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fluorene
Nature Communications · 2017 ·Vol. 8 ·期 1 ·1-13 · IF 12.124

Fluorene-9-bisphenol is anti-oestrogenic and may cause adverse pregnancy outcomes in mice

Zhang Zhaobin,Hu Ying,Guo Jilong,Yu Tong,Sun Libei,Xiao Xuan,Zhu Desheng,Nakanishi Tsuyoshi,Hiromori Youhei,Li Junyu,Fan Xiaolin,Wan Yi,Cheng Siyu,Li Jun,Guo Xuan,Hu Jianying

Bisphenol A (BPA) is used in the production of plastic but has oestrogenic activity. Therefore, BPA substitutes, such as fluorene-9-bisphenol (BHPF), have been introduced for the production of so-called ‘BPA-free’ plastics. Here we show that BHPF is released from commercial ‘BPA-free’ plastic bottles into drinking water and has anti-oestrogenic effects in mice. We demonstrate that BHPF has anti-oestrogenic activity in vitro and, in an uterotrophic assay in mice, induces low uterine weight, atrophic endometria and causes adverse pregnancy outcomes, even at doses lower than those of BPA for which no observed adverse effect have been reported. Female mice given water containing BHPF released from plastic bottles, have detectable levels of BHPF in serum, low uterine weights and show decreased expressions of oestrogen-responsive genes. We also detect BHPF in the plasma of 7/100 individuals, who regularly drink water from plastic bottles. Our data suggest that BPA substitutes should be tested for anti-oestrogenic activity and call for further study of the toxicological effects of BHPF on human health.

CAS / MDL: 10540-29-1
研究领域: 环境科学 · 毒理学 · 生殖生物学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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INTERNATIONAL JOURNAL OF PHARMACEUTICS · 2022 · IF 6.51

Fluorene methoxycarbonyl-PEG-deferoxamine conjugates “hitchhike” with albumin in situ for iron overload therapy

Linyi Xu,Rou Guan,Bohong Yu,Yicheng Li,Hongzhuo Liu,Yiguo Jiang

Although deferoxamine (DFO) has been approved for the treatment the iron overloaded diseases, its clinical application is impeded by very short circulation time and its relating toxicity. In this work, the fluorene methoxycarbonyl (FMOC) for “albumin hitchhiking” was used to prolong the plasma circulation time of DFO and reduce toxicity. The designed FMOC-PEG-DFO conjugates were found to reversible bind to albumin and gradually release DFO in vivo . Herein, the FMOC-PEG 1000 -DFO conjugates could increase 30 times the blood circulation time of DFO with the improvement of the iron elimination efficacy. Meanwhile, the conjugates markedly reduced the cytotoxicity of DFO. Taken together, the result demonstrated the FMOC-PEG 1000 -DFO conjugates could be a potential therapeutic choice for iron-overload-related diseases.

CAS / MDL: 1185-57-5 9041-08-1
✓ 已验证 产品关联 DOI PubMed 高影响因子
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DYES AND PIGMENTS · 2022 · IF 5.122

Orthogonal conformation regulation enables highly efficient phosphorescence emission in BODIPY-fluorene derivatives without heavy atoms

Yurong Guo,Yue Liang,Yanan Wang,Jingran Zhang,Chao Wang,Yan Sun,Xia Feng,Guangjiu Zhao

The BODIPY-Fluorene derivatives with an orthogonal conformation were prepared for the emission of efficient phosphorescence. The derivatives show visible light absorption (497–513 nm), high phosphorescence quantum efficiency (36.2%) and realize control of luminescence color from green to orange-red. Typical orthogonal conformation and smaller excited state (S 1 and T 4 ) energy gap (0.05 eV) are favorable for intersystem crossing (ISC) process. The calculation are carried out for rationalization between the photophysical properties and conformation of the BODIPY-Fluorene derivatives. We demonstrate that the conformational substitution positions and the distance between D-A are promising strategy to regulate the emission lifetime and quantum efficiency for BODIPY derivatives. Moreover, the ability to generate singlet oxygen was measured by photooxidation of 1,3-diphenylisobenzofuran (DPBF) by singlet oxygen ( 1 O 2 ) photosensitization . At the same time, the LED device displays bright orange-red emission. This work paves the way for further research into the design and application of such materials in advanced optics.

