manipulating the Bragg reflection angle, structural reflection colors ranging from red to cyan are successfully achieved. The introduction of an anti-counterfeiting technique that embeds diverse micro-structures provides features such as color adjustability, erasability, and angle-dependent stability. Using the unique properties of this soft helical superstructure, the implementation of a wavelength-tunable LC bandgap laser through optically reconfigurable Förster resonance energy transfer processes is showcased. Furthermore, a straightforward prototype information encoder is developed to mimic the processes of information encoding and decoding, bypassing the need for complex algorithm design. This research underscores the practicality of LC helical soft systems, emphasizing their distinctive responsiveness to light and their applicability in optical programming photonics.

研究领域: 光学材料 · 软物质物理 · 光子学 · 信息安全 · 功能材料 · 分子光化学
✓ 已验证 DOI 高影响因子
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Gels · 2022 ·Vol. 8 ·期 4 ·208 · IF 4.432

Tough, Self-Recoverable, Spiropyran (SP3) Bearing Polymer Beads Incorporated PAM Hydrogels with Sole Mechanochromic Behavior

Jianxiong Xu,Yuecong Luo,Yin Chen,Ziyu Guo,Yutong Zhang,Shaowen Xie,Na Li,Lijian Xu

Spiropyran-containing hydrogels that can respond to external stimuli such as temperature, light, and stress have attracted extensive attention in recent years. However, most of them are generally dual or multiple stimuli-responsive to external stimuli, and the interplay of different stimulus responses is harmful to their sensitivity. Herein, spiropyran bearing polymer beads incorporated PAM (poly(AM–co–MA/DMSP3)) hydrogels with sole mechanochromic properties were synthesized by emulsion polymerization of acrylamide (AM) and methyl acrylate (MA) in the presence of spiropyran dimethacrylate mechanophore (DMSP3) crosslinker. Due to the hydrophobic nature of MA and DMSP3, the resultant hydrogel afforded a rosary structure with DMSP3 bearing polymer beads incorporated in the PAM network. It is found that the chemical component (e.g., AM, MA, and DMSP3 concentrations) significantly affect the mechanical and mechanoresponsive properties of the as-obtained poly(AM–co–MA/DMSP3) hydrogel. Under optimal conditions, poly(AM–co–MA/DMSP3) hydrogel displayed high mechanical properties (tensile stress of 1.91 MPa, a tensile strain of 815%, an elastic modulus of 0.67 MPa, and tearing energy of 3920 J/m2), and a good self-recovery feature. Owing to the mechanoresponsive of SP3, the hydrogels exhibited reversible color changes under force-induced deformation and relaxed recovery states. More impressive, the poly(AM–co–MA/DMSP3) hydrogel showed a linear correlation between tensile strain and chromaticity (x, y) as well as a stain and resting time-dependent color recovery rate. This kind of hydrogel is believed to have great potential in the application of outdoor strain sensors.Keywords:mechanophore;mechanoresponsive hydrogels;emulsion polymerization;spiropyran

研究领域: 材料科学 · 高分子化学 · 力学
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JOURNAL OF APPLIED POLYMER SCIENCE · 2025 · IF 2.8

Triple Stimuli Responsive p(NIPAM-co-MAA-co-SPMA) Hydrogel for Controlled Anticancer Drug Delivery: Synthesis, Characterization, and Performance Evaluation

Yuanpeng Cai,Danyang Li,Yufei Ling,Huihui Jiang,Hui Liu

A novel triple-responsive composite hydrogel, p(NIPAM-co-MAA-co-SPMA), was designed and synthesized via free radical polymerization, incorporating N-isopropylacrylamide (NIPAM) for temperature responsiveness, methacrylic acid (MAA) for pH sensitivity, and spiropyran methacrylate (SPMA) for light responsiveness. This study aimed to develop a novel stimuli-responsive sustained release drug delivery system. The composition and structure of the hydrogel were characterized by nuclear magnetic resonance spectroscopy (NMR), Fourier transform infrared spectroscopy (FTIR), X-ray photoelectron spectroscopy (XPS), and scanning electron microscopy (SEM). Doxorubicin (DOX) was used as a model drug to evaluate loading and release behavior. The hydrogel achieved a drug loading content (DLC) of 25.7% and a drug loading efficiency (DLE) of 74.3% and enabled controlled release with approximately 89% cumulative DOX release within 6 h under combined thermal, acidic, and ultra-violet light stimuli. Cytotoxicity assays and cellular uptake studies confirmed the excellent biocompatibility of the hydrogel and its efficacy in suppressing cancer cell growth. These results highlight the potential of p(NIPAM-co-MAA-co-SPMA) as an intelligent platform for on-demand targeted anticancer therapy.

研究领域: 高分子材料科学 · 肿瘤学 · 药物递送系统 · 生物医学工程 · 智能药物释放 · 纳米医学
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ACS Applied Polymer Materials · 2026 · IF 5.2

Dynamic Responsive Poly(methyl Methacrylate)-Spiropyran Microspheres via Membrane Emulsification for Advanced Solid-State Photochromic Anticounterfeiting

Le Li,Xia Bao,Yujie Sun,Chen Liu,Li Li,Lulu Bu,Chao Gao,Xian Liang,Peng Xi,Quan Li

Photochromic materials have garnered significant attention for applications in anticounterfeiting and information encryption. However, their practical utilization in solid states remains challenging due to restricted molecular isomerization. In this work, we successfully synthesized PMMA-SP microspheres via a membrane emulsification-solvent evaporation approach, which enables efficient and reversible solid-state photochromism. Under UV irradiation, the microspheres undergo a rapid color transition from pale pink to deep purple, accompanied by enhanced fluorescence emission, and revert to their original state upon exposure to visible light. Furthermore, flexible PVA/PMMA-SP composite films were fabricated, allowing reversible and high-contrast photopatterning through the photomasks. Notably, these films exhibit distinct color changes, even under natural sunlight, providing a straightforward authentication feature. Collectively, this study offers a facile and scalable strategy for designing rewritable photochromic materials with considerable potential for advanced optical security applications.

CAS / MDL: 9002-89-5 68-12-2
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