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NEW JOURNAL OF CHEMISTRY · 2017 ·Vol. 41 ·期 16 ·7908-7914 · IF 3.269

A direct crossed polymerization of triphenylamines and cyclohexanones via CC bond formation: the method and its bioimaging application

Hengchang Ma,Haiying Cao,Lei Lei,Zengming Yang,Manyi Yang,Yanfang Qin,Yucheng Ma,Xiaolin Guan,Dedai Lu,Ziqiang Lei

The effective polymerization process is very desirable in the field of macromolecule science. In this study, we present a facile synthetic method via aldol addition and condensation (AAC) that leads to the formation of fluorescent linear and branched polymers by cross coupling triphenylamines (TPA) and cyclohexanones (CYC) via CC bond formation. The methodology has the advantage of easy operations, mild reaction conditions, and high yield. Via the analysis of NMR, FT-IR, GPC, PL, UV, SEM, and theoretical calculation, the structure, physical properties, and optical behaviors of both polymers were well-characterized. The understanding of cell transplantation, migration, division, fusion, and lysis is a very challenging task. In this study, the linear polymer (LP) exhibits excellent biocompatibility and low cytotoxicity, which can be readily internalized by living cells in a noninvasive manner. The images of MPC5 cells indicate that LP can be a promising emissive fluorescence probe for bioimaging application.

研究领域: 高分子科学 · 生物学 · 医学
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Materials · 2016 ·Vol. 9 ·期 9 ·779 · IF 2.728

Multichromic Polymers Containing Alternating Bi(3-Methoxythiophene) and Triphenylamine Based Units with Para-Protective Substituents

Yingfei Hou,Lingqian Kong,Xiuping Ju,Xiaoli Liu,Jinsheng Zhao,Qingshan Niu

Two novel triphenylamine-based thiophene derivative monomers, 4-cyano-4′,4″-di(4-methoxythiophen-2-yl)triphenylamine and 4-methoxy-4′,4″-di(4-methoxythiophen-2-yl)triphenylamine, were successfully synthesized. The corresponding polymers including poly (4-cyano-4′,4″-di(4-methoxythiophen-2-yl)triphenylamine) and poly (4-methoxy-4′,4″-di(4-methoxythiophen-2-yl)triphenylamine) were electrochemically synthesized and characterized by multiple test method. The electrochemical measurements and spectroelectrochemical analyses revealed that both of the two polymers had quasi-reversible redox behavior and multi-electrochromic properties. The two polymer films showed reversible electrochemical oxidation, excellent optical contrasts in NIR region (62% at 1070 nm for the first polymer, and 86% at 1255 nm for the second polymer), satisfactory coloration efficiencies and fast switching times. The research on the application of the as prepared polymer in the fabrication of electrochromic device was also conducted, employing PCMTPA or PMMTPA as the anodically coloring materials.Keywords:4-cyanotriphenylamine;4-methoxytriphenylamine;bithiophenes derivatives;electrochromism;spectroelectrochemistry;electrochromic devices

研究领域: 材料科学 · 电化学 · 高分子化学 · 光电技术
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MATERIALS CHEMISTRY AND PHYSICS · 2021 · IF 4.094

Optoelectronic/memory storage properties of triphenylamine-based dual-function electrochromic materials

Lijing Chang,Yanjun Hou,Ju Bai,Haoran Xu,Yuhang Zhang,Shoulei Miao,Cheng Wang

Two electrochromic polymers containing triphenylamine groups with memory storage function were synthesized. The structures of the polymers have been characterized in detail. The polymers had good solubilities, excellent thermal stabilities and high fluorescence intensities. The reversible redox peak can also be clearly observed in the cyclic voltammogram, and the electrochromic color contrast was obvious. In addition, the polymers can also be used as memory storage materials with excellent "write-read-erase-rewrite" performance. Among them, the P2 film presented noticeable color changed from light yellow to pine green during the voltage 0 V–1.4 V, the coloring time was 3.3 s and the bleaching time was 3.7 s, the coloration efficiency was 207 cm 2  C −1 . The ON/OFF current ratio of P2 was 10 3.1 and the threshold voltage of P2 was 0.91 V. The results showed that these polymers have broad application prospects in the field of dual-function materials.