研究领域: 材料科学 · 光学
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NEW JOURNAL OF CHEMISTRY · 2024 ·Vol. 48 ·期 23 ·10497-10506 · IF 2.7

Synthesis and properties of novel block-structured polyarylates containing fluorene: a two-step interface polymerization

Zhoufeng Wang,Yingying Liu,Bolin Wang,Xiubo Long,Wenlong Yao

Random and block polyarylates were synthesized using bisphenol A (BPA), bisphenol fluorene (BHPF), terephthaloyl chloride (TPC), and isophthaloyl chloride (IPC) as raw materials. The synthesis strategies of one-step and stepwise interfacial polymerization methods were adopted. Both types of polyarylates exhibited similar solubility, with block polyarylates showing slightly broader solvent selectivity. The presence of large sterically hindered fluorene groups in BHPF monomers rendered both block and random polyarylates amorphous by restricting the movement of macromolecular segments. The polyarylates demonstrated excellent thermal stability (T5% = around 490 °C) and a high glass transition temperature (Tg > 210 °C). As the covalent bonds of the monomer linkage showed no significant difference, the thermal stability of both types of products was similar. The glass transition temperature increased with an increase in TPC and diefluorene monomer content. The tensile strengths of the random and block polyarylate films ranged from 45.77–69.89 MPa and 49.49–55.29 MPa, respectively, indicating the high tensile strength of the resulting polyarylates. While the block polyarylates did not show significant differences from the conventional properties of random polyarylates, the synthesis of block polyarylates in this study represents a novel attempt, further highlighting the significant influence of the large pendant group of the main chain on the ordered arrangement of molecular segments.

研究领域: 材料科学 · 高分子化学
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DYES AND PIGMENTS · 2026 · IF 3.9

Furan-modified fluorene functionalized chitosan fluorescent hydrogel: preparation and fluorescent sensing toward Fe3+ and Hg2+

Guangxuan Zhu,Chuang Shang,Jiayang Niu,Aiai Gao,Yusen Zhao,Xuegang Chen

The novel furan-modified fluorene-based fluorescent small molecules were synthesized. • A catalyst-free Diels–Alder cycloaddition is utilized to crosslink chitosan, affording a mild fabrication strategy. • The as-prepared fluorescent hydrogel exhibits fluorescence color change behavior under ultraviolet light irradiation. • The fluorescent hydrogel achieve dual detection of Fe 3+ and Hg 2+ in aqueous solutions. In this study, a fluorescent furan-modified fluorene molecule ( F-Fu ) was first synthesized via a Stille coupling reaction. Using F-Fu as a cross-linker, a novel chitosan-based fluorescent hydrogel was successfully prepared through a Diels-Alder reaction between furan-functionalized F-Fu and maleimide-modified chitosan derivatives. The SEM results revealed the hydrogel has a porous network structure with pore sizes ranging from 60 to 100 μm. Rheological characterizations reveal dominant elastic responses (G′>G″), and the elastic modulus is elevated upon increasing crosslinking density. The hydrogel emits blue-violet fluorescence. The main emission peak at 385-386 nm originates from the π-π* transition of the fluorene core, and the shoulder peak at 398-402 nm is attributed to intramolecular charge transfer (ICT). Upon ultraviolet irradiation, the hydrogel exhibits green fluorescence, with its emission peaks merging and undergoing a blue shift to 378-382 nm. In aqueous dispersion, the fluorescence is readily quenched by Fe 3+ and Hg 2+ ions, enabling their sensitive detection. Owing to the paramagnetic or heavy-atom effect upon coordination, the LOD values for Fe 3+ and Hg 2+ are 0.064 ppm and 0.199 ppm, respectively. Download: Download high-res image (304KB) Download: Download full-size image

