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Keywords = alkoxy side chain

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22 pages, 10544 KiB  
Article
Diamine Crosslinked Addition-Type Diblock Poly(Norbornene)s-Based Anion Exchange Membranes with High Conductivity and Stability for Fuel Cell Applications
by Quan Li, Xiaohui He, Ling Feng, Jia Ye, Wenjun Zhang, Longming Huang and Defu Chen
Polymers 2024, 16(24), 3534; https://doi.org/10.3390/polym16243534 - 18 Dec 2024
Cited by 2 | Viewed by 1342
Abstract
Anion exchange membranes (AEMs) as a kind of important functional material are widely used in fuel cells. However, synthetic AEMs generally suffer from low conductivity, poor alkaline stability, and poor dimensional stability. Constructing efficient ion transport channels is widely regarded as one of [...] Read more.
Anion exchange membranes (AEMs) as a kind of important functional material are widely used in fuel cells. However, synthetic AEMs generally suffer from low conductivity, poor alkaline stability, and poor dimensional stability. Constructing efficient ion transport channels is widely regarded as one of the most effective strategies for developing AEMs with high conductivity and low swelling ratio. Herein we demonstrate a versatile strategy to prepare the AEMs with both high conductivity and excellent alkali stability via all-carbon hydrogen block copolymer backbone hydrophilic crosslinking and introducing flexible alkoxy spacer chains. Additionally, we investigated the impact of the crosslinking degree on the AEMs’ performances. It was found that the dosage of the hydrophilic crosslinker has a significant impact on the construction of efficient ion transport channels in the AEMs. Amazingly, the CL30-aPNB-TMHDA-TMA exhibited the highest hydroxide conductivity (138.84 mS cm−1), reasonable water uptake (54.96%), and a low swelling ratio (14.07%) at 80 °C. Meanwhile, the membrane showed an excellent alkaline stability in a 1 M NaOH solution at 80 °C for 1008 h (ion exchange capacity (IEC) and OH conductivity remained at 91.9% and 89.12%, respectively). The single cells assembled with CL30-aPNB-TMHDA-TMA exhibited a peak power density of 266.2 mW cm−2 under a current density of 608 mA cm−2 at 80 °C. The novel developed composite strategy of flexible alkoxy side chains with hydrophilic crosslinking modification is potentially promised to be an effective approach to develop the high-performance AEMs. Full article
(This article belongs to the Special Issue Polymeric Membrane Science and Surface Modification Technologies)
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13 pages, 4110 KiB  
Article
The Influence of Molecular Weights on Dispersion and Thermoelectric Performance of Alkoxy Side-Chain Polythiophene/Carbon Nanotube Composite Materials
by Xiaogang Chen, Shihong Chen, Dagang Wang, Yongfu Qiu, Zhongming Chen, Haixin Yang, Qing Yang, Zijian Yin and Chengjun Pan
Polymers 2024, 16(17), 2444; https://doi.org/10.3390/polym16172444 - 29 Aug 2024
Cited by 1 | Viewed by 1276
Abstract
In the development of wearable electronic devices, the composite modification of conductive polymers and single-walled carbon nanotubes (SWCNTs) has become a burgeoning research area. This study presents the synthesis of a novel polythiophene derivative, poly(3-alkoxythiophene) (P3(TEG)T), with alkoxy side chains. Different molecular weight [...] Read more.
