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RSC Advances · 2017 ·Vol. 7 ·期 65 ·40996-41003 · IF 3.108

High performance polyimides with good solubility and optical transparency formed by the introduction of alkyl and naphthalene groups into diamine monomers

Tianyun Li,Huahua Huang,Lei Wang,Yongming Chen

Three kinds of naphthalene-containing diamines with –H, –CH3 or –CH(CH3)2 substituents at the ortho-positions of the aniline ring including 4,4′-(naphthalen-1-ylmethylene)dianiline (BAN-1), 4,4′-(naphthalen-1-ylmethylene)bis(2,6-dimethylaniline) (BAN-2) and 4,4′-(naphthalen-1-ylmethylene)bis(2,6-diisopropylaniline) (BAN-3) were synthesized via a simple one-step electrophilic substitution reaction. These diamines were then reacted with three commercial dianhydrides, via chemical imidization under microwave irradiation, to obtain nine types of polyimide (PI). It was found that the introduction of alkyl side groups can improve the solubility and optical transparency of PIs. Moreover, compared with BAN-2 based PIs containing –CH3 groups, BAN-3 based PIs containing –CH(CH3)2 groups exhibited better solubility and optical transparency (transmittances at 450 nm of over 86%). Meanwhile, due to the presence of the rigid naphthalene side groups, all the PIs possessed high thermal stability with a glass transition temperature (Tg) of over 290 °C and a decomposition temperature at 5% weight loss of over 510 °C under nitrogen. Furthermore, the Tg of PI-2B composed of BAN-2 and 3,3′,4,4′-biphenyltetracarboxylic dianhydride (BPDA) was found to be as high as 387 °C, which is comparable to that of the commercial and conventional PI material (Kapton®, Tg = 390 °C).

研究领域: 材料科学 · 化学工程
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POLYMER BULLETIN · 2011 ·Vol. 67 ·期 9 ·1761-1771 · IF 1.215

Poly(ether ketone azomethane)s and poly(ether ketone imide)s containing naphthylene moieties

Zhu Ming,Liu Xiao,Liu Baijun,Jiang Zhenhuan,Matsumoto Toshihiko

A new diamine monomer, 1,5-bis[4-(4-aminophenoxy)]benzoyl-2,6-dimethoxynaphthalene, was synthesized via a Friedel–Crafts acylation reaction followed by an aromatic nucleophilic substitution reaction. Six ether–ketone linked polymers, named as poly(ether ketone azomethane)s and poly(ether ketone imide)s, were successfully prepared through the polycondensations of the diamine monomer with dialdehydes and dianhydrides, respectively. These naphthylated polymers exhibited high T g values (142–288 °C), due to their bulky and rigid chemical structure. Meanwhile, they showed good thermal stability and improved solubility. Typically, some of them were casted into thin flexible film and showed high moduli.

研究领域: 材料科学 · 高分子化学
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ORGANIC ELECTRONICS · 2019 · IF 3.495

Functional gate-dielectrics containing naphthyl for organic thin film transistors

Jiawei Zou,Ting Xu,Jiufu Zhu,Zuosen Shi,Wei Wang,Zhanchen Cui

Here, we copolymerize a monomer containing naphthyl group with 2-hydroxyethyl methacrylate (HEMA) and glycidyl methacrylate (GlyMA) in various molar ratio to obtain copolymers as functional gate dielectric layers of thin-film transistors (TFTs). Using naphthyl-containing molecule to have similar chemical structure with pentance to adjust the grain size of semiconductor. The results indicated that the semiconductor grains size decreased as molar percentage of naphthyl-containing compound in the polymer structure increased, which could also affect the charge carrier mobility of the pentacene thin-film transistors (TFTs). Therefore, this can be a promising manner to fabricate pentacene TFTs with a high charge carrier mobility by using functionalized dielectric layers to obtain uniform grain size of the pentacene semiconductor.