✓ 已验证 DOI 高影响因子
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Materials Today Communications · 2025 · IF 4.5

Transparent polyamide-imides containing fluorene groups with high glass transition temperature and good dimensional stability

Lei Yang,Jinglei Xing,Xingzhong Fang,Guofei Chen

With the rapid development of the flexible display industry, the requirements for the transparent polyimide flexible substrate are becoming more and more stringent. In this work, two diamines, 9,9-bis(4-(4′-aminobenzoylamino)phenyl)fluorene (FDAADA) and N,N′ -(9,9′-spirobifluorene-2,2′-diyl)bis(4-aminobenzamide) (SBFADA), were synthesized. Cyclopentanone bis-spironorbornane tetracarboxylicdianhydride (CpODA), 4,4′-(hexafluoroisopropylidene)diphthalic anhydride (6FDA), and 9,9-bis(3,4-dicarboxyphenyl)fluorene dianhydride (BPAF) were utilized as dianhydride monomers to prepare a series of transparent polyamide-imides (PAIs). All PAIs exhibited high glass transition temperatures ( T g s) of 423–468 ℃, coefficients of thermal expansion (CTEs) of 36.1–64.2 ppm/K, optical transmittances of 15–85 % at 400 nm, tensile strengths of 89.8–147.4 MPa, and tensile moduli of 2.9–4.3 GPa. In particular, PAI-1 ( T g =454 ℃, T 400 =85 %, CTE=36.1 ppm/K) and PAI-4 ( T g =468 ℃, T 400 =66 %, CTE=50.0 ppm/K) exhibited good optical properties, excellent thermal properties and low CTEs, which demonstrated the potential application in flexible substrate materials.

✓ 已验证 产品关联 DOI 高影响因子
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EUROPEAN POLYMER JOURNAL · 2018 · IF 3.741

Synthesis and resistive switching characteristics of polyimides derived from 2,7-aryl substituents tetraphenyl fluorene diamines

Yanhua Yang,Jingcheng Xia,Zijun Ding,Youxuan Zheng,Shijin Ding,Yingzhong Shen

Four new symmetric diamines (4,4′-(2,7-diphenyl-9H-fluorene-9,9-diyl)dianiline (TPF-Ph), 4,4′-(2,7-bis(4-(naphthalen-1-yl)phenyl)-9H-fluorene-9,9-diyl)dianiline (TPF-Ph-Na), 4,4′-(2,7-di([1,1′-binaphthalen]-4-yl)-9H-fluorene-9,9-diyl)dianiline (TPF-2Na), and 4,4′-(2,7-bis(3,5-dimethoxyphenyl)-9H-fluorene-9,9-diyl)dianiline (TPF-Ph-OMe)) containing tetraphenyl fluorene (TPF) core were synthesized through Suzuki coupling reaction, the corresponding four polyimides (PI(TPF-Ph), PI(TPF-Ph-Na), PI(TPF-2Na), and PI(TPF-Ph-OMe)) were prepared through polymerization reaction. The electrical memory measurement displayed that PI(TPF-Ph) and PI(TPF-Ph-Na) exhibited volatile dynamic random access memory (DRAM) behaviors, PI(TPF-2Na) possessed volatile static random access memory (SRAM) behavior due to the more distorted structure of 1,1′-binaphthalenyl moiety, and PI(TPF-Ph-OMe) showed non-volatile write-once read-many (WORM) behavior due to the presence of deeper charge traps and higher dipole moment of 3,5-dimethoxyphenyl substituent. They possessed low turn-on switching voltages and the ON/OFF current ratios were between 10 3 and 10 5 with the retention times up 4 × 10 3  s. Quantum simulations about energy levels, electrostatic potential (ESP) surfaces, and dipole moment were used to demonstrate the switching mechanism. The experimental results indicated that the electrical memory behaviors of the synthesized polyimides could be tuned through rational structural modification of the electron donor moiety.

