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Keywords = 2,4-diaminobenzoic acid

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21 pages, 10225 KB  
Article
Realization of Intermolecular Interactions as a Basis for Controlling Pervaporation Properties of Membranes Made of Aromatic Polyamide-Imides
by Svetlana V. Kononova, Galina N. Gubanova, Galina K. Lebedeva, Elena V. Kruchinina, Elena N. Vlasova, Elena N. Popova, Natalya V. Zakharova, Milana E. Vylegzhanina, Elena A. Novozhilova and Ksenia V. Danilova
Membranes 2025, 15(1), 23; https://doi.org/10.3390/membranes15010023 - 13 Jan 2025
Viewed by 1023
Abstract
New aromatic co-polyamide-imides (coPAIs) containing both carboxyl and hydroxyl groups in the repeating units were synthesized for the first time. Transport, thermal and morphological properties of dense nonporous membranes from PAIs obtained using the diacid chloride of 2-(4-carboxyphenyl)-1,3-dioxoisoindoline-5-carboxylic acid and diamines 5,5′-methylene-bis (2-aminophenol)) [...] Read more.
New aromatic co-polyamide-imides (coPAIs) containing both carboxyl and hydroxyl groups in the repeating units were synthesized for the first time. Transport, thermal and morphological properties of dense nonporous membranes from PAIs obtained using the diacid chloride of 2-(4-carboxyphenyl)-1,3-dioxoisoindoline-5-carboxylic acid and diamines 5,5′-methylene-bis (2-aminophenol)) and 3,5-Diaminobenzoic acid, taken in molar ratios of 7:3, 1:1, and 3:7, have been studied. High levels of membrane permeability accompanied by high selectivity for mixtures of liquids with significantly different polarities were determined by realization of intra- and intermolecular interactions in polymer, which was proved by thermal analyses and hydrodynamic characteristics of coPAIs. This effect is discussed in the context of the effectiveness of intermolecular interactions between polymer chains containing carboxyl and hydroxyl functional groups. Full article
(This article belongs to the Section Membrane Fabrication and Characterization)
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19 pages, 7793 KB  
Article
A Ratiometric Fluorescence Method Based on PCN-224-DABA for the Detection of Se(IV) and Fe(III)
by Mao-Ling Luo, Guo-Ying Chen, Wen-Jia Li, Jia-Xin Li, Tong-Qing Chai, Zheng-Ming Qian and Feng-Qing Yang
Biosensors 2024, 14(12), 626; https://doi.org/10.3390/bios14120626 - 19 Dec 2024
Cited by 1 | Viewed by 1416
Abstract
In this study, 3,4-diaminobenzoic acid (DABA) was introduced into the porphyrin metal–organic framework (PCN-224) for the first time to prepare a ratiometric fluorescent probe (PCN-224-DABA) to quantitatively detect ferric iron (Fe(III)) and selenium (IV) (Se(IV)). The fluorescence attributed to the DABA of PCN-224-DABA [...] Read more.
In this study, 3,4-diaminobenzoic acid (DABA) was introduced into the porphyrin metal–organic framework (PCN-224) for the first time to prepare a ratiometric fluorescent probe (PCN-224-DABA) to quantitatively detect ferric iron (Fe(III)) and selenium (IV) (Se(IV)). The fluorescence attributed to the DABA of PCN-224-DABA at 345 nm can be selectively quenched by Fe(III) and Se(IV), but the fluorescence emission peak attributed to tetrakis (4-carboxyphenyl) porphyrin (TCPP) at 475 nm will not be disturbed. Therefore, the ratio of I345nm/I475nm with an excitation wavelength of 270 nm can be designed to determine Fe(III) and Se(IV). After the experimental parameters were systematically optimized, the developed method shows good selectivity and interference resistance for Fe(III) and Se(IV) detection, and has good linearity in the ranges of 0.01–4 μM and 0.01–15 μM for Fe(III) and Se(IV) with a limit of detection of 0.045 μM and 0.804 μM, respectively. Furthermore, the quenching pattern was investigated through the Stern–Volmer equation, and the results suggest that both Se(IV) and Fe(III) quenched on PCN-224-DABA can be attributed to the dynamic quenching. Finally, the constructed ratiometric fluorescent probe was applied in the spiked detection of lake water samples, which shows good applicability in real sample analysis. Moreover, the Fe(III) and Se(IV) contents in spinach and selenium-enriched rice were determined, respectively. Full article
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18 pages, 3870 KB  
Article
Carbon–Carbon Composite Membranes Derived from Small-Molecule-Compatibilized Immiscible PBI/6FDA-DAM-DABA Polymer Blends
by Chamaal Karunaweera, Nimanka P. Panapitiya, Samitha Panangala, Edson V. Perez, Inga H. Musselman, Kenneth J. Balkus and John P. Ferraris
Separations 2024, 11(4), 108; https://doi.org/10.3390/separations11040108 - 1 Apr 2024
Cited by 1 | Viewed by 2117
Abstract
The use of immiscible polymer blends in gas separations is limited due to uncontrollable phase separation. In contrast, compatibilized immiscible polymer blends can be used as precursors with controlled morphologies that allow for a unique pore architecture. Herein, an immiscible polymer blend (1:1) [...] Read more.