CAS / MDL: 106-91-2 868-77-9
研究领域: 材料科学 · 有机电子学
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JOURNAL OF MOLECULAR LIQUIDS · 2021 · IF 6.165

Novel asymmetrical bis-surfactants with naphthalene and two amide groups: Synthesis, foamability and foam stability

Yue Jia,Xiangfeng Guo,Lihua Jia,Zhenlong Zhao,Rui Yang,Yu Zhang,Hong Sun

A series of novel asymmetrical bis-surfactants (C n NCS, n  = 10, 12, 14, 16), comprising a naphthalene group and a long chain hydrocarbon (as hydrophobic moieties), a quaternary ammonium group, one ether group and double amides (as hydrophilic moieties), and ethylidene as linkage groups, were designed, prepared, and characterized through proton and carbon nuclear magnetic resonance, Fourier-transform infrared, and electrospray ionization mass spectrometry analyses. The surface activity was studied by surface tension measurements. C n NCS exhibited low critical micelle concentrations (0.708–0.004 mmol L −1 ) and excellent surface tension reducing abilities. Moreover, the introduction of naphthyl and amido groups into C 12 NCS significantly enhanced the foamability and foam stability. This is attributed mainly to cooperative noncovalent interactions such as hydrophobic interactions of the long chain hydrocarbons, π-π stacking of the naphthyl groups , hydrogen-bonding of the amido groups of C 12 NCS itself and hydrogen bonding of C 12 NCS with water, and electrostatic interaction, which induced a decrease in the surface tension, leading to a compact and dense arrangement of the C 12 NCS molecules at the air–water interface to form a tight film. Both features enabled foam formation, slowed liquid drainage from the foam, and prevented the gas from diffusing through the monolayer, thus enhancing the foam stability. In addition, the long-acting emulsifying ability of C 12 NCS and good antibacterial activity of C n NCS were also demonstrated. Moreover, hydrogen-bonding of the amido groups and π-π stacking of the naphthyl groups of C n NCS were verified from the 1 H NMR and fluorescence spectra , respectively. This work provides a feasible strategy for the synthesis of highly efficient foaming, emulsifying, and bacteriostatic agents.

研究领域: 化学 · 材料科学 · 界面科学
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POLYMER BULLETIN · 2016 ·Vol. 74 ·期 8 ·3109-3121 · IF 1.371

Photoisomerization of waterborne polyurethane with side-chained phenylazonaphthalene group

Sun Wei,Zheng Yan,Zhang Xingyuan

Novel waterborne polyurethane (WPU) with side-chained Phenylazonaphthalene group was prepared by step-growth addition polymerization between isophorone diisocyanate (IPDI), polytetramethylene ether glycol (PTMG), 2, 2-dimethylol propionic acid (DMPA) and a self-made azo diol, N , N -(2-hydroxyethyl)-4-phenylazo naphthylamine (HPN), as a chain extender to partially substitute for 1, 4-butanediol (BDO). 1 H nuclear magnetic resonance spectra ( 1 H NMR), Fourier transform infrared spectroscopy (FTIR) and Ultraviolet–Visible (UV–Vis) spectroscopy were used to research the properties of HPN and HPN-WPU. The WPU latex presented obvious trans–cis photoisomerization during UV radiation and the absorption wavelength of the HPN exhibited a blue shift after attached into polyurethane chains. It needed longer irradiated time to finish isomerization due to the emulsion aggregated states, comparing with phenylazonaphthalene monomer solution and WPU dilute solution.

研究领域: 材料科学 · 高分子化学
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MICROPOROUS AND MESOPOROUS MATERIALS · 2020 · IF 4.551

Facile synthesis of dual-functionalized microporous organic network for efficient removal of cationic dyes from water

Xue Li,Yuan-Yuan Cui,Ying-Jun Chen,Cheng-Xiong Yang,Xiu-Ping Yan

A facile one-step anhydride hydrolysis strategy was rationally designed to synthesize a novel dual-functionalized microporous organic network (MON-4COOH) with enriched naphthalene and carboxyl groups for efficient removal of cationic dyes. The pre-designed electrostatic, hydrogen bonding , π-π and hydrophobic interaction sites on MON-4COOH led to the complete removal of three typical cationic dyes methylene blue, malachite green and crystal violet (25 mg L −1 for each) within 20 s and gave their maximum adsorption capacities of 2564, 3126 and 1114 mg g −1 , respectively. The adsorption of these cationic dyes fitted well with pseudo-second-order kinetic and Langmuir adsorption models. The adsorption kinetics and capacities of these cationic dyes on MON-4COOH were much faster and higher than many other reported adsorbents. The negatively charged MON-4COOH also gave much faster adsorption kinetic and larger adsorption capacity for cationic (methylene blue, malachite green and crystal violet) dyes than anionic dye. The excellent flow-through water treatment ability and reusability also made MON-4COOH highly potential for the remediation of cationic dyes polluted water. This work provided a feasible way to design and synthesize dual-functionalized MONs for efficient adsorption and elimination of environmental pollutants from water.

CAS / MDL: 7681-65-4
研究领域: 环境科学 · 材料科学
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