Alkyl Side Chains Research Articles

Cannabinoids as Antibacterial Agents: A Systematic and Critical Review of In Vitro Efficacy Against Streptococcus and Staphylococcus

Background: Two major bacterial pathogens, Staphylococcus aureus and Streptococcus pyogenes, are becoming increasingly antibiotic-resistant. Despite the urgency, only a few new antibiotics have been approved to address these infections. Although cannabinoids have been noted for their antibacterial properties, a comprehensive review of their effects on these bacteria has been lacking. Objective: This systematic review examines the antibacterial activity of cannabinoids against S. aureus, including methicillin-resistant S. aureus (MRSA) and vancomycin-resistant S. aureus (VRSA) strains, and S. pyogenes. Methods: Databases, including CINAHL, Cochrane, Medline, Scopus, Web of Science, and LILACS, were searched. Of 3510 records, 24 studies met the inclusion criteria, reporting on the minimum inhibitory concentration (MIC) and minimum bactericidal concentration of cannabinoids. Results: Cannabidiol (CBD) emerged as the most effective cannabinoid, with MICs ranging from 0.65 to 32 mg/L against S. aureus, 0.5 to 4 mg/L for MRSA, and 1 to 2 mg/L for VRSA. Other cannabinoids, such as cannabichromene, cannabigerol (CBG), and delta-9-tetrahydrocannabinol (Δ9-THC), also exhibited significant antistaphylococcal activity. CBD, CBG, and Δ9-THC also showed efficacy against S. pyogenes, with MICs between 0.6 and 50 mg/L. Synergistic effects were observed when CBD and essential oils from Cannabis sativa when combined with other antibacterial agents. Conclusion: Cannabinoids’ antibacterial potency is closely linked to their structure–activity relationships, with features like the monoterpene region, aromatic alkyl side chain, and aromatic carboxylic groups enhancing efficacy, particularly in CBD and its cyclic forms. These results highlight the potential of cannabinoids in developing therapies for resistant strains, though further research is needed to confirm their clinical effectiveness.

Effect of Hydrophobic Acrylic Monomers with Different Alkyl Side Chain Lengths on Reducing the Glistening of Hydrophobic Acrylic Intraocular Lens Materials

AbstractGlistening is the condensation of water that forms within the intraocular lens (IOL) materials. In this study, a new approach was attempted to reduce the glistening of IOL materials by introducing hydrophobic acrylic monomers with different alkyl side chain lengths into the IOL materials. Various hydrophobic acrylic monomers such as butyl acrylate (BA), 2‐ethylhexyl acrylate (EHA), and dodecyl acrylate (DA) were copolymerized with a hydrophobic acrylic monomer, 2‐phenoxyethyl acrylate, respectively. In this process, we investigated the effect of the alkyl side chain lengths of hydrophobic acrylic monomers on the glistening of hydrophobic acrylic IOL materials. As the content of hydrophobic acrylic monomers (BA, EHA, and DA) increased, the glistening of IOL materials decreased significantly for all hydrophobic acrylic monomers. At the same content of hydrophobic acrylic monomers, the IOL material showed the least content of glistening when copolymerized with DA. However, the IOL material obtained using BA exhibited the largest content of glistening, indicating that the glistening reduction effect was large in the order of DA>EHA>BA. These findings show that the glistening of IOL materials decreases with increasing alkyl side chain lengths of hydrophobic acrylic monomers.

Halogen‐free solvent processed organic solar sub‐modules (≈55 cm2) with 14.70% efficiency by controlling the morphology of alkyl chain engineered polymer donor

AbstractGoals of high efficiency, morphological analysis, and the ability to produce organic solar cell (OSC) sub‐modules using halogen‐free solvents are demanding. In this study, a robust conjugated polymer with thienothiophene π‐spacer with pendant alkyl side chain (NapBDT‐C12) was synthesized and used to fabricate sub‐modules. Excellent efficiencies were demonstrated by a NapBDT‐C12 integrated ternary blend, which was used to produce stable small‐area‐to‐sub‐module devices using O‐xylene. The efficiency of the NapBDT‐C12 added small‐area ternary devices (PM6:NapBDT‐C12:L8‐BO) was 18.71%. Owing to the controlled homogeneity of the blend with favorable nanoscale film morphology, enhanced carrier mobilities, and exciton dissociation/splitting properties, contributed to the efficiencies of small‐area‐to‐sub‐module OSCs. Moreover, a 55 cm2 sub‐module with an efficiency of 14.69% was accomplished by bar coating using O‐xylene under ambient conditions. This study displays the potential of a ternary blend based OSC device to produce high efficiency scalable sub‐modules at ambient conditions.image