研究领域: 材料科学 · 光学
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Journal of Materials Chemistry B · 2016 ·Vol. 4 ·期 47 ·7549-7559 · IF 4.872

A novel triphenylamine-BODIPY dendron: click synthesis, near-infrared emission and a multi-channel chemodosimeter for Hg2+ and Fe3+

Bao-xing Shen,Ying Qian

A novel triphenylamine-BODIPY based Schiff base fluorescent probe (TPA-BODIPY-OH) with an emission in the near-infrared (NIR) region was designed and prepared by click reaction. TPA-BODIPY-OH showed three emission bands at 510 nm, 598 nm and 670 nm, and can detect Fe3+ and Hg2+ ions with remarkable fluorescence enhancement in THF/H2O (v/v, 1 : 1, buffered with 10 mM HEPES pH = 7.4) based on the hydrolysis reaction of the –CN bond, and naked eye detection was realized with an obvious color change. The stoichiometry between the probe and ions was deduced from a Job's plot, which is 1 : 3 for TPA-BODIPY-OH/Fe3+ and 1 : 2 for TPA-BODIPY-OH/Hg2+, respectively. The dissociation constant value was found to be 1.35 × 10−16 M for TPA-BODIPY-OH/Fe3+ and 2.06 × 10−11 M for TPA-BODIPY-OH/Hg2+. The low detection limit was calculated from the titration results with the values of 5.15 × 10−7 M for TPA-BODIPY-OH/Fe3+ and 6.81 × 10−7 M for TPA-BODIPY-OH/Hg2+, respectively. In order to investigate the biological applications of TPA-BODIPY-OH, a living cell imaging experiment was carried out. The results demonstrate that TPA-BODIPY-OH can be successfully applied as a bioimaging agent in living cells. In addition, amino-group-functionalized silica fluorescent nanoparticles (FNPs) encapsulating the TPA-BODIPY-OH dyes were prepared and characterized by transmission electron microscopy. TPA-BODIPY-OH/SiO2 nanoparticles exhibit good dispersibility, and the quantum yield of FNPs at 657 nm was 42.3%.

CAS / MDL: 577-11-7 78-08-0
研究领域: 化学 · 生物成像 · 材料科学
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RSC Advances · 2014 ·Vol. 5 ·期 9 ·6869-6878 · IF 3.708

A self-assembled triphenylamine-based fluorescent chemosensor for selective detection of Fe3+ and Cu2+ ions in aqueous solution

Li Wenfeng,Ma Hengchang,Lu con,Ma Yuan,Qi Chunxuan,Zhang Zhonwei,Yang Zengming,Cao Haiying,Lei ziqiang

A novel triphenylamine-based fluorescent sensor tris((4-amino)phenylduryl)amine (m-TAPA) for Fe3+/Cu2+ ion has been developed. m-TAPA shows high selectivity and sensitivity toward Fe3+/Cu2+ over alkali and transition metal ions in aqueous solution. The possible mechanism of fluorescence quenching was that Fe3+/Cu2+ can be captured by the NH2 groups of m-TAPA to form non-fluorescent complexes, resulting in strong quenching. The detection limits of Fe3+ and Cu2+ were calculated to be 230 nM and 620 nM, respectively. Furthermore, fluorescent test strips have been prepared for convenient detection of Fe3+ and Cu2+ ions in environmental water samples, even in drinking water.

研究领域: 分析化学 · 材料科学
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MICROCHIMICA ACTA · 2018 ·Vol. 185 ·期 2 ·1-10 · IF 5.705

A hyper-cross linked polymer as an adsorbent for the extraction of chlorophenols

Wang Yao,Ma Ruiyang,Xiao Ruobai,Hao Lin,Wu Qiuhua,Wang Chun,Wang Zhi

A porous material (polytriphenylamine; PTPA) was synthesized by using triphenylamine as the monomer and dimethoxymethane as the cross-linker. PTPA was characterized by Fourier infrared spectrometry, X-ray diffraction measurements, scanning electron microscopy and N 2 adsorption-desorption isotherms. The PTPA has a spherical-shape morphology and relatively high specific surface area. It is shown to be a viable adsorbent for solid phase extraction of 3-chlorophenol, 2,3-dichlorophenol, 2,4-dichlorophenol and 2,4.6-trichlorophenol prior to their determination by high performance liquid chromatography-mass spectrometry. Under the optimized conditions, recoveries from spiked samples are in the range from 92.5% to 106.3%. The limits of detection range from 0.03 to 0.3 ng mL −1 (at an S/N ratio of 3) in case of bottled juice, and from 0.03 to 0.1 ng g −1 in case of tomato samples. The enrichment factors for the four analytes are in the range of 127–183 for bottle juice, and from 110–150 for tomatos. Response is linear in the range of 1.0 to 40.0 ng mL −1 for juice, and 0.3–40.0 ng g −1 for tomatos. The relative standard deviations for the determination of the chlorophenols at 20 ng mL −1 in bottled beverage, and 20 ng g −1 in tomatos are lower than 5.7%. A polytriphenylamine polymer (PTPA) was prepared by using an external cross-linker method with triphenylamine as monomer and dimethoxymethane as cross-linker, and it was used as an adsorbent to extract chlorophenols from juice and vegetable samples.