CAS / MDL: 98-80-6 89-32-7
研究领域: 材料科学 · 电子工程
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JOURNAL OF MEMBRANE SCIENCE · 2014 · IF 4.908

Fluorene-containing poly(arylene ether sulfone)s as anion exchange membranes for alkaline fuel cells

Pei Yu Xu,Ke Zhou,Guang Lu Han,Qiu Gen Zhang,Ai Mei Zhu,Qing Lin Liu

A series of novel quaternized fluorene-containing poly(arylene ether sulfone)s (APESs) were synthesized. Bromination rather than chloromethylation was used for the conversion of –CH 3 to reactive –CH 2 Br. N,N,N׳,N׳-tetramethyl-1,6-diaminohexane (TMHDA) dissolved in isopropanol (IPA) was used as a quaternization reagent for the preparation of target anion exchange membranes (AEMs). Fourier transform infrared spectroscopy (FT-IR), 1 H NMR spectroscopy and gel permeation chromatography (GPC) were used to characterize the as-synthesized copolymers . The ratio of hydrophilic to hydrophobic monomers was varied to study the structure property of the AEMs. The obtained AEMs were characterized by scanning electron microscopy (SEM) and thermogravimetric analysis (TGA). Water uptake (WU), swelling ratio, ionic exchange capacity (IEC), ionic conductivity , methanol permeability and alkaline stability were also studied. These AEMs have good properties as polymer electrolyte materials with high ionic conductivity (under hydrated conditions) in the range 2.89–8.85×10 −2   S   cm −1 and 5.60–15.64×10 −2   S   cm −1 at 30 and 80   °C, respectively. The methanol permeability of the AEMs in the range 5.99–14.51×10 −8   cm   s −1 is lower than that of Nafion ® 117 (1.82×10 −6   cm   s −1 ). The AEMs show excellent alkaline stability in 1   M KOH solution at 60   °C for a long time. Single cell testing using APES-0.8 showed an open circuit voltage of 0.89   V. A maximum power density of 146   mW   cm −2 at a current density of 423   mA   cm −2 can be achieved at 60   °C. In summary the AEMs are good candidates for evaluation in fuel cell applications .

CAS / MDL: 576-26-1
研究领域: 材料科学 · 能源科学
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HIGH PERFORMANCE POLYMERS · 2019 · IF 1.584

Synthesis and gas transport properties of novel poly(ether ether ketone)s containing fluorene group

Yayun Zheng,Xing Yang,Meng Yuan,Jujie Luo

Two novel gas separation membranes (Phenyl(Ph)-poly(ether ether ketone)s (PEEKs) and PEEKs) based on PEEKs with a high fractional free volume were designed and synthesized. The structure and thermodynamic stability of the membranes were investigated using Fourier transform infrared spectroscopy, proton nuclear magnetic resonance spectroscopy, and thermogravimetric analysis. The two membranes, which were determined to be high-molecular weight polymers by gel permeation chromatography, showed good solubility in a weakly polar solvent. The gas transport properties of the Ph-PEEK membranes were investigated for different gases (CO2, O2, CH4, and N2) at 25°C and 1 atm. The Ph-PEEK-3 membrane with the largest free volume had the largest gas permeability coefficient and maintained good selectivity. The effect of operating temperature on the gas permeation of the Ph-PEEK-3 membrane was also investigated, and the maximum permeability of the four single gases was reached at 55°C and 1 atm.

研究领域: 材料科学 · 化学工程
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Nanoscale · 2019 ·Vol. 11 ·期 14 ·6610-6619 · IF 6.97

From fluorene molecules to ultrathin carbon nanonets with an enhanced charge transfer capability for supercapacitors

Xiaojun He,Xiaoyu Xie,Jingxian Wang,Xiufang Ma,Yuanyang Xie,Jing Gu,Nan Xiao,Jieshan Qiu

It is a big challenge to synthesize ultrathin carbon nanonets with an enhanced charge transfer capability for high-performance energy storage devices. Herein, ultrathin carbon nanonets (UCNs) were successfully synthesized for the first time from fluorene, a typical aromatic molecule, by a template strategy for supercapacitors. The formation mechanism of UCNs was determined using Density Functional Theory and Materials Studio, in which the fluorene-derived radicals were assembled into UCNs in the template-confinement space with the assistance of KOH. The as-made UCNs feature interconnected high-conductivity net-like architectures with enhanced charge transfer capability, evidenced by their high capacitance, excellent rate performance and cycling stability for symmetrical supercapacitors in a KOH electrolyte. This finding may provide a significant step forward in understanding the formation mechanism of graphene-like materials from more complicated aromatic hydrocarbon molecules, and our work may draw wide attention in the fields of aromatic chemistry and carbon-based energy storage materials.

