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Spiropyran
LUMINESCENCE · 2019 ·Vol. 34 ·期 7 ·707-714 · IF 1.691

Selective sensing Ca2+ with a spiropyran-based fluorometric probe

Li Wang,Yuanjun Yao,Jiao Wang,Chuan Dong,Hui Han

Spiropyran (SP) and its derivatives operate between their ring opening and closing forms as a versatile molecular platform for the fluorescence detection of cations and anions, using a colour change for signalling. A functionalized SP fluorescence probe, L , was prepared and characterized. Probe L can detect Ca 2+ with a fluorescence ‘turn-on’ response in ethanol solution. It selectively binds Ca 2+ to form a 1:1 ligand/metal complex, which produced a new emission band centred at 604 nm. The sensing result was clearly observed by the solution colour change from colourless to pink under visible light, and from blue to red under ultraviolet light. The detection limit was calculated to be 4.53 × 10 −8 M for Ca 2+ . The probe provides another possibility that SP-based derivatives could be used for the development and detection of metal ions in environmental and physiological systems.

研究领域: 分析化学 · 生物化学
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NEW JOURNAL OF CHEMISTRY · 2020 ·Vol. 44 ·期 36 ·15350-15353 · IF 3.288

The photo-/thermo-chromism of spiropyran in alkanes as a temperature abuse indicator in the cold chain of vaccines

Mei Gao,Chaofan Lian,Rang Xing,Jie Wang,Xuefei Wang,Zhiyuan Tian

The optimal storage temperature for vaccines ranges from 2 °C to 8 °C. Electronic thermometers can provide real-time and remote temperature monitoring but are not applicable for individual packages. However, it is known that few alkanes have melting points in this range. The photo-induced conversion of colorless spiropyran to blue merocyanine can be thermally reversed, resulting in decoloration. By dispersing spiropyran in a mixture of n-tetradecane and n-pentadecane with the melting point of 8 °C, an accurate and low-cost thermochromism indicator to record temperature abuse has been designed. The results showed that the thin label based on this system has taken a permanent decoloration within 10 min of the temperature exceeding 8 °C.

研究领域: 生物化学 · 制药工程
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MACROMOLECULAR CHEMISTRY AND PHYSICS · 2013 ·Vol. 214 ·期 6 ·716-725 · IF 2.386

Synthesis of Photoresponsive Spiropyran-Based Hybrid Polymers and Controllable Light-Triggered Self-Assembly Study in Toluene

Li Ma,Jinze Li,Dan Han,Haiping Geng,Guangxin Chen,Qifang Li

A series of polyhedral oligomeric silsesquioxane end-capped poly(spiropyran-containing methacrylate) (POSS–PSPMA) polymers, a kind of photoresponsive hybrid polymer, are synthesized via atom transfer radical polymerization. It is proved that the molecular weight of POSS–PSPMA is sharply increased by raising the proportion of methanol or the concentration of the reactants. The self-assembly behavior of POSS–PSPMA is studied in toluene: under the control of UV and visible light, POSS–PSPMA can reversibly self-assemble into aggregates because the charged merocyanines (MC) form stacks. These MC stacks act as non-covalent crosslinking points and POSS shell guarantees the stability of the aggregates. This system has a broad potential use in nanocarriers, especially for encapsulating and releasing polar substances in the nonpolar solvents.

研究领域: 材料科学 · 高分子化学
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Polymer Chemistry · 2023 ·Vol. 14 ·期 7 ·888-897 · IF 4.6

Spiropyran-based polymeric micelles in aqueous solution: light-regulated reversible size alterations and catalytic characteristics