In the development of wearable electronic devices, the composite modification of conductive polymers and single-walled carbon nanotubes (SWCNTs) has become a burgeoning research area. This study presents the synthesis of a novel polythiophene derivative, poly(3-alkoxythiophene) (P3(TEG)T), with alkoxy side chains. Different molecular weight variants of P3(TEG)T (P1–P4) were prepared and combined with SWCNTs to form composite materials. Density functional theory (DFT) calculations revealed a reduced bandgap for P3(TEG)T. Raman spectroscopy demonstrated π-π interactions between P3(TEG)T and SWCNTs, facilitating the dispersion of single-walled carbon nanotubes and the formation of a continuous conductive network. Among the composite films, P4/SWCNTs-0.9 exhibited the highest thermoelectric performance, with a power factor (PF) value of 449.50 μW m−1 K−2. The fabricated flexible thermoelectric device achieved an output power of 3976.92 nW at 50 K, with a tensile strength of 59.34 MPa for P4/SWCNTs. Our findings highlight the strong interfacial interactions between P3(TEG)T and SWCNTs in the composite material, providing an effective charge transfer pathway. Furthermore, an improvement in the tensile performance was observed with an increase in the molecular weight of the polymer used in the composite, offering a viable platform for the development of high-performance flexible organic thermoelectric materials. Full article
(This article belongs to the Section Biobased and Biodegradable Polymers)
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11 pages, 3235 KiB  
Article
The Enhanced Thermoelectric and Mechanical Performance of Polythiophene/Single-Walled Carbon Nanotube Composites with Polar Ethylene Glycol Branched-Chain Modifications
by Qing Yang, Shihong Chen, Dagang Wang, Yongfu Qiu, Zhongming Chen, Haixin Yang, Xiaogang Chen, Zijian Yin and Chengjun Pan
Polymers 2024, 16(7), 943; https://doi.org/10.3390/polym16070943 - 29 Mar 2024
Cited by 3 | Viewed by 1659
Abstract
In order to develop flexible thermoelectric materials with thermoelectric and mechanical properties, in this study, we designed and synthesized polythiophene derivatives with branched ethylene glycol polar side-chains named P3MBTEMT, which were used in combination with single-walled carbon nanotubes (SWCNTs) to prepare composite thin [...] Read more.
In order to develop flexible thermoelectric materials with thermoelectric and mechanical properties, in this study, we designed and synthesized polythiophene derivatives with branched ethylene glycol polar side-chains named P3MBTEMT, which were used in combination with single-walled carbon nanotubes (SWCNTs) to prepare composite thin films and flexible thermoelectric devices. A comparison was made with a polymer named P3(TEG)T, which has a polar alkoxy linear chain. The UV-vis results indicated that the larger steric hindrances of the branched ethylene glycol side-chain in P3MBTEMT could inhibit its self-aggregation and had a stronger interaction with the SWCNTs compared to that of P3(TEG)T, which was also confirmed using Raman spectroscopy. When the mass ratio of SWCNTs to P3MBTEMT was 9:1 (represented as P3MBTEMT/SWCNTs-0.9), the composite film exhibited the highest thermoelectric properties with a power factor of 446.98 μW m−1 K−2, which was more than two times higher than that of P3(TEG)T/SWCNTs-0.9 (215.08 μW m−1 K−2). The output power of the thermoelectric device with P3MBTEMT/SWCNTs-0.9 was 2483.92 nW at 50 K, which was 1.66 times higher than that of P3(TEG)T/SWCNTs-0.9 (1492.65 nW). Furthermore, the P3MBTEMT/SWCNTs-0.5 showed superior mechanical properties compared to P3(TEG)T/SWCNTs-0.5. These results indicated that the mechanical and thermoelectric performances of polymer/SWCNT composites could be significantly improved by adding polar branched side-chains to conjugated polymers. This study provided a new strategy for creating high-performing novel flexible thermoelectric materials. Full article
(This article belongs to the Special Issue Advanced Biopolymer Materials)
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15 pages, 2268 KiB  
Article
Synthesis of Imidazolium Cations Linked to Para-t-Butylcalix[4]arene Frameworks and Their Use as Synthons for Nickel-NHC Complexes Tethered to Calix[4]arenes
by Michael J. Chetcuti, Haithem Naghmouchi, Abdelwaheb Hamdi and Lydia Karmazin
Molecules 2023, 28(15), 5697; https://doi.org/10.3390/molecules28155697 - 27 Jul 2023
Cited by 1 | Viewed by 1521
Abstract
A series of cationic p-tert-butylcalix[4]arenes, with side-arms that are functionalized with imidazolium groups, have been synthesized in good yields. The parent tetrahydroxy para-t-butyl-calix[4]arene was dialkylated at the phenolic hydrogen atoms using α,ω-dibromo-alkanes to yield bis(mono-brominated) alkoxy-chains of variable length. The brominated side-arms in [...] Read more.