研究领域: 环境科学 · 分析化学
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Scientific Reports · 2016 ·Vol. 6 ·期 1 ·1-9 · IF 5.228

A fast electrochromic polymer based on TEMPO substituted polytriphenylamine

Ji Lvlv,Dai Yuyu,Yan Shuanma,Lv Xiaojing,Su Chang,Xu Lihuan,Lv Yaokang,Ouyang Mi,Chen Zuofeng,Zhang Cheng

A novel strategy to obtain rapid electrochromic switching response by introducing 2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO) moiety into polytriphenylamine backbone has been developed. The electrochromic properties of the integrated polymer film are investigated and a possible mechanism is proposed with TEMPO as a counterion-reservoir group to rapidly balance the charges during electrochromic switching, which leads to significantly improved electrochromism performance.

CAS / MDL: 7646-69-7
研究领域: 材料科学 · 电化学
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DYES AND PIGMENTS · 2019 · IF 4.018

Synthesis of triphenylamine (TPA) dimers and applications in cell imaging

Yang Yuan,Pei Yin,Tao Wang,Zengming Yang,Weidong Yin,Shaoxiong Zhang,Chunxuan Qi,Ma Hengchang

A variety of triphenylamine (TPA) are shown to undergo C–C bond formation using quinone-based chloranil/H + reagent as the metal free oxidative system to afford triphenylamine dimers very conveniently. Then, TPA dimers have been further converted to the emission color tunable compounds via simple chemical transformations. Importantly, we established the primary relationship between chemical structures with the optical behaviors from the aspect of emission (λ em ) wavelength, fluorescence life time (τ) and aggregation-induced-emission (AIE) property in this work. The further application of these compounds to cell imaging was fully demonstrated.

研究领域: 有机化学 · 生物医学 · 材料科学
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FOOD CHEMISTRY · 2025 · IF 9.8

High-sensitivity detection of hydrogen sulfide and water content using a Triphenylamine-based fluorescent probe: Applications in food safety monitoring

Yanqing Xu,Zhaojiang Yin,Qian Long,Haotian Xie,Xinying Yan,Fusheng Liao,Hanfeng Cui,Hao Fan

This study reports the design and synthesis of a fluorescent probe TPA-ACL based on the triphenylamine (TPA) structure for the dual detection of hydrogen sulfide (H₂S) and water content. In the presence of H₂S, TPA-ACL exhibits a pronounced “turn-on” fluorescence response, demonstrating excellent selectivity and high sensitivity with a detection limit (LOD) of 2.02 nM. Furthermore, TPA-ACL enables real-time detection of H₂S using test strips, allowing for visual monitoring of H₂S gas generated during food spoilage, indicated by a color change from pale yellow to deep yellow. The probe was also successfully applied for the quantitative analysis of trace water content in food samples, with a detection limit (LOD) of 70.7 ppm (0.0071 vol%) in tetrahydrofuran (THF). This study provides a sensitive, efficient, and practical tool for detecting H 2 S and water content, demonstrating significant potential for applications in food safety monitoring.

CAS / MDL: 10025-87-3
研究领域: 分析化学 · 食品科学 · 环境监测
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TALANTA · 2023 · IF 6.1

A functional cobalt-organic framework constructed by triphenylamine tricarboxylate: Detect nitroaromatics by fluorescence sensing and UV-shielding