The use of immiscible polymer blends in gas separations is limited due to uncontrollable phase separation. In contrast, compatibilized immiscible polymer blends can be used as precursors with controlled morphologies that allow for a unique pore architecture. Herein, an immiscible polymer blend (1:1) comprising polybenzimidazole (PBI) and the copolyimide 6FDA-DAM:DABA [3:2], derived from reacting 4,4-(hexafluoroisopropylidene)diphthalic anhydride (6FDA) with 2,4,6-trimethyl-1,3-phenylenediamine (DAM) and 3,5-diaminobenzoic acid (DABA), were combined with durene diamine as a compatibilizer. The compatibilizer helped reduce the 6FDD domain sizes from 5.6 µm down to 0.77 µm and induced a more even 6FDA distribution and the formation of continuous thin-selective PBI layers. The carbon–carbon composite membranes derived from the compatibilized immiscible polymer blends showed a 3-fold increase in both H2 permeability and H2/CO2 selectivity compared to the membranes derived from non-compatibilized polymer blends. The H2 permeability of the compatibilized immiscible polymer blends increased from 3.6 to 27 Barrer, and their H2/CO2 selectivity increased from 7.2 to 20. The graphitic domain size of the carbon–carbon composite membranes derived from the polymer blends also increased from 6.3 nm for the non-compatibilized blend to 10.0 nm for the compatibilized blend. Full article
(This article belongs to the Section Materials in Separation Science)
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17 pages, 4246 KB  
Article
Tailoring the Micropore Structure of 6FDA-Based Network Polyimide Membranes for Advanced Gas Separation by Decarboxylation
by Yuxuan Zhao, Hongyan Wang, Xiangyun Liu, Xueping Zong, Jiangzhou Luo and Song Xue
Membranes 2023, 13(5), 461; https://doi.org/10.3390/membranes13050461 - 24 Apr 2023
Cited by 4 | Viewed by 2228
Abstract
The 6FDA-based network PI has attracted significant attention for gas separation. A facile strategy to tailor the micropore structure within the network PI membrane prepared by the in situ crosslinking method is extremely significant for achieving an advanced gas separation performance. In this [...] Read more.