A series of cationic p-tert-butylcalix[4]arenes, with side-arms that are functionalized with imidazolium groups, have been synthesized in good yields. The parent tetrahydroxy para-t-butyl-calix[4]arene was dialkylated at the phenolic hydrogen atoms using α,ω-dibromo-alkanes to yield bis(mono-brominated) alkoxy-chains of variable length. The brominated side-arms in these compounds were then further alkylated with substituted imidazoles (N-methylimidazole, N-(2,4,6-trimethyl-phenyl)imidazole, or N-(2,6-di-isopropylphenyl)imidazole) to yield a series of dicationic calixarenes with two imidazolium groups tethered, via different numbers of methylene spacers (n = 2–4), to the calixarene moiety. Related tetracationic compounds, which contain four imidazolium units linked to the calix[4]arene backbone, were also prepared. In all of these compounds, the NMR data show that the calixarenes adopted a cone configuration. All molecules were characterized by NMR spectroscopy and by MS studies. Single crystal X-ray diffraction studies were attempted on many mono-crystals of these cations, but significant disorder problems, partly caused by occluded solvent in the lattice, and lack of crystallinity resulting from partial solvent loss, precluded the good resolution of most X-ray structures. Eventually, good structural data were obtained from an unusually disordered single crystal of 5a, (1,3)-Cone-5,11,17,23-tetra-t-butyl-25,27-di-hydroxy-26,28-di-[2-(N-2,6-diisopropylphenyl-imidazolium)ethoxy]calix[4]arene dibromide and its presumed structure was confirmed. The structure revealed the presence of H-bonded interactions and some evidence of π-stacking. Some of these imidazolium salts were reacted with nickelocene to form the nickel N-heterocyclic carbene (NHC) complexes 7a7d. A bis-carbene nickel complex 8 was also isolated and its structure was established by single crystal X-ray diffraction studies. The structure was disordered and not of high quality, but the structural data corroborated the spectroscopic data. Full article
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13 pages, 1528 KiB  
Article
Mesomorphic Investigation of Binary Mixtures of Liquid Crystal Molecules with Different Mesogenic Architectonics
by Fowzia S. Alamro, Hoda A. Ahmed, Muna S. Khushaim, Noha S. Bedowr and Nada S. Al-Kadhi
Crystals 2023, 13(6), 899; https://doi.org/10.3390/cryst13060899 - 31 May 2023
Cited by 6 | Viewed by 2207
Abstract
Different binary phase diagrams, made from two differently substituted three-rings azo/ester and azomethine/ester compounds of the same terminal alkoxy side chain of six carbons, as opposed to the other terminal polar substituent, which can either donate electrons or withdraw electrons including H. The [...] Read more.
Different binary phase diagrams, made from two differently substituted three-rings azo/ester and azomethine/ester compounds of the same terminal alkoxy side chain of six carbons, as opposed to the other terminal polar substituent, which can either donate electrons or withdraw electrons including H. The thermal behavior of the prepared derivatives was investigated by differential scanning calorimetry and phases identified by polarized optical microscope. The first group of the binary mixtures was made from laterally F-substituted azo/ester derivatives and their laterally neat analogues. The second group of binary mixtures was made from laterally methoxy-substituted azomethine/ester derivatives and their laterally neat analogues. The final type of investigated phase diagrams was made from the laterally substituted azo and azomethine components bearing different lateral polar groups and different mesogenic moieties. Results were reviewed using phase diagrams that were produced and it was found that different mesomorphic characteristics were seen to depend on the mesogenic component as well as lateral and terminal polar groups. In all cases, these mixtures have been determined to have low melting-temperature eutectic compositions, while linear or negative deviation of nematic or smectic isotropic composition temperature dependence was observed. Full article
(This article belongs to the Special Issue Optical and Molecular Aspects of Liquid Crystals)
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14 pages, 2644 KiB  
Article
Preparation of Laterally Chloro-Substituted Schiff Base Ester Liquid Crystals: Mesomorphic and Optical Properties
by Violeta Jevtovic, Hoda A. Ahmed, Mohd Taukeer Khan, Salma A. Al-Zahrani, Najat Masood and Yassin Aweis Jeilani
Crystals 2023, 13(5), 835; https://doi.org/10.3390/cryst13050835 - 18 May 2023
Cited by 14 | Viewed by 2309
Abstract
A new class of Schiff base/ester compounds: ICln, 4-((2′-chlorophenylimino)methyl)phenyl-4″-alkoxy benzoates, were synthesized and their mesophase characteristics and thermal behavior were evaluated. Differential scanning calorimetry (DSC) was used to study mesophase transitions, and polarized optical microscopy was carried out to identify the phases (POM). [...] Read more.