Yuting Min,Ruizhen Zhang,Xuli Dong,Lifang Zhang,Dongming Qi,Zan Hua,Tao Chen

A well-defined triblock light-responsive amphiphilic copolymer with nitrospiropyran as the middle block was prepared by reversible addition–fragmentation chain transfer (RAFT) polymerization. The polymeric micelles obtained by self-assembling of the copolymer in water exhibited reversible size changes upon ultraviolet (UV) and visible (Vis)-light irradiation, owing to the transition between the closed three-dimensional spiropyran (SP) and the open planar merocyanine (MC) form, and the corresponding transformation of hydrophobicity and hydrophilicity. The hydrophobic SP form of nitrospiropyran resulted in a larger core diameter, showing higher dye adsorption ability in methyl red adsorption experiments. Upon UV irradiation, the transition of SP to hydrophilic MC caused a decrease of the core diameter, displaying a higher catalytic reaction rate in the Knoevenagel condensation reaction when base-functionalized micelles were applied. This work presented facile light-regulated reversible size changes of polymeric micelles. We expect that the light-regulated strategy developed here would be useful in the fabrication of smart nanoreactors for dye adsorption, catalysis, etc. in a controllable manner.

研究领域: 材料科学 · 化学
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ANALYTICA CHIMICA ACTA · 2019 · IF 5.256

Heating promoted fluorescent recognition of Cu2+ with high selectivity and sensitivity based on spiropyran derivative

Junji Xuan,Jintao Tian

A spiropyran derivative containing an ethyl group ( SPEt ) was applied for fluorescent recognition of Cu 2+ . With Cu 2+ addition, the SPEt -contained solution using a mixed solvent of DMF/H 2 O (9/1, v/v) showed a very strong characteristic emission peak with high quantum yield which is 4.3 times that of the pure SPEt solution. As a result, Cu 2+ was successfully picked out from totally 17 kinds of common metal ions and a detection limit as low as 14.9 fM had been achieved in using this assay system. Particularly, the recognition process was temperature- and time-dependent and could be effectively promoted by heating. In addition, SPEt had been used to image and detect Cu 2+ in mussels. Thus, our results in this study provided an exclusive Cu 2+ recognition via fluorometry in wide temperature, time, and dynamic ranges of assay, enabled a femtomolar scale detection of Cu 2+ by spiropyran derivative, and showed a promising imaging ability of Cu 2+ in marine living organisms.

研究领域: 分析化学 · 生物医学 · 环境科学
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ACS Applied Materials & Interfaces · 2025 · IF 8.2

A Spiropyran-Based Hydrogel Composite for Wearable Detectors to Monitor Visible Light Intensity to Prevent Myopia

Jiaxin Zhang,Mengxia Lu,Xin Cai,Peter Müller-Buschbaum,Qi Zhong

A wearable detector to monitor visible light intensity is realized by the restrained photochromism of a hydrogel composite containing light-responsive spiropyran with hydroxyl groups (SPOH). When exposed to visible light, the SPOH experiences a ring-opening to a ring-closed transition accompanied by discoloration from red to yellow. Unlike in the solution, the photochromism/discoloration rate is strongly correlated to the cross-linking points. By reducing the amount of cross-linker from 40 to 5 mg, the photochromism rate of SPOH is 300% faster. Inspired by the Chinese Jade Loong from Hongshan, the hydrogel composite is shaped into a Loong to monitor the light intensity. By increasing the amount of cross-linker in the head, body, and tail, the photochromism/discoloration rate sequentially turns slower from one region to the other. Higher light intensity is required to realize the discoloration in the hydrogel composite containing a larger amount of the cross-linker. Because the initial colors are identical, the light intensity can be easily traced by checking the discoloration of these pieces containing different amounts of cross-linker. Based on this unique and reversible photochromic capability, the present hydrogel composite can be used for monitoring the visible light intensity to prevent myopia, especially for children and students.

CAS / MDL: 7727-54-0 110-18-9
研究领域: 材料科学 · 生物医学工程 · 光学
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SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY · 2019 · IF 2.931

A near-infrared ratiometric fluorescence probe base on spiropyran derivative for pH and its application in living cells

Kangming Xiong,Caixia Yin,Yongkang Yue,Fangjun Huo

The intracellular pH has a significant effect on several essential biological processes such as material transfer, enzymatic action, cell apoptosis et al. Thus, it is necessary to monitor pH fluctuation in living cells. Here, we designed a near-infrared ratiometric fluorescence probe for pH detection. The spectroscopic responses of probe to pH variations were investigated in CH 3 OH/PBS (v/v, 1:1) mixed solution at different pH values. The experimental results showed that the probe is sensitive to acidity, and the p K a of probe is calculated to be 4.85. When the pH was decreased from 9.0 to 1.0, the color of probe solution change from purple to yellow was found by naked eye. Moreover, the probe can be a practical tool for assessing cellular pH by cell imaging.