The 6FDA-based network PI has attracted significant attention for gas separation. A facile strategy to tailor the micropore structure within the network PI membrane prepared by the in situ crosslinking method is extremely significant for achieving an advanced gas separation performance. In this work, the 4,4′-diamino-2,2′-biphenyldicarboxylic acid (DCB) or 3,5-diaminobenzoic acid (DABA) comonomer was incorporated into the 6FDA-TAPA network polyimide (PI) precursor via copolymerization. The molar content and the type of carboxylic-functionalized diamine were varied in order to easily tune the resulting network PI precursor structure. Then, these network PIs containing carboxyl groups underwent further decarboxylation crosslinking during the following heat treatment. Properties involving thermal stabilities, solubility, d-spacing, microporosity, and mechanical properties were investigated. Due to the decarboxylation crosslinking, the d-spacing and the BET surface areas of the thermally treated membranes were increased. Moreover, the content of DCB (or DABA) played a key role in determining the overall gas separation performance of the thermally treated membranes. For instance, after the heating treatment at 450 °C, 6FDA-DCB:TAPA (3:2) showed a large increment of about ~532% for CO2 gas permeability (~266.6 Barrer) coupled with a decent CO2/N2 selectivity~23.6. This study demonstrates that incorporating the carboxyl-containing functional unit into the PI backbone to induce decarboxylation offers a practical approach with which to tailor the micropore structure and corresponding gas transport properties of 6FDA-based network PIs prepared by the in situ crosslinking method. Full article
(This article belongs to the Special Issue Advances in Polymeric Membranes for Carbon Capture and Storage (CCS))
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18 pages, 5192 KB  
Article
Synthesis, Characterization, Thermal Analysis, DFT, and Cytotoxicity of Palladium Complexes with Nitrogen-Donor Ligands
by Sattar R. Majeed, Mina A. Amin, Fawzy A. Attaby, Marta E. Alberto and Ahmed A. Soliman
Molecules 2022, 27(3), 964; https://doi.org/10.3390/molecules27030964 - 31 Jan 2022
Cited by 7 | Viewed by 3479
Abstract
Three new palladium complexes ([Pd(DABA)Cl2], [Pd(CPDA)Cl2], and [Pd(HZPY)Cl2]) bearing dinitrogen ligands (DABA: 3,4-diaminobenzoic acid; CPDA: 4-chloro–o-phenylenediamine; HZPY: 2-hydraziniopyridine) were synthesized, characterized, and tested against breast cancer (MCF-7), prostate carcinoma cell line (PC3) and liver carcinoma cell line [...] Read more.
Three new palladium complexes ([Pd(DABA)Cl2], [Pd(CPDA)Cl2], and [Pd(HZPY)Cl2]) bearing dinitrogen ligands (DABA: 3,4-diaminobenzoic acid; CPDA: 4-chloro–o-phenylenediamine; HZPY: 2-hydraziniopyridine) were synthesized, characterized, and tested against breast cancer (MCF-7), prostate carcinoma cell line (PC3) and liver carcinoma cell line (HEPG2). [Pd(DABA)Cl2] complex exhibited the highest inhibition percentage, lying between 68–71%. The hydrolysis mechanism of each palladium complex, the key step preceding the binding to the biological target, as well as their photophysical properties were explored by means of DFT and TDDFT computations. Results indicate a faster hydrolysis process for the Pd(DABA)Cl2 complex. The computed activation energies for the first and second hydrolysis processes suggest that all the compounds could reach DNA in their monohydrated form. Full article
(This article belongs to the Special Issue Density Functional Theory in the Age of Chemical Intelligence)
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12 pages, 22522 KB  
Article
Constructing Polyimide Aerogels with Carboxyl for CO2 Adsorption
by Yangfeng Gao, Chao Dong, Fan Zhang, Hongwei Ma and Yang Li
Polymers 2022, 14(3), 359; https://doi.org/10.3390/polym14030359 - 18 Jan 2022
Cited by 17 | Viewed by 3257
Abstract
In this study, mesoporous polyimide aerogels with carboxyl were successfully synthesized by the co-polymerization method at room temperature from pyromellitic dianhydride and 1,3,5-triaminophenoxybenzene, 3,5-diaminobenzoic acid, and 2,2′-dimethyl-4,4′-diaminobiphenyl. Compared to previously reported porous organic polymer materials, this aerogel has the advantage of a simple [...] Read more.
