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Spiropyran
RSC Advances · 2020 ·Vol. 10 ·期 45 ·26664-26670 · IF 3.119

Spiropyran-modified upconversion nanocomposite as a fluorescent sensor for diagnosis of histidinemia

Jian Su,Yiwei Li,Wen Gu,Xin Liu

Histidinemia is a congenital metabolic disorder where the histidine (His) metabolism is blocked, resulting in increased concentrations of His in blood and urine. The disease causes an abnormal development of the patient's nervous system, which leads to many serious illnesses. Therefore, it is very important to diagnose early. In this study, we developed a novel fluorescent nanosensor NaGdF4:Yb3+, Er3+@SiO2–spiropyran (UCNP@SiO2–SP). The nanosensor displayed a “turn-off” fluorescence response towards His. When His was mixed with UCNP@SiO2–SP, His could specifically bind to SP, which could cause the isomerization of SP. The structure of SP was changed from spiroform into merocyanine form. The luminescence of the sensor was overlapped with the absorption of the merocyanine form. As a result, His will lead to fluorescence quenching of the sensor based on inner filter effects (IFE), which can be used to detect His. Importantly, as the first report of a UCNP@SiO2–SP nanosensor for detecting His, this method exhibits good selectivity and anti-interference capability. The detection limit is 4.4 μM. In addition, the amount of His in urine was also measured, suggesting the applicability of this sensor for histidinemia diagnosis.

研究领域: 医学诊断 · 生物化学 · 纳米技术
✓ 已验证 DOI PubMed 高影响因子
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Journal of Materials Chemistry B · 2023 ·Vol. 11 ·期 39 ·9525-9531 · IF 7

A spiropyran-decorated nanocoating for dynamically regulating bacteria/cell adhesion and detachment

Jie Li,Zhuang Ma,Anran Li,Siyuan Huang,Yufei Zhang,Yun Xue,Xianhui Song,Ye Zhang,Shihao Hong,Mo Wang,Zhongming Wu,Xinge Zhang

Microorganism adhesion and the resulting contamination of the biomaterial is one of the major causes of biomedical device failure. Stimuli-responsive materials based on dynamically regulating interactions with reversible characteristics of on–off states have attracted increasing attention. Here, a facile self-assembled biomaterial nanocoating constructed using acidity- and photoregulated spiropyran-modified nanoparticles was developed for reversibly regulating bacteria or mammalian cell adhesion-and-detachment. The coating was formed by coating a solution of spiropyran-conjugated nanoparticles around the surface of a silica gel followed by curing and drying at 60 °C for 30 min. Importantly, efficient adhesion-and-detachment of bacteria or cells could be controlled even after 8 cycles owing to the excellent acidity- and light-switched ability. Collectively, this well-defined self-assembled nanocoating as a dynamical and reversible agent provides promising insight for the development of biomedical devices, especially for biomaterial medical coatings.

研究领域: 生物材料学 · 表面工程 · 微生物学 · 再生医学 · 抗菌技术
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JOURNAL OF POLYMER RESEARCH · 2025 ·Vol. 32 ·期 5 ·1-14 · IF 2.8

Photochromic functionalization of polyetheramine-cured epoxy resin based on spiropyran derivatives doping

Xu Zijie,Liu Xingyao,Yu Chongwen,Fan Xinyu,Yan Zhongwei,Xiao Haotian,Song Yujie,Xu Jian

Despite being a widely used polymer material, studies on the spiropyran (SP)-derived photochromic functionalization of amine-cured epoxy resin materials are not sufficiently detailed. Traditional amine-based curing agents can undergo chromogenic reactions with SP through multiple reaction mechanisms. Furthermore, the dense crosslinked network structure of the resin restricts the conformational isomerization of SP, thereby leading to the failure of photochromic functionalization in epoxy resin systems. In this work, a SP derivative (YBSP), which contains a meta-dinitrobenzene structure, was synthesized and doped into polyetheramine-cured epoxy resin materials. Polyetheramine does not react with SP to form small molecular fragments, and the bulky side group of YBSP provides sufficient free volume for its isomerization in the resin crosslinking structure. As a result, the resin material doped with YBSP exhibits photochromic properties after exposure to 365 nm UV light, and as the YBSP content increases, the fracture toughness of the resin is enhanced, with its fracture strength reaching 72.815 MPa. In conclusion, doping YBSP into epoxy resin not only imparts photochromic functionality to the material but also enhances its toughness while maintaining its original thermodynamic properties.