Effects of Alkyl Side Chain Length on the Structural Organization and Proton Conductivity of Sulfonated Polyimide Thin Films

Effects of Alkyl Side Chain Length on the Structural Organization and Proton Conductivity of Sulfonated Polyimide Thin Films

Intrinsic role of alkyl side chains in disorder, aggregates, and carrier mobility of nonfullerene acceptors for organic solar cells: A multiscale theoretical study

Intrinsic role of alkyl side chains in disorder, aggregates, and carrier mobility of nonfullerene acceptors for organic solar cells: A multiscale theoretical study

Molecular Ordering Manipulation in Fused Oligomeric Mixed Conductors for High-Performance n-Type Organic Electrochemical Transistors.

Advanced n-type organic electrochemical transistors (OECTs) play an important part in bioelectronics, facilitating the booming of complementary circuits-based biosensors. This necessitates the utilization of both n-type and p-type organic mixed ionic-electronic conductors (OMIECs) exhibiting a balanced performance. However, the observed subpar electron charge transport ability in most n-type OMIECs presents a significant challenge to the overall functionality of the circuits. In response to this issue, we achieve high-performance OMIECs by leveraging a series of fused electron-deficient monodisperse oligomers with mixed alkyl and glycol chains. Through molecular ordering manipulation by optimizing of their alkyl side chains, we attained a record-breaking OECT electron mobility of 0.62 cm2/(V s) and μC* of 63.2 F/(cm V s) for bgTNR-3DT with symmetrical alkyl chains. Notably, the bgTNR-3DT film also exhibits the highest structural ordering, smallest energetic disorder, and the lowest trap density among the series, potentially explaining its ideal charge transport property. Additionally, we demonstrate an organic inverter incorporating bgTNR-3DT OECTs with a gain above 30, showcasing the material's potential for constructing organic circuits. Our findings underscore the indispensable role of alkyl chain optimization in the evolution of prospective high performance OMIECs for constructing advanced organic complementary circuits.

Hydrophobic assembly of molecular catalysts at the gas-liquid-solid interface drives highly selective CO2 electromethanation.

Molecular catalysts offer tunable active and peripheral sites, rendering them ideal model systems to explore fundamental concepts in catalysis. However, hydrophobic designs are often regarded as detrimental for dissolution in aqueous electrolytes. Here we show that established cobalt terpyridine catalysts modified with hydrophobic perfluorinated alkyl side chains can assemble at the gas-liquid-solid interfaces on a gas diffusion electrode. We find that the self-assembly of these perfluorinated units on the electrode surface results in a catalytic system selective for electrochemical CO2 reduction to CH4, whereas every other cobalt terpyridine catalyst reported previously was only selective for CO or formate. Mechanistic investigations suggest that the pyridine units function as proton shuttles that deliver protons to the dynamic hydrophobic pocket in which CO2 reduction takes place. Finally, integration with fluorinated carbon nanotubes as a hydrophobic conductive scaffold leads to a Faradaic efficiency for CH4 production above 80% at rates above 10 mA cm-2-impressive activities for a molecular electrocatalytic system.

Ni-catalysed remote C(sp3)-H functionalization using chain-walking strategies.

The dynamic translocation of a metal catalyst along an alkyl side chain - often coined as 'chain-walking' - has opened new retrosynthetic possibilities that enable functionalization at unactivated C(sp3)-H sites. The use of nickel complexes in chain-walking strategies has recently gained considerable momentum owing to their versatility for forging sp3 architectures and their redox promiscuity that facilitates both one-electron or two-electron reaction manifolds. This Review discusses the relevance and impact that these processes might have in synthetic endeavours, including mechanistic considerations when appropriate. Particular emphasis is given to the latest discoveries that leverage the potential of Ni-catalysed chain-walking scenarios for tackling transformations that would otherwise be difficult to accomplish, including the merger of chain-walking with other new approaches such asphotoredox catalysis or electrochemical activation.