In this study, mesoporous polyimide aerogels with carboxyl were successfully synthesized by the co-polymerization method at room temperature from pyromellitic dianhydride and 1,3,5-triaminophenoxybenzene, 3,5-diaminobenzoic acid, and 2,2′-dimethyl-4,4′-diaminobiphenyl. Compared to previously reported porous organic polymer materials, this aerogel has the advantage of a simple and efficient synthesis method. The thermal decomposition temperatures of the obtained polyimide aerogels are all above 400 °C and have excellent thermal stability. Among them, the largest specific surface area is 62.03 m2/g. Although the surface area of this aerogel is not large enough, it has considerable CO2 adsorption properties. The adsorption capacity of CO2 is up to 11.9 cm3/g, which is comparable to those of previously reported porous materials. The high CO2 adsorption is attributed to the abundance of carboxyl groups in the polyimide networks. The mild and convenient synthesis method and high CO2 adsorption capacity indicate that the polyimide aerogel with carboxyl is suitable as a good candidate material for CO2 adsorption. Full article
(This article belongs to the Special Issue Advances of Aerogels and Their Polymer Composites)
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18 pages, 5719 KB  
Article
Removal of Ibuprofen from Water by Different Types Membranes
by Mahdi Bourassi, Magda Kárászová, Mariia Pasichnyk, Raul Zazpe, Jana Herciková, Vlastimil Fíla, Jan M. Macak and Jana Gaálová
Polymers 2021, 13(23), 4082; https://doi.org/10.3390/polym13234082 - 24 Nov 2021
Cited by 12 | Viewed by 3392
Abstract
Ibuprofen separation from water by adsorption and pertraction processes has been studied, comparing 16 different membranes. Tailor-made membranes based on Matrimid, Ultem, and diaminobenzene/diaminobenzoic acid with various contents of zeolite and graphene oxide, have been compared to the commercial polystyrene, polypropylene, and polydimethylsiloxane [...] Read more.
Ibuprofen separation from water by adsorption and pertraction processes has been studied, comparing 16 different membranes. Tailor-made membranes based on Matrimid, Ultem, and diaminobenzene/diaminobenzoic acid with various contents of zeolite and graphene oxide, have been compared to the commercial polystyrene, polypropylene, and polydimethylsiloxane polymeric membranes. Experimental results revealed lower ibuprofen adsorption onto commercial membranes than onto tailor-made membranes (10–15% compared to 50–70%). However, the mechanical stability of commercial membranes allowed the pertraction process application, which displayed a superior quantity of ibuprofen eliminated. Additionally, the saturation of the best-performing commercial membrane, polydimethylsiloxane, was notably prevented by atomic layer deposition of (3-aminopropyl)triethoxysilane. Full article
(This article belongs to the Special Issue Advanced Polymeric Membranes Suitable for Water Treatment)
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12 pages, 2718 KB  
Article
Eco-Friendly Water-Processable Polyimide Binders with High Adhesion to Silicon Anodes for Lithium-Ion Batteries
by Yujin So, Hyeon-Su Bae, Yi Young Kang, Ji Yun Chung, No Kyun Park, Jinsoo Kim, Hee-Tae Jung, Jong Chan Won, Myung-Hyun Ryou and Yun Ho Kim
Nanomaterials 2021, 11(12), 3164; https://doi.org/10.3390/nano11123164 - 23 Nov 2021
Cited by 26 | Viewed by 6094
Abstract
Silicon is an attractive anode material for lithium-ion batteries (LIBs) because of its natural abundance and excellent theoretical energy density. However, Si-based electrodes are difficult to commercialize because of their significant volume changes during lithiation that can result in mechanical damage. To overcome [...] Read more.
Silicon is an attractive anode material for lithium-ion batteries (LIBs) because of its natural abundance and excellent theoretical energy density. However, Si-based electrodes are difficult to commercialize because of their significant volume changes during lithiation that can result in mechanical damage. To overcome this limitation, we synthesized an eco-friendly water-soluble polyimide (W-PI) precursor, poly(amic acid) salt (W-PAmAS), as a binder for Si anodes via a simple one-step process using water as a solvent. Using the W-PAmAS binder, a composite Si electrode was achieved by low-temperature processing at 150 °C. The adhesion between the electrode components was further enhanced by introducing 3,5-diaminobenzoic acid, which contains free carboxylic acid (–COOH) groups in the W-PAmAS backbone. The –COOH of the W-PI binder chemically interacts with the surface of Si nanoparticles (SiNPs) by forming ester bonds, which efficiently bond the SiNPs, even during severe volume changes. The Si anode with W-PI binder showed improved electrochemical performance with a high capacity of 2061 mAh g−1 and excellent cyclability of 1883 mAh g−1 after 200 cycles at 1200 mA g−1. Therefore, W-PI can be used as a highly effective polymeric binder in Si-based high-capacity LIBs. Full article
(This article belongs to the Special Issue Emerging Nanomaterials for Lithium-Sulfur Batteries and Beyond II)
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14 pages, 3000 KB  
Article
Potentiometric Electronic Tongue for Pharmaceutical Analytics: Determination of Ascorbic Acid Based on Electropolymerized Films
by Gabriela Broncová, Vadim Prokopec and Tatiana V. Shishkanova
Chemosensors 2021, 9(5), 110; https://doi.org/10.3390/chemosensors9050110 - 14 May 2021
Cited by 8 | Viewed by 3336
Abstract
This work deals with the design of an experimental potentiometric electronic tongue (ET) for the recognition of various samples of effervescent tablets with different ascorbic acid (vitamin C) contents. The ET consisted of twelve potentiometric sensors based on conductive polymers, which were derived [...] Read more.