A new class of Schiff base/ester compounds: ICln, 4-((2′-chlorophenylimino)methyl)phenyl-4″-alkoxy benzoates, were synthesized and their mesophase characteristics and thermal behavior were evaluated. Differential scanning calorimetry (DSC) was used to study mesophase transitions, and polarized optical microscopy was carried out to identify the phases (POM). The results show that all compounds are monomorphic, and enantiotropic nematic (N) phases were seen at all side chains. It was found that lateral Cl atoms in the terminal benzene ring influence both conformation and mesomorphic properties. Comparisons between the present investigated lateral Cl derivatives and their laterally neat, as well as their isomeric, compounds have been briefly discussed. Results revealed that the insertion of lateral Cl substituent in the molecular structure impacts the type and stability of the formed mesophases. The exchanges of the ester-connecting moiety improve their thermal nematic stability than their previously prepared structurally isomeric derivatives. These compounds exhibit a broad absorption in the UV-Visible region, including a peak in UV region and a tail around 550 nm, and there were observed to be absorption tail increases and energy band gap decreases with the increase of the alkoxy side chain length. The photoluminescence (PL) intensity was noted to be quenched for the bulky alkoxy group ascribed to non-radiative recombination through the defect states. Moreover, time resolved fluorescence decay spectra reveal that both the radiative and non-radiative recombination lifetime increases with the increase of alkoxy side chain length. Full article
(This article belongs to the Special Issue Optical and Molecular Aspects of Liquid Crystals)
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15 pages, 3486 KiB  
Article
Converting non-Mesogenic to Mesogenic Stacking of Amino-s-Triazine-Based Dendrons with p-CN Phenyl Unit by Eliminating Peripheral Dipole
by Yao-Chih Lu, Yu-Tsz Hsu, Tsung-Yen Yang, I-Chun Liou, Sheng-Wei Wang, Po-Chia Huang, Jey-Jau Lee, Long-Li Lai and Hsiu-Fu Hsu
Nanomaterials 2022, 12(2), 185; https://doi.org/10.3390/nano12020185 - 6 Jan 2022
Cited by 2 | Viewed by 1684
Abstract
Three new amino-s-triazine-based dendrons, 1a, 1b, and 1c, containing an aryl-CN moiety in the dendritic skeleton were prepared in 72–81% yields (1a: R1 = − N(n-C8H17)2, R [...] Read more.
Three new amino-s-triazine-based dendrons, 1a, 1b, and 1c, containing an aryl-CN moiety in the dendritic skeleton were prepared in 72–81% yields (1a: R1 = − N(n-C8H17)2, R2 = n-OC8H17, 1b: R1 = R2 = − N(n-C8H17)2, 1c: R1 = − N(n-C8H17)2, R2 = − N(n-C4H9)2). Dendrons 1a with N(n-C8H17)2 and n-OC8H17 peripheral substituents, surprisingly, did not show any mesogenic phase during the thermal process. However, non-mesogenic 1a can be converted to mesogenic 1b or 1c by eliminating the peripheral dipole arising from the alkoxy substituent; dendron 1b only comprising the same N(n-C8H17)2 peripheral groups showed a ~25 °C mesogenic range on heating and ~108 °C mesogenic range on cooling. In contrast, dendron 1c possessing different N(n-CmH2m+1)2 (m = 8 versus m = 4) peripheral units, having similar stacking as 1b, exhibited a columnar phase on thermal treatment, but its mesogenic range (~9 and ~66 °C on heating and cooling, respectively) was much narrower than that of 1b, attributed to 1c’s less flexible alkyl chains in the peripheral part of dendron. Dendron 1a with the alkoxy substituent in the peripheral skeleton, creating additional dipole correspondingly, thus, leads to the dendritic molecules having a non-mesogenic stacking. Without the peripheral dipole for intermolecular side-by-side interaction, dendrons 1b and 1c exhibit a columnar phase on thermal treatment because of the vibration from the peripheral alkyl chain. Full article
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17 pages, 2328 KiB  
Article
Synthesis, Fungitoxic Activity against Botrytis cinerea and Phytotoxicity of Alkoxyclovanols and Alkoxyisocaryolanols
by Adriana de Almeida Pinto Bracarense, Jociani Ascari, Giovanni Gontijo de Souza, Thays Silva Oliveira, Antonio Ruano-González, Ana A. Pinto, Maria Amélia Diamantino Boaventura, Jacqueline Aparecida Takahashi, Isidro G. Collado, Rosa Durán-Patrón and Antonio J. Macías-Sánchez
J. Fungi 2021, 7(12), 1079; https://doi.org/10.3390/jof7121079 - 15 Dec 2021
Cited by 1 | Viewed by 2516
Abstract
Clovane and isocaryolane derivatives have been proven to show several levels of activity against the phytopathogenic fungus Botrytis cinerea. Both classes of sesquiterpenes are reminiscent of biosynthetic intermediates of botrydial, a virulence factor of B. cinerea. Further development of both classes [...] Read more.
