JOURNAL OF CHEMICAL RESEARCH
·
2016
·
IF 0.661
Haidong Liu,Bo Chen,Jin Cai,Junqing Chen,Min Ji
Eleven trifluoromethylated amines were synthesised in high yield (up to 98%) under metal-free and oxidant-free conditions using iminium salts as starting material and the addition of trifluoromethyltrimethylsilane in dimethylformide containing potassium fluoride.
研究领域:
有机化学
·
合成化学
✓ 已验证
DOI
高影响因子
SYNTHESIS-STUTTGART
·
2025
·
IF 2.3
Lulu Qin,Tao Yu,Zhengwei Ding,Min Zhao,Pengfei Li
A highly efficient protocol for the synthesis of trifluoromethyl-substituted cyclopentanes, a structural motif ubiquitous in bioactive compounds and natural products, via boron-radical-catalyzed (3+2) cycloaddition of aroylcyclopropanes and trifluoromethyl-substituted alkenes was developed. Employing readily available precursors, this modular, atom-economical, metal-free, and operationally simple process was compatible with diverse functional groups, giving the products in generally good to high yields. Trifluoromethyl-substituted bicyclo[2.1.1]hexanes (BCHs) were analogously prepared.
研究领域:
有机化学
·
药物化学
✓ 已验证
DOI
高影响因子
JOURNAL OF GENERAL AND APPLIED MICROBIOLOGY
·
2020
·
IF 1.442
Nengqiang Wang,Zhen Luo,Kaiqin Li,Yingcui Xu,Cheng Peng
A strain LZ1, which showed efficient asymmetric reduction of 3,5-bis(trifluoromethyl) acetophenone to enantiopure (S)-[3,5-bis(trifluoromethyl)phenyl]ethanol, which is the key intermediate for the synthesis of a receptor antagonist and antidepressant, was isolated from a soil sample. Based on its morphological, 16S rDNA sequence, and phylogenetic analysis, the strain LZ1 was identified to be Sphingomonas sp. LZ1. To our knowledge, this is the first reported case of the species Sphingomonas exhibiting stricter S-enantioselectivity and its use for the asymmetric reduction of 3,5-bis(trifluoromethyl) acetophenone. Some key reaction parameters involved in the bioreduction catalyzed by whole cells of Sphingomonas sp. LZ1 were subsequently optimized, and the optimized conditions for the synthesis of (S)-[3,5-bis(trifluoromethyl)phenyl]ethanol were determined to be as follows: phosphate buffer pH 7.5, 70 mM of 3,5-bis(trifluoromethyl) acetophenone, 30 g/L of glucose as a co-substrate, 300 g (wet weight)/L of resting cell as the biocatalyst, and a reaction for 24 h at 30°C and 180 rpm. Under the above conditions, a best yield of 94% and an excellent enantiomeric excess of 99.6% were obtained, respectively. Sphingomonas sp. LZ1 could also asymmetrically reduce a variety of prochiral ketones to their corresponding optical alcohols with excellent enantioselectivity. These results indicated that Sphingomonas sp. LZ1 had a remarkable capacity to reduce 3,5-bis(trifluoromethyl)acetophenone to its corresponding (S)-[3,5-bis(trifluoromethyl)phenyl]ethanol, and might be a new potential biocatalyst for the production of valuable chiral alcohols in industry.
研究领域:
微生物学
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生物催化
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有机合成
✓ 已验证
DOI
PubMed
高影响因子
ACS Omega
·
2020
·
IF 2.87
Tian Tian,Zhiming Zhu,Yalong Ding,Guoli Li,Nan Li,Tong Shen
The first total synthesis of sanjoseolide (1), which was originally obtained from Dalea frutescens A, was achieved via an efficient route with a longest linear sequence of six steps from the commercially available 2,4-dihydroxyacetophenone in 8.6% overall yield. Meanwhile, a series of sanjoseolide representative analogues were synthesized and assessed for their antiproliferative potency against cancer cells of different origins. Compound 8e inhibited the survival of all tested cancer cell lines in a dose-dependent manner, the IC50 values of the treatment were about 12.8 μM for human cholangiocarcinoma cell lines RBE and 12.7 μM for human cholangiocarcinoma cell lines HCCC-9810, which was more active than sanjoseolide (1). Analysis of the structure–activity relationships revealed that the presence of a trifluoromethyl group may be beneficial in terms of both RBE and HCCC-9810 inhibition.