This work deals with the design of an experimental potentiometric electronic tongue (ET) for the recognition of various samples of effervescent tablets with different ascorbic acid (vitamin C) contents. The ET consisted of twelve potentiometric sensors based on conductive polymers, which were derived from 4-amino-2,1,3-benzothiadiazole, 3,4-diaminobenzoic acid, and neutral red on the surface of the platinum electrode using cyclic voltammetry. The aim of the potentiometric study was to assess the influence of the vitamin C content and the composition of the matrix of commercial samples on the potentiometric response. The results obtained from the sensor array proved that the stability of the potentiometric signal and the accuracy of measurements are affected by individual sensors. The identification of the vitamin C content in the individual samples of effervescent tablets obtained by means of the potentiometric electronic tongue corresponded with the results of the coulometric titration. Full article
(This article belongs to the Special Issue Functionalized Materials for Chemosensor Applications)
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9 pages, 1495 KB  
Article
Fluorescence Sensing of Caffeine in Tea Beverages with 3,5-diaminobenzoic Acid
by Chenxu Du, Chaoqun Ma, Jiao Gu, Lei Li and Guoqing Chen
Sensors 2020, 20(3), 819; https://doi.org/10.3390/s20030819 - 3 Feb 2020
Cited by 20 | Viewed by 6131
Abstract
A rapid, selective and sensitive method for the detection of caffeine in tea infusion and tea beverages are proposed by using 3,5-diaminobenzoic acid as a fluorescent probe. The 3,5-diaminobenzoic acid emits strong fluorescence around 410 nm under the excitation of light at 280 [...] Read more.
A rapid, selective and sensitive method for the detection of caffeine in tea infusion and tea beverages are proposed by using 3,5-diaminobenzoic acid as a fluorescent probe. The 3,5-diaminobenzoic acid emits strong fluorescence around 410 nm under the excitation of light at 280 nm. Both the molecular electrostatic potential analysis and fluorescent lifetime measurement proved that the existence of caffeine can quench the fluorescence of 3,5-diaminobenzoic acid. Under the optimal experimental parameters, the 3,5-diaminobenzoic acid was used as a fluorescent probe to detect the caffeine aqueous solution. There exists a good linear relationship between the fluorescence quenching of the fluorescent probe and the concentration of caffeine in the range of 0.1–100 μM, with recovery within 96.0 to 106.2%, while the limit of detection of caffeine is 0.03 μM. This method shows a high selectivity for caffeine. The caffeine content in different tea infusions and tea beverages has been determined and compared with the results from HPLC measurement. Full article
(This article belongs to the Special Issue Fluorescence-Based Sensors)
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10 pages, 2888 KB  
Article
Highly Fluorescent Green Carbon Dots as a Fluorescent Probe for Detecting Mineral Water pH
by Tingyu Wang, Guoqing Chen, Lei Li and Yamin Wu
Sensors 2019, 19(17), 3801; https://doi.org/10.3390/s19173801 - 3 Sep 2019
Cited by 46 | Viewed by 5587
Abstract
In this report, high-brightness green carbon dots were successfully prepared using 3,5-diaminobenzoic acid as the sole precursor and synthesized in one step using a solvothermal strategy. Under the excitation of 365 nm ultraviolet light, the quantum yield of carbon dots is as high [...] Read more.