Peijiang Wang,Shanshan Jiang,Jun Zeng,Yuewen Huang,Bin Song,Bin Wang

Luminescent metal-organic frameworks (LMOF) with ligand-modified are a promising strategy to be applied to fabricate chemical sensors. Herein, a novel Co (II) metal-organic framework (Co-MOF), namely Co [(NTB) bpy] (NTB = 4,4′4″-tricarboxylic acid triphenylamine, bpy = 4,4 ′-bipyridyl), was successfully synthesized with excellent water stability and fluorescence properties. Due to the propeller structure of NTB ligands, a special topological structure of Co-MOF was shown: {2 4 .4 16 .6 8 }{2}4. It was proved that Co-MOF has great stability by soaking in different solvents for two weeks. Remarkably, the fluorescence quenching experiment verified that Co-MOF has excellent fluorescence sensor performance. Trinitrophenol, 2,4-dinitrophenol, and 2-amino-4-nitrotoluene (10 −5  M) with LOD of 9.00 × 10 −5 , 5.40 × 10 −5 and 5.07 × 10 −6  M can be detected via the process of fluorescence enhancement and quenching. Throughout the investigation, the mechanics of fluorescence quenching was performed. Due to the excellent UV absorption capacity of Co-MOF, it was a promising application to combine low-dimensional nanomaterials with sustainable biomass materials. A hybrid films of Co-MOF and cellulose acetate (CA) was generated. The hybrid films had highly transparency in the visible wavelength range and excellent UV-shielding ability owing to the CA/Co-MOF hybrid films enhanced the UV absorption capacity of Co-MOF.

研究领域: 材料科学 · 化学传感器 · 环境监测
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JOURNAL OF CHROMATOGRAPHY A · 2018 · IF 3.716

Use of a hypercrosslinked triphenylamine polymer as an efficient adsorbent for the enrichment of phenylurea herbicides

Xinyu Liang,Juntao Wang,Qiuhua Wu,Chun Wang,Zhi Wang

A hypercrosslinked triphenylamine polymer (HCTPA) was prepared through a simple one-step Friedel-Crafts alkylation reaction. The HCTPA had an extended π-conjugated system, large specific surface area and high micropore volume. In order to evaluate its extraction performance, the HCTPA was used as the adsorbent for the solid-phase extraction of the phenylurea herbicides (monuron, chlortoluron, isoproturon, monolinuron and buturon) from watermelon, tomato and cucumber samples. The main parameters that could affect the extraction efficiency including the sample volume, sample solution pH, sample solution loading rate and desorption conditions were investigated and optimized. Under the optimized conditions, the HCTPA showed a good extraction performance for the target analytes. The linear range for the quantification of the analytes was in the range of 0.4–160.0 ng g −1 with the correlation coefficients of 0.9996–0.9999. The limits of detection (S/N = 3) of the analytes by the method ranged from 0.06 to 0.12 ng g −1 for watermelon and tomato, and 0.06–0.15 ng g −1 for cucumber samples. The recoveries of the analytes for the method were between 83.1% and 112.5% with the relative standard deviations below 5.5%. These results indicate that the HCTPA can be used for the enrichment of phenylurea herbicides from complex matrix samples like watermelon, tomato and cucumbers.

研究领域: 分析化学 · 环境科学
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Chemistry-An Asian Journal · 2016 ·Vol. 11 ·期 18 ·2555-2563 · IF 4.592

Engineering the Interconnecting Position of Star-Shaped Donor–π–Acceptor Molecules Based on Triazine, Spirofluorene, and Triphenylamine Moieties for Color Tuning from Deep Blue to Green

Yafei Wang,Wanhui Liu,Jiyong Deng,Guohua Xie,Yuanwei Liao,Zuoming Qu,Hua Tan,Yu Liu,Weiguo Zhu

Pi-conjugated organic molecules featuring the donor–bridge–acceptor (D–π–A) structure have been widely used in semiconducting materials owing to their rigid structure, good thermal stability, excellent charge transfer, and high emission efficiency. To investigate the effect of the D–π–A molecular structure on the photophysical properties, in this contribution, three star-shaped D–π–A isomers based on the 2,4,6-triphenyl-1,3,5-triazine, spirofluorene, and triphenylamine moieties, that is, p -TFTPA, mp -TFTPA, and m -TFTPA, were synthesized by elaborately engineering the interconnecting position in the building-block units. The optophysical properties of these compounds were systematically explored by experiments and theory calculations. Definitively, changing the interconnecting position in these molecules played a significant role in the degree of π conjugation, which resulted in tunable emission colors from deep blue to green. Moreover, these isomers were employed as emissive dopants in organic light-emitting diodes. The highest external quantum efficiency of 2.3 % and current efficiency of 6.2 cd A −1 were achieved by using the p -TFTPA based device. This research demonstrates a feasible way to realize blue emitters by engineering D–π–A conjugation.

研究领域: 材料科学 · 光学
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