研究领域:
有机化学
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肿瘤学
·
药物化学
✓ 已验证
DOI
高影响因子
MOLECULES
·
2024
·Vol. 29
·期 23
·5622
·
IF 4.2
Shengxue Zhang,Wangchuan Xiao,Jingjing Wu,Fanhong Wu,Houjin Huang,Xiaoyu Ma,Yafei Shi,Chao Liu
A novel and efficient 1,2-oxidative trifluoromethylation of olefins employing Ag(O 2 CCF 2 SO 2 F) as a trifluoromethyl source is described with O 2 as the oxidant, which provides access to a variety of valuable α-trifluoromethyl-substituted ketones. The broad substrate scope, feasibility of large-scale operation, and derivatization reactions of α-trifluoromethyl ketones demonstrate the promising utility of this protocol.
研究领域:
有机化学
·
合成化学
✓ 已验证
DOI
PubMed
高影响因子
Polymers
·
2023
·Vol. 15
·期 13
·2853
·
IF 5
Yurong Zhang,Haidan Lin,Kai Dong,Shasha Tang,Chengji Zhao
A series of epoxy resins containing various trifluoromethyl groups were synthesized and thermally cured with diaminodiphenylmethane (DDM) and aminophenyl sulfone (DDS). All epoxy resins exhibited excellent thermal stability with the glass transition temperatures of above 128 °C and 5% weight loss temperatures of above 300 °C. DDS-cured epoxy resins possessed higher thermal stability than that of DDM-cured epoxy resins, while DDM-cured epoxy resins showed better mechanical, dielectric, and hydrophobic properties. Additionally, DDM-cured epoxy resins with different locations and numbers of trifluoromethyl groups showed flexural strength in the range of 95.55~152.36 MPa, flexural modulus in the range of 1.71~2.65 GPa, dielectric constant in the range of 2.55~3.05, and water absorption in the range of 0.49~0.95%. These results indicate that the incorporation of trifluoromethyl pendant groups into epoxy resins can be a valid strategy to improve the dielectric and hydrophobic performance.Keywords:trifluoromethyl substitution;low dielectric constant;hydrophobicity;thermal stability
研究领域:
材料科学
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化学工程
✓ 已验证
产品关联
DOI
PubMed
高影响因子
Current Protocols
·
2024
·Vol. 4
·期 1
·e956
·
IF 0
Xuan Chen,Long Xie,Chenglong Zhang,Shen Tian,Zeyu Tang,Ming Xiang,Weiwei Tian,Patrick Lu,Xianbin Yang
The integration of fluorine atoms into biologically active organic compounds has proved to be a vital technique in small molecule drugs. This technique can substantially enhance crucial properties, including metabolic stability, lipophilicity, and bioavailability, often with a mere addition of a single fluorine atom or a trifluoromethyl group. Over the past few decades, this concept has also been applied in nucleic acid chemistry. A commonly employed 2′-OH substitution is the introduction of a 2′-deoxy-2′-fluoro (2′-F) group. The strong electronegativity of fluorine prompts the modified siRNA to readily adopt a C3′- endo conformation, resulting in significant advantages in terms of binding affinity. To enrich the toolbox of chemical modification of oligonucleotides, the replacement of the 2′-OH with the 2′- O -trifluoromethyl group has been developed in RNA analog synthesis. Oligodeoxynucleotides containing the 2′- O -trifluoromethyl group can greatly increase the thermal stability of DNA/RNA duplexes depending on the position and amount of the modification. Moreover, 2′- O -trifluoromethylated oligodeoxynucleotide also exhibited a slightly higher resistance to snake venom phosphodiesterase than the unmodified oligodeoxynucleotide. The 2′- O -trifluoromethylated oligonucleotides can emerge as a label to study RNA structure and function as well, or to develop DNA/RNA-based diagnostics. Hence, it is necessary to report an effective method for the synthesis, deprotection, purification, and characterization of oligonucleotides bearing a 2′ -O -trifluoromethyl group. © 2024 Wiley Periodicals LLC. Basic Protocol 1 : Preparation of 6- N -benzoyl-5′- O -dimethoxytrityl-2′- O -trifluoromethyl adenosine 3′-(2-cyanoethyl N,N -diisopropyl)phosphoramidite Basic Protocol 2 : Preparation of 4- N -acetyl-5′- O -dimethoxytrityl-2′- O -trifluoromethyl cytidine 3′-(2-cyanoethyl N,N -diisopropyl)phosphoramidite Basic Protocol 3 : Preparation of 2- N -isobutyryl-5′- O -dimethoxytrityl-2′- O -trifluoromethyl guanine 3′-(2-cyanoethyl N,N -diisopropyl)phosphoramidite Basic Protocol 4 : Preparation of 5′- O -dimethoxytrityl-2′- O -2-trifluoromethyl uridine 3′-(2-cyanoethyl N,N -diisopropyl) phosphoramidite Basic Protocol 5 : Solid-phase synthesis of 2′- O -trifluoromethylated RNA analogs Basic Protocol 6 : Deprotection and purification of 2′- O -trifluoromethyl-RNAs
研究领域:
生物有机化学
·
核酸化学
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药物化学
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RNA生物学
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分子生物学
·
药学
✓ 已验证