Impact of side chain length on the properties and alkaline fuel cell performance of OEG-grafted poly(terphenyl piperidinium) anion exchange membranes

In designing comb-shaped anion exchange membranes (AEMs), replacing alkyl side chains with ethylene glycol (EG)-based ones significantly enhances membrane properties and boosts AEM fuel cell performance. Although much research has focused on optimizing the placement of EG segments within the polymer matrix, the effect of EG chain length remains less explored. In this work, a series of poly(terphenyl piperidinium) AEMs with N-oligo(ethylene glycol) (OEG) terminal pendants having two to five EG repeating units were prepared by simple post-polymerization quaternization. The membrane properties showed a strong correlation with the length of the OEG side chains, influenced by both chemical composition and phase behavior. Among the OEG-grafted AEMs, PTP-OEG3 with moderate three EG repeating units, exhibited the best properties due to a careful balance between EG and cationic groups, leading to a favorable microphased separation. It achieved high hydroxide conductivity (114 mS cm−1 at 80 °C in water), robust mechanical strength (tensile strength >52 MPa), and good ex situ alkaline stability. As a result, the AEM fuel cells with the property-balanced PTP-OEG3 membrane achieved the highest peak power density of 976 mW cm−2. The in situ stability of these AEMs was also investigated. Evidently, understanding the optimal EG side chain length is an important criterion for designing AEM materials for alkaline fuel cells.

Mechanism study on rheological response of thermally pretreated waxy crude oil

Pre-heating treatment significantly influences the low-temperature flow characteristics of waxy crude oil, yet its underlying mechanism warrants further investigation. This study explores the effects of pre-heating temperatures (60–110 °C) on the rheological characteristics of waxy crude oil from Nanyang using 1H NMR, DSC, Microscopic Observation, and Rheological Property Test. Findings reveal that asphaltenes increasingly dissolve at the pre-heating temperature of 70 °C, improving their capacity to act as nucleation sites for wax crystals. Consequently, the wax appearance temperature (WAT) increases. Meanwhile, the rheological parameters of the crude oil decrease and wax crystals exhibit smaller and tighter rod-like structures. Further growing the pre-heating temperature to 80 °C induces a comprehensive effect: alterations in asphaltene polarity, hindrance of asphaltene aggregation by alkyl side chains, and self-aggregation of alkyl side chains. This results in decreased WAT, along with the lowest rheological parameter values, with wax crystals appearing as the smallest and tightest dot-like shapes. At 80 °C, the optimal ratio between asphaltene polarity and alkyl side chain characteristics promotes strong nucleation and co-crystallization between asphaltene and wax crystals, maximizing asphaltene's ability to enhance the crude oil's low-temperature flowability. However, as the pre-heating temperature continues to rise, WAT decreases slightly and the rheological response starts to deteriorate.

Surfactant-Free Preparation of Conjugated Polymer Nanoparticles in Aqueous Dispersions Using Sulfate Functionalized Fluorene Monomers.

Conjugated polymer nanoparticles (CPNs) can be synthesized by a Suzuki-Miyaura cross-coupling miniemulsion polymerization to give stable dispersions with a high concentration of uniform nanoparticles. However, large amounts of added surfactants are required to stabilize the miniemulsion and prevent the aggregation of the nanoparticles. Removal of the excess surfactant is challenging, and residual surfactant in thin films deposited from these dispersions can reduce the performance of optoelectronic devices. We report a novel approach to prepare stable dispersions with no added surfactant using a fluorene monomer, 2,7-dibromo-9,9-bis(undecanesulfate)-9H-fluorene, with alkyl side chains terminated by negatively charged sulfate groups. This functionality mimics the structure of one of the most commonly used surfactants, sodium dodecyl sulfate (SDS). This charged monomer effectively stabilizes the miniemulsion through electrostatic repulsion without the use of any additional surfactant in molar ratios ranging from 2.0 to 20.0 mol % of total monomer content for the preparation of poly(9,9-dioctylfluorene) (PFO) and poly(9,9-dioctylfluorene-alt-bithiophene) (PF8T2). Incorporation of 5.0 mol % of the amphiphilic monomer gave stable dispersions with a surface potential below -40 mV and, and polymers with molar mass (Mn) above 10 kg mol-1. This method should be generally applicable to the preparation of dispersions of polyfluorenes for application in organic electronic and optoelectronic devices without the requirement for time-consuming processes to remove residual surfactant.