研究领域: 材料科学 · 化学工程
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ACS Applied Materials & Interfaces · 2024 · IF 8.3

Photochromic Spiropyran-Based Dual-Emitting Luminescent Hybrid Films for Dynamic Information Anticounterfeiting

Ziyi Bai,Lei Guo,Di Zhao,Yige Wang

Photoluminescent materials are widely used for information storage and anticounterfeiting, while most of them have the disadvantages of static information performance and weak processability, which is still a challenging task in developing dynamic anticounterfeiting materials with high security levels. Herein, we fabricated a novel photostimuli-responsive dual-emitting luminescent material UPTES-SPn-Tb-hfa, which was obtained by introducing the photochromic molecule spiropyran (SP) and lanthanide complex (Tb-hfa) into a siloxane-polyether matrix using the sol–gel process. Due to the conformation-dependent photochromic fluorescence resonance energy transfer between the Tb-hfa donor and SP acceptor, the ring-closing (SP)/ring-opening (MC) isomerization of the SP unit leads to a reversible luminescence switching in UPTES-SPn-Tb-hfa. This composite material has great potential for advanced anticounterfeiting because of the advantage of rapidly repeatable encryption/decryption for at least 8 times and dynamic luminescent colors within 15 s. In addition, due to its two luminescent centers (Tb3+ and MC), the luminescent color of this material can be regulated by 254 and 365 nm UV-light irradiation, which facilitates the design of multicolored anticounterfeiting labels. Our work presents a novel design methodology to fabricate dynamic anticounterfeiting materials, significantly enhancing the security of anticounterfeiting applications.

CAS / MDL: 24801-88-5
研究领域: 材料科学 · 光学 · 化学
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DYES AND PIGMENTS · 2021 · IF 4.889

Synthesis and photochromic behavior of comb-like acrylate polymer nanoparticle containing spiropyran

Yan Gao,Qing Yin,Xiaoye Geng,Xingxiang Zhang,Wei Li,Y. Gao,X. Geng,X. Zhang,W. Li

Spiropyran (SP) materials have attracted considerable interest owing to sensitive and efficient photochromic properties, but it is a challenge to obtain photochromic materials with excellent sensitive UV-responsivity and photodegradation resistance durability. In this study, a series of comb-like acrylate polymer nanoparticle latexes containing SP are fabricated via miniemulsion polymerization. The influence of the length of the alkyl side chain of comb-like acrylate polymer on some photochromic properties of SP is investigated. Compared with the short-side chain poly(butyl acrylate) (PBA) nanoparticles latexes, the comb-like acrylate polymer nanoparticle latexes with longer side chain possess better photoresponsivity and more excellent photodegradation resistance because the strong interaction and chain flexibility of comb-like alkyl side chain provide effective spaces for the SP→MC or MC→SP photochemical isomerization . The investigations of photochromic nanoparticle latexes guide an approach to reversible optical data storage, multipurpose photo-responsive sensing system and show promising application in the field of ultraviolet intensity indicator and flexible wearable UV protective clothing.

CAS / MDL: 94-36-0
研究领域: 材料科学 · 高分子化学 · 光学材料
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JOURNAL OF RHEOLOGY · 2017 ·Vol. 61 ·期 1 ·107-116 · IF 3.136

Rheology of a spiropyran functionalized hydrophobically modified ethoxylated urethane in aqueous solution

Dong Renfeng,Peng Jun,Chang Xueyi,Zhang Qilu,Hong Liangzhi,Ren Biye

Hydrophobically modified ethoxylated urethanes (HEURs) have been widely used as effective thickeners for improving the solution rheological properties in a variety of applications for over 40 years. We designed and prepared a novel photosensitive spiropyran-functionalized HEUR polymer ( SP-HEUR ), which was used to investigate the influence of hydrophobicity change of hydrophobes induced by photoisomerization of spiropyran (SP) group on the solution aggregation and rheological properties. The concentrated SP-HEUR solutions show an interesting photoresponsive rheological behavior upon alternative exposure to ultraviolet and visible light due to a reversible SP- to merocyanine-form conversion and back. A reversible rearrangement of micellar junctions through loop-bridge or bridge-loop transitions is proposed to interpret the influence of photoisomerozation of spiropyran groups on the associative structure and rheological properties of the polymer solution. This work will not only provide new insights into the influence of hydrophobicity change of hydrophobes on the associative structure and rheological properties of HEUR solutions but also opens a new perspective for the development of some special applications of HEURs in the manufacturing and transmission of soft materials, waterborne coating, inks, medicines, cosmetics, and so on.