Clovane and isocaryolane derivatives have been proven to show several levels of activity against the phytopathogenic fungus Botrytis cinerea. Both classes of sesquiterpenes are reminiscent of biosynthetic intermediates of botrydial, a virulence factor of B. cinerea. Further development of both classes of antifungal agent requires exploration of the structure–activity relationships for the antifungal effects on B. cinerea and phytotoxic effects on a model crop. In this paper, we report on the preparation of a series of alkoxy-clovane and -isocaryolane derivatives, some of them described here for the first time (2b, 2d, 2f2h, and 4c4e); the evaluation of their antifungal properties against B. cinerea, and their phytotoxic activites on the germination of seeds and the growth of radicles and shoots of Lactuca sativa (lettuce). Both classes of compound show a correlation of antifungal activity with the nature of side chains, with the best activity against B. cinerea for 2d, 2h, 4c and 4d. In general terms, while 2-alkoxyclovan-9-ols (2a2e) exert a general phytotoxic effect, this is not the case for 2-arylalkoxyclovan-9-ols (2f2i) and 8-alkoxyisocaryolan-9-ols (4a4d), where stimulating effects would make them suitable candidates for application to plants. Full article
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10 pages, 1720 KiB  
Article
Thermal and Mesomorphic Investigations of 1:1 Supramolecular Assemblies of 4-[(4-(n-Alkoxy)phenylimino)methyl]benzoic Acids Having Symmetrical and Un-Symmetrical Terminal Chain Lengths
by Fowzia S. Alamro, Hoda A. Ahmed, Ayman M. Mostafa and Magdi M. Naoum
Symmetry 2021, 13(10), 1785; https://doi.org/10.3390/sym13101785 - 25 Sep 2021
Cited by 9 | Viewed by 2461
Abstract
Thermal and mesomorphic properties of possible 1:1 supramolecular complexes (SMCs) (Im/In) designed from two members of 4-[(4-(n-alkoxy)phenylimino)methyl]benzoic acid with symmetrical or un-symmetrical alkoxy terminal flexible chains (carbons of m and n = 6, 8 and 16), were analyzed [...] Read more.
Thermal and mesomorphic properties of possible 1:1 supramolecular complexes (SMCs) (Im/In) designed from two members of 4-[(4-(n-alkoxy)phenylimino)methyl]benzoic acid with symmetrical or un-symmetrical alkoxy terminal flexible chains (carbons of m and n = 6, 8 and 16), were analyzed by differential scan-calorimetry (DSC), thermogravemetric (TG) analysis, and their mesophases identified by polarized optical microscopy (POM). The equimolecular mixtures of the two acids possess symmetrical and un-symmetrical terminal lengths. The mesomorphic properties of the binary mixtures were examined as a function of the total alkoxy chain length on both sides. Results revealed that the nematic mesophase temperature range increases as the total terminal length increases for all designed un-symmetrical mixtures. A comparison was constructed between the formed SMCs and of those of the previously prepared 4-n-alkoxyphenylazo benzoic acids as well as the 4-n-alkoxy benzoic acids, to examine the impact of mesogenic core on the mesomorphic properties. The comparison indicated that as the mesogenic portion lengthens the thermal mesophase stability exhibits higher values of phase transition temperatures; whereas, the azo and Schiff base moieties exhibited near thermal properties. Full article
(This article belongs to the Section Chemistry: Symmetry/Asymmetry)
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15 pages, 4485 KiB  
Article
Pyridine-Based Three-Ring Bent-Shape Supramolecular Hydrogen Bond-Induced Liquid Crystalline Complexes: Preparation and Density Functional Theory Investigation
by Sayed Z. Mohammady, Daifallah M. Aldhayan and Mohamed Hagar
Crystals 2021, 11(6), 628; https://doi.org/10.3390/cryst11060628 - 31 May 2021
Cited by 15 | Viewed by 3801
Abstract
A series of new supramolecular three-ring bent-shape Schiff base liquid crystal (LC) complexes were prepared and studied. On one side, two alkoxy chain lengths of the carboxylic acids were used, namely eight and sixteen carbons. Moreover, on the other side, terminal small compact [...] Read more.