DOI
ACS Applied Materials & Interfaces
·
2025
·
IF 8.2
Long Ni,Cuiqing Zhou,Lu Shen,Ke Yang,Yinfu Luo,Liwei Yan,Shuang Xia,Mei Liang,Shengtai Zhou,Huawei Zou
Lightweight porous materials with integrated cushioning and shock absorption, excellent thermal insulation, and hydrophobicity demonstrate a broad application prospect in high-end engineering sectors. Herein, the fabrication of lightweight polyimide foams (PIFs) containing trifluoromethyl and siloxane moieties was proposed by adopting copolymerization and microwave-assisted foaming processes. The synthesis and preparation of fluorine- and silicon-containing polyester ammonium salt (PEAS) precursor powders and subsequent PIFs, as well as the relationship and mechanism between structure and properties, were systematically explored. The construction of the anisotropic pore structure was attributed to the “bottom-up” directional foaming behavior of the microwave-assisted foaming process, which endowed PIFs with different traits with respect to the pore growth direction. The resulting copolymerized PIFs displayed low density (18.3–27.7 kg/m3), enhanced mechanical flexibility (compressive strength improvement of 26.2%, compression response rate between 97.5 and 99.1%), excellent thermal stability (T5% > 485.2 °C), and thermal insulation performance. Combining the micro/nano pore structure with the presence of hydrophobic trifluoromethyl and siloxane moieties, PIFs exhibited exceptional hydrophobicity with the water contact angle, reaching as high as 145.9° in the vertical direction (parallel to pore growth direction) and 136.3° in the horizontal direction (perpendicular to pore growth direction). Therefore, lightweight, mechanically flexible, thermally insulating, and hydrophobic PIFs were successfully prepared by the proposed approach, which demonstrate potential applications in the aerospace, transportation, microelectronics, and nuclear energy sectors, among others.
研究领域:
材料科学
·
化学工程
✓ 已验证
产品关联
DOI
PubMed
高影响因子
EUROPEAN POLYMER JOURNAL
·
2025
·
IF 6.3
Jinglei Xing,Lei Yang,Tianci Ma,Xingzhong Fang,Guofei Chen
Colorless polyimide (CPI) films have good application prospects in flexible optoelectronic devices due to their excellent heat resistance and transparency. In this study, a diamine monomer containing a terphenyl skeleton and CF 3 group substituted at ortho -position of amino group, 1,4-bis(3-(trifluoromethyl)-4-aminophenyl)benzene (6FTD), was successfully designed and synthesized, and a series of corresponding polyimides (PIs) were obtained by copolymerization of 4,4′-(hexafluoroisopropylidene)diphthalic anhydride (6FDA), 6FTD and 2,2′-bis(trifluoromethyl)benzidine (TFDB). The introduction of rigid and linear terphenyl structure in 6FTD was beneficial to improve the heat resistance and mechanical properties of PI films. In addition, the CF 3 group derived from 6FTD effectively inhibited the rotation between the imide ring and the benzene, so that the 6FTD-containing PI film had a high glass transition temperature ( T g ). At the same time, the CF 3 groups caused a large free volume between molecular chains, which ensured the excellent optical transparency and solubility. In particular, PI-50 exhibited high T g of 399°C, transmittance of 82 % at 450 nm, tensile strength of 146 MPa and tensile modulus of 3.9 GPa. These results indicate that the design of rigid skeleton and side group provides an effective method for developing heat-resistant transparent PI.
研究领域:
材料科学
·
高分子化学
✓ 已验证
产品关联
DOI
高影响因子
Surfaces and Interfaces
·
2024
·
IF 5.7
Fangfang Shang,Hengdao Quan,Xiaoxun Ma
In this study, 3-trifluoromethylpyrazole (TMPZ) was developed as a multifunctional electrolyte additive to enhance wettability between separator and electrolyte, CEI formation and remove HF to improve the performance of Li/NCM622 batteries by experiment and theoretical calculation. After 200 cycles at 30 °C, the discharge capacity retention of batteries at 1 C with 0.5 wt% TMPZ additive is remarkably enhanced from 68.3 % to 83.2 %. The enhanced electrochemical performance of the batteries by adding TMPZ additive is evaluated by the spectroscopic characterization and theoretical calculation. It is demonstrated that TMPZ can generate uniform and dense CEI film via ring-opening electrochemical polymerization of TMPZ on the NCM622 electrode surface. The CEI film helps to suppress the breakdown of LiPF 6 electrolyte and the leaching of transition metals, effectively avoiding harmful side reactions between the NCM622 electrode and the electrolyte. Furthermore, introducing TMPZ can enhance the wettability between separator and electrolyte, therefore providing more channels of Li + to accelerate reaction kinetics of batteries.
