Access to thermally robust and abrasion resistant antimicrobial plastics: synthesis of UV-curable phosphonium small molecule coatings and extrudable additives

Bedard, Joseph; Caschera, Alexander; Foucher, Daniel A.

doi:10.1039/d1ra00555c

Cited by 7 publications

(3 citation statements)

References 50 publications

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“…These values are within 1 order of magnitude of those reported for other recently reported charged, contact-active antibacterial surfaces. 65,66 The wettabilities of the phosphonium coatings were assessed using WCA measurements. All surfaces were hydrophilic (WCA range: 50−62°), presumably due to the amides and charged phosphonium groups on the coatings, with the BuP surfaces being a bit more hydrophobic than the PhP surfaces.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

pH-Responsive Antibacterial Surfaces Based on Cross-Linked Phosphonium Polymers

Vásquez Peña,

Nygard,

Ragogna

et al. 2024

ACS Appl. Polym. Mater.

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Section: ■ Experimental Sectionmentioning

confidence: 99%

pH-Responsive Antibacterial Surfaces Based on Cross-Linked Phosphonium Polymers

Vásquez Peña,

Nygard,

Ragogna

et al. 2024

ACS Appl. Polym. Mater.

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“…Benzaldehyde (Acros Organics) was distilled with a dephlegmator under reduced pressure prior to use. Diphenylphosphine, , [M(COD)Cl 2 ] (M = Pd, Pt), and 2-(benzo[ d ]thiazol-2-yl)aniline (NH 2 –Pbt) were prepared as reported previously. IR spectra were recorded in KBr pellets by means of an FT-801 Fourier spectrometer (Simex).…”

Section: Experimental Sectionmentioning

confidence: 99%

Pd(II)- and Pt(II)-Assisted P–C Activation/Cyclization Reactions with a Luminescent α-Aminophosphine

Afonin,

Martynenko,

Kolybalov

et al. 2023

Inorg. Chem.

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There is unceasing interest toward transformations of phosphine derivatives, which are facilitated by transition metals. We report a facile Pd(II)-and Pt(II)-assisted P−C bond cleavage in a luminescent 2-phenylbenzothiazole-based αmethylaminophosphine (PCN, 1). Specifically, reactions between 1 and [M(COD)Cl 2 ] (M = Pd, Pt; COD = cycloocta-1,5-diene) in different solvents (methylene chloride, acetonitrile, pyridine, toluene) resulted in the formation of PPh 2 − , captured either as a bridging ligand in binuclear complexes with a {M 2 (PPh 2 ) 2 } moiety or as an adduct to COD in [Pt 2 (PPh 2 COD) 2 Cl 2 ]. The heterocyclic part transforms to annulated c-CN + species with a 1,2-dihydroquinazoline cycle formed. In the presence of pyridine as a base, annulated form c-CN + destabilizes and undergoes reverse cyclization transforming to deprotonated CN form. Quantum-chemical density functional theory (DFT) calculations predict that a crucial step in the reactions involves proton transfer from the N atom of the amino group of PCN to a neighboring molecule. A combination of high photophysical sensitivity of c-CN + toward its immediate environment and rich structural capabilities in assembling (c-CN) 2 2+ pairs in different crystal packings in a family of phases with the general formula (c-CN) 2 [M 2 (PPh 2 ) 2 Cl 4 ] allows one to fine-tune the luminescence properties of the latter. The results were rationalized as a variation of π−π intercationic spacings, which tunes the degree of excitedstate charge transfer between c-CN + cations. As a result, compounds with relatively short interplanar π−π-separation between the cations show a stronger charge-transfer-mediated bathochromic shift.

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“…It should be mentioned that phosphonium compounds have also been applied as bactericides that are covalently bonded to plastic surfaces or used as co-extrusive additives for plastic materials in goods production [ 34 ]. Such surfaces are confirmed to demonstrate antibacterial properties.…”

Section: Introductionmentioning

confidence: 99%

Sterically Hindered Quaternary Phosphonium Salts (QPSs): Antimicrobial Activity and Hemolytic and Cytotoxic Properties

Ermolaev

Arkhipova

Miluykov

et al. 2021

IJMS

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Structure–activity relationships are important for the design of biocides and sanitizers. During the spread of resistant strains of pathogenic microbes, insights into the correlation between structure and activity become especially significant. The most commonly used biocides are nitrogen-containing compounds; the phosphorus-containing ones have been studied to a lesser extent. In the present study, a broad range of sterically hindered quaternary phosphonium salts (QPSs) based on tri-tert-butylphosphine was tested for their activity against Gram-positive (Staphylococcus aureus, Bacillus сereus, Enterococcus faecalis) and Gram-negative (Escherichia coli, Pseudomonas aeruginosa) bacteria and fungi (Candida albicans, Trichophyton mentagrophytes var. gypseum). The cation structure was confirmed to determine their biological activity. A number of QPSs not only exhibit high activity against both Gram-positive and -negative bacteria but also possess antifungal properties. Additionally, the hemolytic and cytotoxic properties of QPSs were determined using blood and a normal liver cell line, respectively. The results show that tri-tert-butyl(n-dodecyl)phosphonium and tri-tert-butyl(n-tridecyl)phosphonium bromides exhibit both low cytotoxicity against normal human cells and high antimicrobial activity against bacteria, including methicillin-resistant strains S. aureus (MRSA). The mechanism of QPS action on microbes is discussed. Due to their high selectivity for pathogens, sterically hindered QPSs could serve as effective tunable biocides.

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Access to thermally robust and abrasion resistant antimicrobial plastics: synthesis of UV-curable phosphonium small molecule coatings and extrudable additives

Abstract: Thermally robust UV-curable phosphoniums can be utilized as chemically bound surface coatings or as additives in extruded plastics to create an antimicrobial shield on high contact surfaces.

Cited by 7 publications

References 50 publications

pH-Responsive Antibacterial Surfaces Based on Cross-Linked Phosphonium Polymers

pH-Responsive Antibacterial Surfaces Based on Cross-Linked Phosphonium Polymers

Pd(II)- and Pt(II)-Assisted P–C Activation/Cyclization Reactions with a Luminescent α-Aminophosphine

Sterically Hindered Quaternary Phosphonium Salts (QPSs): Antimicrobial Activity and Hemolytic and Cytotoxic Properties

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