A series of new supramolecular three-ring bent-shape Schiff base liquid crystal (LC) complexes were prepared and studied. On one side, two alkoxy chain lengths of the carboxylic acids were used, namely eight and sixteen carbons. Moreover, on the other side, terminal small compact groups, which substituted aniline, with different polarities were utilized. Furthermore, the hydrogen-bonding interactions in the formed complexes were elucidated by Fourier-transform infrared (FT–IR) spectroscopy. The mesomorphic thermal and optical characteristics of the samples were determined by differential thermal analysis (DSC) and polarized optical microscopy (POM). The complexes exhibited enantiotropic and dimorphic mesophase behaviors. The results indicate that the polarity of the compact groups and the lengths of the alkoxy chains greatly impacted the mesomorphic characteristics and thermal stabilities of the mesophases. The observed values of the enthalpy changes (ΔH) associated with the crystalline smectic-A (TCr-SmA) transitions were extremely small compared with the conventional values that characterize supramolecular hydrogen-bonded liquid crystalline complexes. ΔH, which corresponded to the nematic isotropic transitions (TN-I), varied from 0.13 to 9.54 kJ/mol depending mainly on the polarity of the groups that were para-attached to the aniline moiety. Finally, the theoretical results obtained by density functional theory (DFT) calculations were discussed. The DFT geometrical structures showed non-coplanar structures. The mesomorphic range was correlated with the calculated dipole moment, polarizability and the aspect ratios of the investigated compounds. Full article
(This article belongs to the Special Issue Self-Assembly in Liquid Crystalline Materials)
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16 pages, 5753 KiB  
Article
Electrochemical and Spectroelectrochemical Studies on the Reactivity of Perimidine–Carbazole–Thiophene Monomers towards the Formation of Multidimensional Macromolecules versus Stable π-Dimeric States
by Malgorzata Czichy, Patryk Janasik, Pawel Wagner, David L. Officer and Mieczyslaw Lapkowski
Materials 2021, 14(9), 2167; https://doi.org/10.3390/ma14092167 - 23 Apr 2021
Cited by 8 | Viewed by 3022
Abstract
During research on cross-linked conducting polymers, double-functionalized monomers were synthesized. Two subunits potentially able to undergo oxidative coupling were used—perimidine and, respectively, carbazole, 3,6-di(hexylthiophene)carbazole or 3,6-di(decyloxythiophene)carbazole; alkyl and alkoxy chains as groups supporting molecular ordering and 14H-benzo[4,5]isoquinone[2,1-a]perimidin-14-one segment promoting CH⋯O interactions [...] Read more.
During research on cross-linked conducting polymers, double-functionalized monomers were synthesized. Two subunits potentially able to undergo oxidative coupling were used—perimidine and, respectively, carbazole, 3,6-di(hexylthiophene)carbazole or 3,6-di(decyloxythiophene)carbazole; alkyl and alkoxy chains as groups supporting molecular ordering and 14H-benzo[4,5]isoquinone[2,1-a]perimidin-14-one segment promoting CH⋯O interactions and π–π stacking. Electrochemical, spectroelectrochemical, and density functional theory (DFT) studies have shown that potential-controlled oxidation enables polarization of a specific monomer subunit, thus allowing for simultaneous coupling via perimidine and/or carbazole, but mainly leading to dimer formation. The reason for this was the considerable stability of the dicationic and tetracationic π-dimers over covalent bonding. In the case of perimidine-3,6-di(hexylthiophene)carbazole, the polymer was not obtained due to the steric hindrance of the alkyl substituents preventing the coupling of the monomer radical cations. The only linear π-conjugated polymer was obtained through di(decyloxythiophene)carbazole segment from perimidine-di(decyloxythiophene)-carbazole precursor. Due to the significant difference in potentials between subsequent oxidation states of monomer, it was impossible to polarize the entire molecule, so that both directions of coupling could be equally favored. Subsequent oxidation of this polymer to polarize the side perimidine groups did not allow further crosslinking, because rather the π–π interactions between these perimidine segments dominate in the solid product. Full article
(This article belongs to the Special Issue Conducting Polymers: Recent Progress and New Functions)
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22 pages, 1907 KiB  
Article
Dibasic Derivatives of Phenylcarbamic Acid as Prospective Antibacterial Agents Interacting with Cytoplasmic Membrane
by Šárka Pospíšilová, Ivan Malík, Kristyna Bezouskova, Tereza Kauerova, Peter Kollar, Jozef Csöllei, Michal Oravec, Alois Cizek and Josef Jampilek
Antibiotics 2020, 9(2), 64; https://doi.org/10.3390/antibiotics9020064 - 6 Feb 2020
Cited by 6 | Viewed by 3584
Abstract
1-[2-[({[2-/3-(Alkoxy)phenyl]amino}carbonyl)oxy]-3-(dipropylammonio)propyl]pyrrolidinium/azepan- ium oxalates or dichlorides (alkoxy = butoxy to heptyloxy) were recently described as very promising antimycobacterial agents. These compounds were tested in vitro against Staphylococcus aureus ATCC 29213, Enterococcus faecalis ATCC 29212 (reference and control strains), three methicillin-resistant isolates of S. aureus [...] Read more.