CAS / MDL: 77-58-7
研究领域: 材料科学 · 化学工程 · 软物质物理
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Polymers · 2021 ·Vol. 13 ·期 15 ·2496 · IF 4.329

Photochromic Polyamide 6 Based on Spiropyran Synthesized via Hydrolyzed Ring-Opening Polymerization

Shiyou Tian,Jicong Zhang,Qiong Zhou,Limei Shi,Wenwen Wang,Dong Wang

We report photochromic polyamide 6 (PA6) which was synthesized by hydrolyzed ring-opening polymerization of ε-caprolactam with spiropyran (SP) embedded in the polymer chains. It indicated that crystallinity degree of the resulting copolymers was decreased since only PA6 segments can crystallize with increasing content of SP modifier. Meanwhile, toughness of photochromic PA6 was decreased. The photochromic property analysis indicated that the sample with more flexibility and more content of SP was more sensitive to UV light at the beginning of irradiation than other samples and its color after being irradiated for 1 min tended to reddish. Investigation revealed that the UV-vis absorbance of SP-PA6-3 had negligible decay after 10 cycles, which indicated SP-modified PA6 possessed excellent photoresponse reversibility and fatigue resistance.Keywords:photochromic;polyamide 6;spiropyran;structure and properties

研究领域: 材料科学 · 高分子化学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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LUMINESCENCE · 2022 ·Vol. 37 ·期 11 ·1891-1898 · IF 2.613

Aldehyde spiropyran fluorescent probe for rapid determination of hydrazine in environmental water

Xianzhi Huang,Ziqiang Zhou,Xiaohua Xiao,Ling Xia,Gongke Li

Hydrazine often receives publicity because it has a wide range of applications but high toxicity at the same time. Here, we invented a novel aldehyde spiropyran fluorescent probe (SP-CHO) for fluorescence determination of hydrazine. The probe was synthesized through a hydrolysis reaction and a condensation reaction. It exhibits a specific response to hydrazine. The influence factors and anti-interference ability of SP-CHO identifying hydrazine were studied. HRMS, 1 H NMR, and density functional theory (DFT) calculations were used to reveal the recognition mechanism. Results showed that SP-CHO can be used for fluorescence determination of hydrazine with high selectivity and sensitivity. An SP-CHO-based fluorescence method was established for quantitation of hydrazine. The detection limit was 1.26 μmol/l, and the linear range was 5–100 μmol/l. The determination of hydrazine in water samples can be completed within 10 min, which shows good application prospects in real-time detection and process monitoring.

研究领域: 环境科学 · 分析化学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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Journal of Materials Chemistry C · 2018 ·Vol. 6 ·期 8 ·2113-2122 · IF 5.976

Non-invasive fluorescence switch in polymer films based on spiropyran-photoacid modified TPE

Qi Yu,Xing Su,Ting Zhang,Yu-Mo Zhang,Minjie Li,Yifei Liu,Sean Xiao-An Zhang

Non-invasive fluorescent molecular switch is very challenging to achieve in solid state. Here, a new multi-stimulus-responsive fluorescent molecular switch of SPPATPE was prepared by linking spiropyran-photoacid (SPPA) with tetraphenylethene (TPE). The isomerization of SPPATPE can be triggered with either visible light/dark or acid/base in solution. Both ring-closed form (RCF) and ring-open form (ROF) of SPPATPE exhibit aggregation-induced emission (AIE). The RCF SPPATPE aggregates give out a cyan emission, which is assigned as the local excited emission of TPE moiety, while ROF SPPATPE have two forms of aggregation states, which give out two red emissions from intramolecular charge transfer. By selecting a suitable polymer of polyvinyl pyrrolidone (PVP) as the matrix, which gives the molecules a moderate alkaline environment, SPPATPE can exhibit non-invasive light/heat responsive emission switch in the polymer thin film with both good waterproofness and good processibility, which makes this kind of hybrid material potentially applicable in photo sensing, rewritable display, etc.