Cationic effect study in acetate-based ionic liquids/ZIF-8 composites for CO2 sorption

Several strategies can be considered for the mitigation of carbon dioxide (CO2) emissions to the atmosphere, and among them is its post-combustion capture/separation from flue gas emitted from coal-fired power plants. In this work, six imidazolium, ammonium- and DABCO-based ionic liquids (ILs) containing the acetate anion were used to impregnate the metal-organic framework (MOF) ZIF-8. The cationic effect was studied to determine how the different cationic families and side alkyl chain size influence the gas sorption performance of the produced IL@MOF composites. The combination of different characterization techniques confirmed IL impregnation, and that the composite materials were microporous and crystalline. Single-component CO2 and nitrogen (N2) sorption-desorption equilibrium measurements were performed at 303 K for ZIF-8 and the IL@ZIF-8 materials. At the low-pressure regime (0–1 bar), synergy was observed for the imidazolium-based composites, especially for the one with the long-side alkyl chain. The ideal CO2/N2 selectivity was calculated for post-combustion composition, and, at 1 bar, [C10MIM][Ac]@ZIF-8 was over four times more selective than ZIF-8, while the selectivity of [C2MIM][Ac]@ZIF-8 at this pressure almost tripled when compared to the MOF. A chemical reaction between CO2 and the imidazolium ILs explained the results.

Supramolecular blends of C-alkylpyrogallol[4]arenes and polytetrahydrofurans

A small series of the amphiphilic macrocycles – C-alkylpyrogallol[4]arenes has been synthesized and examined by single crystal X-ray analysis which showed the formation of two supramolecular arrangements depending on solvent used for crystallization, i.e., multilayered motif and hexameric capsule. Those structural findings provided an insight into blends prepared from aforementioned macrocycles and various polytetrahydrofurans (polyTHFs). Thus, 1:1 wt ratio mixtures were obtained and investigated by combination of Fourier-transform infrared spectroscopy (FT-IR), differential scanning calorimetry (DSC), and thermogravimetric analysis (TGA). As it turned out, the viscosity of these blends was increased compared to starting materials, which imply that pyrogallol[4]arenes can be successfully utilized as supramolecular cross-linkers enhancing H-bonding between adjacent macromolecular chains. As the major difference between compounds synthesized is the length and geometry of their respective alkyl side chains attached directly to macrocyclic core, i.e., n-propyl- and cyclohexyl- vs. n-dodecyl-, it seemed likely that even insignificant increase in their hydrophobicity can induce high order aggregation of nanoparticles in the slurries, thus affecting their viscosity. Overall, material viscoelastic properties are tunable at macroscopic level by choosing particular pyrogallol[4]arene/solvent combination and adjusting the temperature, which may be advantageous for the design of hybrid materials.

Polymer coating by oxidative polymerization of a new dopamine analogue with two amino groups

In our quest to expand the comprehensive chemistry of polydopamine and its catechol-containing analogous adhesive polymers we developed a new monomer, specifically 4-[3-amino-2-(aminomethyl)propyl]benzene-1,2-diol ADA. This compound is an analogue of dopamine characterized by an elongated and branched alkyl side chain that incorporates two amino groups. ADA was synthesized in two steps from 3,4-dihydroxybenzaldehyde in high yields. Exposure to air in aqueous Tris solution initiated polymerization leading to a dark colored product PADA that can adhere to surfaces forming continuous layers. The product was analyzed by FTIR, NMR, UV–vis-spectroscopy, AFM, HR-ESI-MS spectrometry, XPS, DPV, DLS and contact angle measurement. Based on these analyses, a general structure of the product is proposed as along with a mechanism of its formation. Notably, the properties of PADA are distinct from those of polydopamine offering different potential application. In particular, the additional amino groups could be used for interesting linkage of other functional moieties.