1-[2-[({[2-/3-(Alkoxy)phenyl]amino}carbonyl)oxy]-3-(dipropylammonio)propyl]pyrrolidinium/azepan- ium oxalates or dichlorides (alkoxy = butoxy to heptyloxy) were recently described as very promising antimycobacterial agents. These compounds were tested in vitro against Staphylococcus aureus ATCC 29213, Enterococcus faecalis ATCC 29212 (reference and control strains), three methicillin-resistant isolates of S. aureus, and three isolates of vancomycin-resistant E. faecalis. 1-[3-(Dipropylammonio)-2-({[3-(pentyloxy-/hexyloxy-/heptyloxy)phenyl]carbamoyl}oxy)propyl]pyrrolidinium dichlorides showed high activity against staphylococci and enterococci comparable with or higher than that of used controls (clinically used antibiotics and antiseptics). The screening of the cytotoxicity of the compounds as well as the used controls was performed using human monocytic leukemia cells. IC50 values of the most effective compounds ranged from ca. 3.5 to 6.3 µM, thus, it can be stated that the antimicrobial effect is closely connected with their cytotoxicity. The antibacterial activity is based on the surface activity of the compounds that are influenced by the length of their alkoxy side chain, the size of the azacyclic system, and hydro-lipophilic properties, as proven by in vitro experiments and chemometric principal component analyses. Synergistic studies showed the increased activity of oxacillin, gentamicin, and vancomycin, which could be explained by the direct activity of the compounds against the bacterial cell wall. All these compounds demonstrate excellent antibiofilm activity, when they inhibit and disrupt the biofilm of S. aureus in concentrations close to minimum inhibitory concentrations against planktonic cells. Expected interactions of the compounds with the cytoplasmic membrane are proven by in vitro crystal violet uptake assays. Full article
(This article belongs to the Special Issue Novel Strategies against Pathogenic Bacteria)
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14 pages, 3044 KiB  
Article
Poly(phenylene methylene)-Based Coatings for Corrosion Protection: Replacement of Additives by Use of Copolymers
by Marco F. D’Elia, Mirko Magni, Stefano P. M. Trasatti, Thomas B. Schweizer, Markus Niederberger and Walter Caseri
Appl. Sci. 2019, 9(17), 3551; https://doi.org/10.3390/app9173551 - 29 Aug 2019
Cited by 11 | Viewed by 5188
Abstract
Poly(phenylene methylene) (PPM) is a thermally stable, hydrophobic, fluorescent hydrocarbon polymer. Recently, blended PPM has been proposed as a valuable anti-corrosion coating material, and, in particular, rheological additives such as external plasticizers resulted crucial to prevent crack formation. Accordingly, to avoid common problems [...] Read more.
Poly(phenylene methylene) (PPM) is a thermally stable, hydrophobic, fluorescent hydrocarbon polymer. Recently, blended PPM has been proposed as a valuable anti-corrosion coating material, and, in particular, rheological additives such as external plasticizers resulted crucial to prevent crack formation. Accordingly, to avoid common problems related to the use of external plasticizers, the development of PPM-related copolymer-based coatings containing n-octyloxy side chains and their anti-corrosion behavior were explored in this study. The aluminum alloy AA2024, widely employed for corrosion studies, was selected as a substrate, covered with a thin layer of a polybenzylsiloxane in order to improve adhesion between the underlying hydrophilic substrate and the top hydrophobic coating. Gratifyingly, coatings with those copolymers were free of bubbles and cracks. The n-octyloxy side-chains may be regarded to adopt the role of a bound plasticizer, as the glass transition temperature of the copolymers decreases with increasing content of alkoxy side-chains. Electrochemical corrosion tests on PPM-substituted coatings exhibited good corrosion protection of the metal surface towards a naturally aerated near-neutrally 3.5% wt.% NaCl neutral solution, providing comparable results to blended PPM formulations, previously reported. Hence, the application of rheological additives can be avoided by use of proper design copolymers. Full article
(This article belongs to the Special Issue Advances in Organic Corrosion Inhibitors and Protective Coatings)
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19 pages, 7737 KiB  
Article
Improved Electronic Transport in Ion Complexes of Crown Ether Based Columnar Liquid Crystals
by Peter Staffeld, Martin Kaller, Philipp Ehni, Max Ebert, Sabine Laschat and Frank Giesselmann
Crystals 2019, 9(2), 74; https://doi.org/10.3390/cryst9020074 - 31 Jan 2019
Cited by 17 | Viewed by 6084
Abstract
The Li+- and K+-complexes of new discotic mesogens, where two n-alkoxy-substituted triphenylene cores are connected by a central crown ether (12-crown-4 and 18-crown-6), provide interesting structural and electronic properties. The inter- and intra-columnar structure was investigated by small and [...] Read more.