In this report, high-brightness green carbon dots were successfully prepared using 3,5-diaminobenzoic acid as the sole precursor and synthesized in one step using a solvothermal strategy. Under the excitation of 365 nm ultraviolet light, the quantum yield of carbon dots is as high as 53.8%. Experiments revealed that the carbon dots are highly carbonized and the surface is rich in amino and carboxyl groups. The synthesized carbon dots have good water solubility, and are resistant to ions and temperature. The fluorescence intensity of CDs is sensitive to pH changes and is linearly correlated with the pH in the near-neutral range (pH = 6.0 to 9.0). Our experiments showed that carbon dots were sensitive and accurate fluorescent probes for measuring the pH value of drinking water, which could provide an effective method for measuring the pH value of water in the future. Full article
(This article belongs to the Section Chemical Sensors)
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10 pages, 911 KB  
Article
Preparation and Characterization of Transparent Polyimide–Silica Composite Films Using Polyimide with Carboxylic Acid Groups
by Kwan Ho Moon, Boknam Chae, Ki Seung Kim, Seung Woo Lee and Young Mee Jung
Polymers 2019, 11(3), 489; https://doi.org/10.3390/polym11030489 - 13 Mar 2019
Cited by 25 | Viewed by 6845
Abstract
Polyimide (PI) composite films with thicknesses of approximately 100 µm were prepared via a sol–gel reaction of 3-aminopropyltrimethoxysilane (APTMS) with poly(amic acid) (PAA) composite solutions using a thermal imidization process. PAA was synthesized by a conventional condensation reaction of two diamines, 3,5-diaminobenzoic acid [...] Read more.
Polyimide (PI) composite films with thicknesses of approximately 100 µm were prepared via a sol–gel reaction of 3-aminopropyltrimethoxysilane (APTMS) with poly(amic acid) (PAA) composite solutions using a thermal imidization process. PAA was synthesized by a conventional condensation reaction of two diamines, 3,5-diaminobenzoic acid (DABA), which has a carboxylic acid side group, and 2,2′-bis(trifluoromethyl)benzidine (TFMB), with 4,4′-(hexafluoroisopropylidene)diphthalic anhydride (6FDA) in N,N-dimethylacetamide (DMAc). The PAA–silica composite solutions were prepared by mixing PAA with carboxylic acid side groups and various amounts of APTMS in a sol–gel process in DMAc using hydrochloric acid as a catalyst. The obtained PI–silica composite films showed relatively good thermal stability, and the thermal stability increased with increasing APTMS content. The optical properties and in-plane coefficient of thermal expansion (CTE) values of the PI–silica composite films were investigated. The CTE of the PI–silica composite films changed from 52.0 to 42.1 ppm/°C as the initial content of APTMS varied. The haze values and yellowness indices of the composite films increased as a function of the APTMS content. Full article
(This article belongs to the Special Issue Advanced Engineering Plastics)
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6 pages, 34 KB  
Article
Carotamine, a Unique Aromatic Amide from Daucus Carota L. Var Biossieri (Apiaceae)
by Omayma A. Eldahshan, Nahla A. Ayoub, Abd-El Naser B. Singab and Mohamed M. El-Azizi
Molecules 2002, 7(6), 501-506; https://doi.org/10.3390/70600501 - 30 Jun 2002
Cited by 2 | Viewed by 9383
Abstract
The unique aromatic peptide 4-(p-aminobenzoylamino)-2-aminobenzoic acid, carotamine, together with 2,4-diaminobenzoic acid, isolated for the first time from a plant source, were identified from the aqueous alcoholic extract of the aerial parts of Daucus carota L. var. boissieri (Apiaceae). The structures were determined through [...] Read more.
The unique aromatic peptide 4-(p-aminobenzoylamino)-2-aminobenzoic acid, carotamine, together with 2,4-diaminobenzoic acid, isolated for the first time from a plant source, were identified from the aqueous alcoholic extract of the aerial parts of Daucus carota L. var. boissieri (Apiaceae). The structures were determined through conventional methods of analysis and confirmed by LC-ESI/MS and NMR spectral analysis. Full article
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