CAS / MDL: 100-97-0
研究领域: 材料科学 · 光学
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POLYMER · 2022 · IF 4.432

Intrinsic healable mechanochromic materials via incorporation of spiropyran mechanophore into polymer main chain

Xiaoke Song,Yan Song,Xurui Cui,Jun-Peng Wang,Yang Luo,Tao Qi,Guo Liang Li

The development of multifunctional self-healing materials is highly demanding. Herein, an intrinsic healable mechanochromic (i-HMC) material was synthesized via the incorporation of spiropyran mechanophore into the polymer main chain. The as-synthesized i-HMC material exhibited mechanically induced color change as well as great self-healing performance. The mechanical properties of the damaged sample can be completely restored with a high healing efficiency of 98.3% and great toughness of 447 MJ/m 3 . The mobility behaviors of the polymer chain and hydrogen bonding interaction were analyzed through rheological measurements and in-situ FT-IR. The as-synthesized intrinsic materials are capable of dynamic, yet tough healable mechanochromic functions. In contrast to the composites, the intrinsic healable mechanochromic materials contain no foreign additives, which are highly potential for future applications in structural health detectors, load-bearing elements, and wearable devices .

CAS / MDL: 822-06-0
研究领域: 材料科学 · 高分子化学
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JOURNAL OF PHOTOPOLYMER SCIENCE AND TECHNOLOGY · 2019 ·Vol. 31 ·期 6 ·739-746 · IF 0.934

Synthesis of Water-Soluble Spiropyran-Modified Poly(acrylic acid) Micelles and Their Optical Behaviors

Rui Xue,Xinghua Zhang,Jintao Tian

In this study, a spiropyran derivative (SPOH) is firstly grafted onto a polymer backbone of a poly(acrylic acid) (PAA) via an esterification process. The synthesized spiropyran-modified poly(acrylic acid) (PAA-SP) polymer is characterized by FTIR and 1H NMR. The synthesized PAA-SP is then dissolved into water to achieve water-soluble micelles. The optical behaviors of PAA-SP micelles are investigated by ultraviolet-visible (UV-Vis) absorption spectra and fluorescence emission spectra under acid/base and light stimuli in aqueous solution. Our experimental results reveal that the as-prepared PAA-SP micelles are water-soluble and show good photochromic and emissive behaviors. Meanwhile, the optical behaviors of the micelles are light-responsive and acid/base-responsive and hence can be tailored via the adjustments of both light and pH value of the solution sample. And our results may be meaningful for practical application of hydrophobic spiropyran derivatives in aquatic environments.

研究领域: 材料科学 · 化学
✓ 已验证 DOI 高影响因子
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JOURNAL OF POLYMER RESEARCH · 2019 ·Vol. 26 ·期 4 ·1-11 · IF 1.53

Dual responsive spiropyran-ended poly(N-vinyl caprolactam) for reversible complexation with metal ions

Yang Zhouxiaoshuang,Wang Feng,Liu Hui

With the spiropyran-containing compound as the initiator, dual responsive spiropyran-ended poly(N-vinyl caprolactam) (SP-PNVCL) was synthesized by atom transfer radical polymerization. The structure of the resulting polymer was characterized by 1 H NMR and gel permeation chromatography, and the polymer had both reversible light-responsive and thermo-sensitive behaviors. Metal ions could be bound between merocyanine formed by photoisomerization of spiropyran and the amino group of N-vinyl caprolactam unit through synergetic coordination. The complexation of SP-PNVCL with several metal ions was investigated by UV-Vis absorption spectroscopy, and it was found that SP-PNVCL might be used as a potential recognition probe for Fe 2+ , accompanied by obvious color change from colorless to brown by naked eye. The detection limit and photo-reversible recyclable behaviors of SP-PNVCL for Fe 2+ were also investigated in details. The kind of spiropyran-ended poly(N-vinyl caprolactam) had great application potential in environment protection and biological area.

研究领域: 高分子化学 · 环境科学 · 生物医学工程 · 分析化学 · 材料科学
✓ 已验证 DOI 高影响因子
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