Bifunctionalized MOFs modified poly (aryl ether ketone sulfone) ultrafiltration membranes with high-efficient BSA separation and dye adsorption

In this study, by connecting the amino ligand in ZIF-8-NH2 with an alkyl side chain containing sulfonic acid groups in a one-step method, a novel nanofiller (ZIF-8-NS) with bifunctional amino and sulfonic acid groups was formed. Sulfonated poly (aryl ether ketone sulfone) containing fluorene group (F-SPAEKS) was chosen as the polymer matrix. The nanofiller not only had good hydrophilicity but also had electrostatic interaction with the polymer matrix, which effectively promoted the compatibility problem among the polymer matrix and the filler. The nanofillers were characterized by XRD, FT-IR, SEM and XPS. The composite membranes were prepared by the NIPs method. The antifouling and separation properties of the prepared mixed matrix membranes (MMMs) were investigated using positively charged dye (RHB) and negative charge bovine serum albumin (BSA) as model contaminants. The water flux of the pure membrane achieved 529.16 L/m2 h. When the addition amount of ZIF-8-NS was 0.1 %, the water flux of M4 (F-SPAEKS/ZIF-8-NS-0.1 %) could reach 838.84 L/m2 h. The retention rate of the BSA solution could reach 99.06 %, and the FRR value was kept at a high level (81.45 %). Meanwhile, the dynamic retention of M4 on the primary adsorption of the dye RHB could even reach 99.89 %. Therefore, the innovative design of the novel MMMs not only improved the flux, retention, and other separation properties but also enhanced their excellent adsorption capacity for RHB dyes. This result indicated that the nanofiller ZIF-8-NS provided an interesting reference for the study of ultrafiltration membranes.

Bio-based liquid crystal epoxy resins: Toughening and strengthening of conventional epoxy resins with strategically extended spacer layers

Liquid crystal epoxy resin, as an ideal toughening agent, combines the features of liquid crystal ordering and network cross-linking, which can effectively optimize the comprehensive performance of blended epoxy resins and achieve an ideal balance of rigidity and toughness. Here we successfully synthesized rigid and flexible bio-based liquid crystal epoxy resin (THBR-EP) by finely tuning the length of alkyl side chains. Using aromatic diamine as curing agent, a homogeneous network without phase separation was constructed by taking advantage of the different activity but good compatibility with ordinary epoxy resins, which significantly improved the toughness of the blended system. Specifically, only a small amount of THBR-EP(2.5 wt%) was required to exhibit a maximum impact strength of 48.8 kJ/m2. Moreover, the increase in system toughness was accompanied by a benign improvement in flexural strength, modulus and thermal stability. The ordered structure of the liquid crystals and their good compatibility with the resin matrix enhanced the ability to inhibit crack extension and energy dissipation. The feasibility to simultaneously achieve effective toughening and other property improvements of common resins broadens the application of resins under various demanding scenarios.

Micellar structure of decenyl succinic anhydride modified pullulan with degree of substitution dependence in aqueous solution

A broad distribution pullulan (PUL) sample was hydrophobically modified by a relative longer decenyl succinic anhydride (DCSA) side chains with seven different degree of substitution (DS) to obtain the PUL-DCSA. The micellar structure of PUL-DCSA with DS dependence was investigated by pyrene-probe fluorescence and small-angle X-ray scattering (SAXS) in 0.05 M aqueous NaCl. While PUL-DCSA with DS > 0.26, both the SAXS and fluorescence results can be explained by the flower necklace model, when DS < 0.26, PUL-DCSA forms the loose flower necklace model. Moreover, the micellar structure of PUL-DCSA characterized by SAXS and fluorescence was different from that of the PUL-bearing shorter alkyl (octenyl or nonenyl) chains. The smaller chain stiffness qFN and larger number of monomer (glucose residues) per unit flower micelle N0u of PUL-DCSA, mainly due to the difference in the different hydrophobic alkyl side chains. This research will provide a theoretical guidance for designing biomedical materials with appropriate scale and characteristic functions in drug delivery system.