CAS / MDL: 86-73-7
研究领域: 材料科学 · 能源存储技术 · 芳香化学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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SCIENCE OF THE TOTAL ENVIRONMENT · 2022 · IF 10.753

Metagenomic insight of fluorene-boosted sludge acidogenic fermentation: Metabolic transformation of amino acids and monosaccharides

Xiaoxuan Zhou,Tao Liu,Shengyi Zhang,Bo Kang,Xu Duan,Yuanyuan Yan,Leiyu Feng,Yinguang Chen

Fluorene (Flu) occurs widely in various environments and its toxicity to organisms is well-known. However, the impact of Flu on complicated biochemical processes involving functional microbial community has been reported rarely. In this study, the facilitation of Flu on the volatile fatty acids (VFAs) generation executed by acidogenic microbial population during sludge acidogenic fermentation (37 °C, SRT = 8 d, pH = 10.0) was investigated. The accumulation of VFAs (particularly acetic acid) increased initially and then declined with the increasing of Flu concentration (0‐500 mg/kg dry sludge), which reached a maximum (3211.1 mg COD/L) as Flu content was 200 mg/kg dry sludge . The Flu-enhanced VFAs production was primarily attributed to the shift of hydrolysis/acidification, as well as the corresponding functional microbial community and the activity of enzymes. Based on the metagenomics analysis, the conversion of organic substrates, i.e. amino acid and monosaccharide , into VFAs embraced in hydrolysis/acidification shaped by Flu was constructed at the genetic level. The relative abundances of genes included in aminotransfer and deamination process of amino acid and glycolysis of monosaccharide into VFA-precursors (pyruvate, acetyl-CoA and propionyl-CoA), and the further formation of VFAs were improved due to the Flu presence. This study shed light on the Flu-affected microbial processes at the molecular biology level during acidogenic fermentation and was of great significance in resource recovery of sludge containing persistent organic pollutants.

✓ 已验证 产品关联 DOI PubMed 高影响因子
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Colloid and Interface Science Communications · 2022 · IF 5.633

Synthesis and properties of novel crosslinking anion exchange membranes based on quaternary poly(fluorene-piperidine)

Jinyue Zhou,Junjie Chen,Ao Ding,Yiwen Nie,Zhenghan Li,Chunhui Shen,Shanjun Gao

In this work, a novel quaternized poly(fluorene piperidine)(PBBP) without alkaline labile C O bonds is designed and prepared successfully via acid-catalyzed polycondensation reactions. The PBBP-based anion-exchange membranes crosslinked by DBMHDA((AEM-X,X = 1,2,3), BAPTES(AEM-X, X = 4,5,6), BPPO (AEM-7) respectively are prepared and characterized, and the properties of them are analyzed and compared. By crosslinking, AEM-3 and AEM-6 showed obvious microphase separation, resulting in improvement in IEC and ionic conductivity compared to unmodified AEM-0. AEM-3 shows conductivity of 74.7 mS cm −1 at 80 °C. the Si-O-Si network structure provided by BAPTES can effectively promote microphase separation. The IEC of AEM-5 is only 1.45 mmol g −1 , but the ionic conductivity of AEM-5 can reach 60.3 mS cm −1 , which proves the existence of efficient ion channels in the membrane. However, experiments have shown that excessive crosslinking may hinder the transport of OH- and water molecules. BPPO crosslinked AEM-7 showed good mechanical properties and alkaline resistance, while mediocre in other aspects

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