Control of Wetting Behavior Using Post-Polymerization Modifications of Surface Chemical Functionality

Abstract

Modification of surface chemical functionality of a variety of materials using the reactions of readily accessible diarylcarbenes permits the control of wetting behavior. When coupled with an additional chemical derivatization step, a wider range of surface polarity becomes available.

Antibacterial Drug Releasing Materials by Post-Polymerization Surface Modification

“…9,14,34 Bioassay method 8 : Samples of modi¯ed beads (30 mg) were mixed with 90 mg of blank beads to give a four-fold dilution. Six sets of beads (10 mg each) were prepared for the hole-plate bioassay; of these six sets, three sets were used for S.aureus plates as triplicate, and three sets were for testing with E.coli plates in triplicate.…”

“…has been reported (but also see ESI for relevant data) 9,14,34 Reaction of this modi¯ed polymer with the known iodides 5a,b 28,35 then gave the spirocyanine materials 6a,b. The presence of the spiropyran unit on the surface was con¯rmed from the presence of nitro groups in the ATR-IR spectrum of 6a (1510 cm À1 ), and bromo groups in the combustion analysis and XPS spectrum of 6b (see ESI); estimation of the surface loading data from the combustion analysis gave densities of 6:7 Â 10 12 , 5:0 Â 10 12 , 2:7 Â 10 12 and 2:6 Â 10 12 molecules.…”

“…In one approach, by exploiting the well-known reactivity of carbenes with both and chemical bonds for insertion and addition processes respectively, the functionalization of both reactive (organic and inorganic polymers) and inert (diamond, nanotubes, hydrocarbon polymers) materials using diaryldiazomethanes 1 to introduce varied surface properties, [2][3][4] including chromophoric, 5 protein a±nity, 6,7 biocidal, 8 chelation, 9 biocompatibility, 10 payload delivery, 11 dispersability, 12 nano¯lling, 13 and wettability 14,15 e®ects has been achieved. Of interest, however, was whether the surface loading density which could be achieved using this approach, which was generally in the range 0.01-0.2 mmol/g, [2][3][4] was su±cient to permit the reversible binding of small molecules at a level which was both detectable and had the capacity for a therapeutic e®ect; that this might be possible which was suggested from earlier work in which the binding of hydrogen peroxide was shown to lead to bactericidal properties, a result which was considered likely to be a best case scenario, since the existence of an extensive hydrogen binding network appeared to support multiple hydrogen peroxide units per unit of introduced surface urea groups giving high overall surface loading.…”

Surface modification using crosslinking of diamine and a bis(diarylcarbene): synthesis, characterization, and antibacterial activity via binding hydrogen peroxide

“…An unexpected crosslinking between those diamines and the dicarbene intermediate was detected, giving a structurally robust surface which improved the loading of hydrogen peroxide and greatly increased the antibacterial activity of materials or surfaces. Moreover, this crosslinking expands the surface modication approach, which has already been applied in colour, 27 uorescence, 28 biocompatibility, 29 protein binding 30 and adsorption, 31 hydrophobicity, 32 and payload delivery. 33,34 2.…”

Chemical functionalization of polyethylene surfaces by plasma-assisted carbene insertion

“…An alternative direct surface modification under milder conditions by using highly reactive diarylcarbenes, generated by thermolysis or photolysis of precursor diaryldiazomethanes, [23] has been developed, and been shown to modify the macroscopic properties of material surfaces [24,25] for the introduction of a range of properties (e.g. visible [26] and fluorescent [27] chromophore, adhesion, [28,29] biocidal, [30] and hydrophobicity [31,32] effects) onto a variety of substrates.…”