The Li+- and K+-complexes of new discotic mesogens, where two n-alkoxy-substituted triphenylene cores are connected by a central crown ether (12-crown-4 and 18-crown-6), provide interesting structural and electronic properties. The inter- and intra-columnar structure was investigated by small and wide angle X-ray scattering. The electronic and ionic transports were studied by temperature dependent photoconductivity and impedance spectroscopy, respectively. Besides a strong increase of the stability and the width of the columnar phases the presence of soft anions (iodide, thiocyanate, tetrafluoroborate) leads to an improved intra-columnar order. The hereby shortened stacking-distance of the triphenylene cores leads to a significant increase of the photoconductivity in the columnar mesophase. Furthermore, the ionic conductivity of the new materials was investigated on macroscopically aligned thin films. The existence of channels for fast cation transport formed by the stacked crown ether moieties in the centre of each column can be excluded. The cations are coordinated strongly and therefore contributing only little to the conductivity. The ionic conductivity is dominated by the anisotropic migration of the non-coordinated anions through the liquid, like side chains favouring the propagation parallel to the columns. Iodide migrates about 20 times faster than thiocyanate and 100 times faster than tetrafluoroborate. Full article
(This article belongs to the Special Issue Ionic Liquid Crystals)
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19 pages, 9074 KiB  
Article
Soluble Electrochromic Polymers Incorporating Benzoselenadiazole and Electron Donor Units (Carbazole or Fluorene): Synthesis and Electronic-Optical Properties
by Jianzhong Xu, Qi Ji, Lingqian Kong, Hongmei Du, Xiuping Ju and Jinsheng Zhao
Polymers 2018, 10(4), 450; https://doi.org/10.3390/polym10040450 - 17 Apr 2018
Cited by 28 | Viewed by 4597
Abstract
A series of π-conjugated polymers containing alternating benzoselenadiazole (BSe)-bi(thiophene derivative)-carbazole or benzoththiadiazole (BSe)-bi(thiophene derivative)-fluorene units were designed and synthesized. Thiophene derivatives, namely 3-hexylthiophene, 3,4-bihexyloxythiophene, and 3,4-bioctyloxythiophene, were used as the π-bridges of the polymers. The polymers were characterized in detail in terms of [...] Read more.
A series of π-conjugated polymers containing alternating benzoselenadiazole (BSe)-bi(thiophene derivative)-carbazole or benzoththiadiazole (BSe)-bi(thiophene derivative)-fluorene units were designed and synthesized. Thiophene derivatives, namely 3-hexylthiophene, 3,4-bihexyloxythiophene, and 3,4-bioctyloxythiophene, were used as the π-bridges of the polymers. The polymers were characterized in detail in terms of their thermal stabilities, cyclic voltammograms, UV-Vis absorption, spectroelectrochemistry, dynamic switching property and so forth. The alkoxy thiophene π-bridged polymers have lower onset oxidation potentials and bandgaps than that of their corresponding alkyl thiophene π-bridged polymers. The selection of the donor units between the carbazole and the fluorene units has nearly no effect on the bandgaps and colors as well as the onset oxidation potentials of the polymers. The increase in the length of the side alkyl chains on the thiophene ring caused a slight increase in the polymer bandgap, which may be caused by the space hindrance effect. The dynamic switching abilities of the polymers were obtained by the chronoabsorptometry method, and the results also suggested that the alkoxy thiophene-containing polymers (as π-bridges) have higher contrast ratios than the corresponding alkyl thiophene-containing polymers. Furthermore, the increase in the length of the side alkyl chain might have a detrimental effect on the optical contrast ratios of the polymers. Full article
(This article belongs to the Special Issue Electrochromic Polymers)
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