研究领域: 生物化学 · 细胞生物学
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NANOTECHNOLOGY · 2024 ·Vol. 35 ·期 33 ·335702 · IF 2.9

A new two-dimensional, spiropyran-based polymer fluorescent nanoprobe with quantitative-fluorescent and photochromic properties for multi-substance detection

Riyan Lin,Hefeng Zhang,Yifu Huang

One challenge of the structural design of a fluorescent probe is how to improve the detection performance on trace target analytes in complex samples. Herein a new polymer fluorescent nanoprobe (2DSP-C28) has been synthesized, by adopting a two-dimensional (2D), spiropyran (SP)-based nanosheet structure with hydrophobic long-chain alkanes (C28). Unlike a traditional SP-based small molecule probe, the 2DSP-C28 probe can exhibit quantitative-fluorescent and photochromic properties. Under the detection of metal-ions, the nanoprobe in dimethyl sulfoxide aqueous solution is selectively fluorescent-quenched-responsive for Fe-ions (∼100 μM), with a characteristic stoichiometric ratio of <10, a high sensitivity (limit of detection: ∼0.2 μM). When the nanoprobe is incorporated into electrospun polyethylene oxide, it can be used for gas detection, and display a color-change with acid-base gas and identify the HF gas. It is expected that this new polymer fluorescent nanoprobe can be promisingly applied for rapidly environmental monitoring on the ion or gas pollution.

研究领域: 材料科学 · 分析化学 · 环境科学
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Alexandria Engineering Journal · 2024 · IF 6.2

Grafting photochromic spiropyran polymer brushes on natural rubber surface via surface-initiated ring-opening metathesis polymerization

Wenya Zhu,Bangsen Li,Jinrui Liu,Shishu Sun,Yan Zhang,Dashuai Zhang,Tianyi Sun,Sumin Zhang,Chen Li,Jianjun Shi,Zaifeng Shi

The modification of stereoregulated functionalized polymers on the surface of natural rubber (NR) is a challenging task. This work provided a practicable grafting method to design photochromic polymer brushes on the NR surfaces using surface-initiated ring-opening metathesis polymerization (SI-ROMP). The designed photochromic polymer brushes were based on norbornenes with spiropyrin (SP) pendents, and grew from the surface of NR films in the presence of Grubbs 2nd catalyst. The results showed that the grafting rate of polymer brushes with photoisomerization structure reached up to 44.91 %. The modified natural rubber (NR-SP) films exhibited rapid coloring/decolorization property under UV irradiation and visible light. This photochromic property initiated by the light-induced isomerisation of the spiropyran structure and the increased surface energy under light stimuli. NR-SP films exhibited stable photochromic characteristics and outstanding anti-fatigue properties after exposing to over six cycles of consecutive UV/Vis irradiation. A simple and practical strategy for the preparation of highly sensitive photochromic natural rubber materials is proposed and provides a potential application in the fields of information storage and anti-counterfeiting.

研究领域: 材料科学 · 高分子化学
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JOURNAL OF MEMBRANE SCIENCE · 2024 · IF 8.4

Spiropyran molecular aggregates implanted photo-responsive graphene oxide membrane with self-cleaning ability for enhanced water purification