研究领域:
材料科学
·
电化学
✓ 已验证
产品关联
DOI
高影响因子
EUROPEAN POLYMER JOURNAL
·
2024
·
IF 5.8
Jingwei Jiang,Yunlong Sun,Zhipeng Wang
With the rapid growth of 5G communication technology, low-dielectric materials can decrease the loss of the signal during transmission. Hence, there is an urgent need to develop high-performance materials with low dielectric constant (D k ) and dielectric loss (D f ) at high frequency. In this study, we propose a strategy that combines bulk rigid quinoxaline structure and low polarizability trifluoromethyl group to prepare poly (aryl ether)s (PAEs) with low D k and D f at high frequencies. The effect of methyl substituents on the properties of PAEs was focuses on investigated. Accordingly, three difluoro-monomers containing quinoxaline structures were designed and prepared and novel quinoxaline-based PAEs with different numbers of methyl substituents were synthesized by nucleophilic condensation reactions with the bisphenol monomer hexafluorobisphenol A (BP6F). Test results that the resultant PAEs exhibited excellent thermal and solubility properties, with 5 % thermal decomposition temperatures ( T d5% ) in the range of 500−515 °C and glass transition temperatures ( T g ) reaching 225 °C. Furthermore, these PAE films show outstanding optical transparency, with cut-off wavelengths of 398−400 nm and above 87 % transmission at 800 nm. Most importantly, the novel PAE films possess ultra-low D k and D f , with the lowest values reaching 2.45 and 0.0024 at 10 GHz and maintain low water absorption (0.53–0.63 %). The excellent properties of novel quinoxaline-based PAEs provide its application potential in the field of high-frequency communications.
研究领域:
材料科学
·
高分子化学
✓ 已验证
产品关联
DOI
高影响因子
EUROPEAN POLYMER JOURNAL
·
2021
·
IF 4.598
Kaitai Hu,Qingqing Ye,Yingtao Fan,Junyi Nan,Fangyuan Chen,Yang Gao,Yingzhong Shen
Polyimide (PI) films have excellent comprehensive properties and bright prospects in the next generation of optoelectronic and microelectronic applications. PIs were synthesized by aromatic diamines and alicyclic dianhydrides considered to be the most effective method for preparing polyimides with high light transmittance and low dielectric constant. In order to improve the overall performance of polyimide, the introduction of a large trifluoromethyl group into the main chain is also considered a powerful strategy. In this article a novel diamine containing 6 trifluoromethyl groups has been designed and synthesized by Suzuki reaction. Afterwards, PIs were synthesized with fluorinated aromatic dianhydride and alicyclic dianhydride through a two-step method. The two PIs have excellent solubility: PI-a and PI-b exhibited excellent solubility in common polar solvents. Such as DMF, DMAc, NMP and DMSO at room temperature, and PI-a was soluble in low-boiling solvents such as ethyl acetate, CH 2 Cl 2 and CHCl 3 at room temperature. PI-b was soluble in low-boiling solvents acetone and CHCl 3 at room temperature, which was rarely seen in other aromatic polyimides. Soluble in common organic solvents, especially low boiling point solvents, made these polymers easy to process and suitable for processing technology in solution. This was an important modification for PIs. They also showed good high temperature resistance: the decomposition temperature (T 5% ) of two PIs were 520 °C and 475 °C. In addition, the residual rate at 790 °C was 50% and 49% respectively. Two PI films had a very low dielectric constant 2.26 and 2.24, respectively, which was attributed to the hyperbranched structure and strong electron-withdrawing fluorine-containing groups. PI-a and PI-b also had low water absorption of 0.66% and 0.72%, respectively. The transmittance of PI-a and PI-b high transparent films at 450 nm were 74% and 82%, respectively. The significant optical modification was mainly due to the weak electron-accepting alicyclic unit and the large trifluoromethyl electron withdrawing group. This work mainly provided an effective strategy for synthesizing comprehensive excellent performance PIs with high transmittance, excellent solubility, low water absorption, high heat resistance and low dielectric constant.
研究领域:
材料科学
·
光学电子学
✓ 已验证
产品关联
DOI
高影响因子
危险品化学品经营许可证（带存储）