Molecular transformation of heavy oil during slurry phase hydrocracking process: influences of operational conditions

The influences of reaction temperature, duration, pressure, and catalyst concentration on the molecular transformation of residual slurry phase hydrocracking process were investigated. The molecular composition of the heteroatom compounds in the residue feedstock and its upgrading products were characterized using high-resolution Orbitrap mass spectrometry coupled with multiple ionization methods. The simultaneous promotion of cracking and hydrogenation reactions was observed with increasing of the reaction temperature and time. Specifically, there was a significant increase in the cracking degree of alkyl side chain, while the removal of low-condensation sulfur compounds such as sulfides and benzothiophenes was enhanced. In particular, the cracking reactions were more significantly facilitated by high temperatures, while an appropriately extended reaction time can result in the complete elimination of the aforementioned sulfur compounds with a lower degree of condensation. Under conditions of low hydrogen pressure and catalyst concentration, the products still exhibit a high relative abundance of easily convertible compounds such as sulfoxides, indicating a significant deficiency in the effectiveness of hydrogenation. The hydrogen pressure exhibits an optimal value, beyond which further increments have no effect on the composition and performance of the liquid product but can increase the yield of the liquid product. At significantly high catalyst concentration, the effect of desulfurization and deoxidation slightly diminishes, while the aromatic saturation of highly condensed compounds was notably enhanced. This hydrogenation saturation effect cannot be attained through manipulation of other operational parameters, thereby potentially benefiting subsequent product processing and utilization. This present study demonstrates a profound comprehension of the molecular-level residue slurry phase hydrocracking process, offering not only specific guide for process design and optimization but also valuable fundamental data for constructing reaction models at the molecular level.

Ionic Liquid-Based Extraction Strategy for the Efficient and Selective Recovery of Scandium.

The recovery of scandium (Sc) from highly acidic industrial effluents is currently hindered by the use of large quantities of flammable and toxic organic solvents. This study developed an extraction system using ionic liquids (ILs) and phenylphosphinic acid (PPAH) as diluents and an extractant, respectively, to selectively recover Sc from the aqueous phase. The effect of IL chemical structure, aqueous pH and temperature on the extraction of Sc was systematically investigated and the findings revealed that ILs with longer alkyl side chains had reduced Sc extraction ability due to the presence of continuous nonpolar domains formed by the self-aggregation of the IL alkyl side chain. The IL/PPAH system maintained high extraction ability toward Sc across a wide temperature range (288 K to 318 K) and the extraction efficiency of Sc could be improved significantly by increasing the aqueous pH. The extraction process involved proton exchange, resulting in the formation of a metal-ligand complex (Sc(PPA)3).

Impact of the alkyl side-chain length on solubility, interchain packing, and charge-transport properties of amorphous π-conjugated polymers

Increasing the length of alkyl side chains is a typical way to improve the solubility of π-conjugated polymers designed for use in solution-processed devices. However, these modifications have also been reported to alter the film morphology. Given that the mechanism leading to improved solubility is not well documented yet and the nanoscale (local) morphologies of amorphous π-conjugated polymer films are difficult to characterize experimentally, here, we combine molecular dynamics simulations and long-range corrected density functional theory calculations to examine at the molecular scale the impact that the alkyl side-chain length has on polymer solubility and film morphologies. As a representative example, we consider poly(thieno[3,4-c]pyrrole-4,6-dione-alt-3,4-difluorothiophene) (PTPD[2F]T) with two different lengths of the alkyl side chains on the thieno[3,4-c]pyrrole-4,6-dione (TPD) moieties, i.e., 2-hexyldecyl (2HD) and 2-decyltetradecyl (2DT). A detailed analysis of polymer–solvent and polymer–polymer interactions provides a picture that describes the underlying mechanism for improved solubility in going from 2HD to 2DT. We then underline an intrinsic characteristic that decreasing the side-chain length brings a greater extent of backbone planarity and lesser side chain-TPD interactions, which leads to higher interchain π-π packing density and order, while the interchain π-π packing patterns remain similar in the two films. These morphologies are discussed in terms of the charge-transport properties between neighboring PTPD[2F]T chains, which point to a higher electron mobility in the PTPD[2F]T films with shorter alkyl side chains. Overall, our findings offer guidance in the field of solution-processed electronic devices by pointing out that the polymer alkyl side-chain length could be minimized to improve carrier mobility while ensuring polymer solubility.