Boya Wang,Liguo Shen,Jiujing Xu,Lingya Fei,Bisheng Li,Hongjun Lin,Cheng Chen

Stimuli-responsive separation membranes with adjustable interfacial properties are highly desired for energy-efficient and sustainable water purification , owing to their exceptional antifouling capability and separation selectivity. However, the construction of highly efficient responsive membranes continues to present a substantial challenge. Herein, photo-responsive spiropyran (SP) molecular aggregates obtained via a "good-poor" solvent self-assembly strategy were implanted into lamellar graphene oxide (GO) membrane. The obtained GO/SP membrane with enriched water transport channels and enhanced hydrophilicity demonstrated superior water permeability (95.0 L h −1 m −2 bar −1 ). Benefiting from the reversible photoisomerization of SP molecules between the hydrophobic SP upon light irradiation and the hydrophilic zwitterionic merocyanine (MC) in dark conditions, the GO/SP membrane possessed captivating photo-response property verified by tunable water permeability and molecular rejection. Theoretical calculation revealed that the thermodynamic interface energy between bovine serum albumin (BSA) and membrane surface changed from attraction in dark conditions to repulsion under light conditions. Consequently, the water permeability of BSA-fouled membranes could recover to 96.2 % of its initial level after light irradiation, exhibiting fascinating photo-driven self-cleaning capability. The designed photo-responsive membrane with feasible membrane fouling control holds great promise for efficient water purification .

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

Spiropyran-Decorated Nanoporous Metal–Organic Frameworks for Reversible Light-Controlled Adsorption of Multiple Salts from Water: Implications for Water Purification

Yuhang Liu,Yuanjiang Zhao,Liming Jiang

Herein, we report a kind of light-responsive metal–organic framework (MOF) adsorption material which was fabricated by covalently immobilizing photoactive spiropyran (SP) molecules onto a chromium(III)-based amino-tagged MIL-101 framework through amide linkages. The photoisomerization of SP moieties endows these materials with the unique feature of reversible binding to metal ions. In the dark, the SP-modified MOFs were capable of adsorbing multiple monovalent and divalent salts from saline water and effectively released the adsorbed ions into water upon exposure to simulated sunlight. The SP-modified MOFs showed excellent salt adsorption capacity, of which the MOF with an SP modification ratio of 39% had an ion uptake of 2.27, 1.72, 1.0, 0.8, and 0.39 mmol g–1 for the monocomponent solutions of LiCl, NaCl, KCl, CaCl2, and MgCl2, respectively. After 10 adsorption–desorption cycles, the regenerated adsorbent still exhibited a higher ion adsorption of 1.27 mmol g–1 for the NaCl solution. This work provides a synthetic strategy for salt adsorption materials with nonchemical regeneration ability, which are promising for water desalination and purification.

CAS / MDL: 75-05-8 496-15-1
研究领域: 材料科学 · 环境科学
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INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES · 2025 · IF 8.5

Photo-responsive superhydrophobic cellulose aerogel films from spiropyran and fluorinated modified copolymer brushes through surface-initiated ring-opening metathesis polymerization

Xiaoxue Lin,Jianjun Shi,Zaifeng Shi,Dezhong Zhou

Surface functionalization of natural polymers with polymer brushes is an effective strategy for enhancing their structural and functional properties. Designing spiropyran-based responsive biopolymers is particularly significant for developing smart materials with tunable optical and electronic properties, enabling advanced applications in biointerfaces and biomedical technologies. In this study, we developed a surface-initiated ring-opening metathesis polymerization (SI-ROMP) approach to modify cellulose aerogel films, improving their hydrophobicity and photoresponsiveness. The cellulose aerogel films were fabricated via a water-based solution casting technique and subsequently functionalized with block copolymers of fluorinated polynorbornenes (pNBFn) and spiropyran-modified polynorbornenes (pNbSP). The polymer grafting efficiency reached 28.3 %, influenced by steric hindrance from the side chains. The modified films exhibited enhanced hydrophobicity, thermal stability, and dynamic photoresponsive behavior. Electrochemical impedance spectroscopy indicated that the incorporation of extended π-conjugated spiropyran moieties improved light absorption, charge transfer, and reversibility of optical and electrical properties. Furthermore, the films demonstrated stable and reversible photochromic behavior under visible light irradiation, with long-lasting wettability modulation. These findings highlight the potential of cellulose-based aerogels as multifunctional bio-compatible materials, offering promising applications in optical biosensors, bioimaging, anti-counterfeiting, and UV-responsive display technologies.

研究领域: 材料科学 · 生物医学工程
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