Polymeric Photosensitizers, 5. Synthesis and Photochemical Properties of Poly[(N-isopropylacrylamide)-co-(vinylbenzyl chloride)] Containing Covalently Bound Rose Bengal Chromophores

Nowakowska, Maria; pczyński, Mariusz K; browska, Monika D

doi:10.1002/1521-3935(20010601)202:9<1679::aid-macp1679>3.0.co;2-r

Cited by 23 publications

(11 citation statements)

References 28 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…5 ). Rose Bengal (RB) is characterized by a very bright pink color and halochromic transition from pink to orange at low pH values 66 – 68 . Another important family of pH-responsive dyes are based on the sulfonphthaleine structure, which are known for their good water solubility and tunable pKa through substituent selection, allowing the fine tuning of the pKa between 4.8 and 9.1 69 .…”

Section: Resultsmentioning

confidence: 99%

Plasma dye coating as straightforward and widely applicable procedure for dye immobilization on polymeric materials

et al. 2018

View full text Add to dashboard Cite

Here, we introduce a novel concept for the fabrication of colored materials with significantly reduced dye leaching through covalent immobilization of the desired dye using plasma-generated surface radicals. This plasma dye coating (PDC) procedure immobilizes a pre-adsorbed layer of a dye functionalized with a radical sensitive group on the surface through radical addition caused by a short plasma treatment. The non-specific nature of the plasma-generated surface radicals allows for a wide variety of dyes including azobenzenes and sulfonphthaleins, functionalized with radical sensitive groups to avoid significant dye degradation, to be combined with various materials including PP, PE, PA6, cellulose, and PTFE. The wide applicability, low consumption of dye, relatively short procedure time, and the possibility of continuous PDC using an atmospheric plasma reactor make this procedure economically interesting for various applications ranging from simple coloring of a material to the fabrication of chromic sensor fabrics as demonstrated by preparing a range of halochromic materials.

show abstract

Section: Resultsmentioning

confidence: 99%

Plasma dye coating as straightforward and widely applicable procedure for dye immobilization on polymeric materials

et al. 2018

View full text Add to dashboard Cite

show abstract

“…Polymer materials are also good candidates for immobilizing photosensitizing dyes . Polymer substrates embedding photosensitizers include hydrophilic, − hydrophobic, , amphiphilic, − or microporous polymers and polymer beads. , …”

Section: Introductionmentioning

confidence: 99%

Photoactive, Porous Honeycomb Films Prepared from Rose Bengal-Grafted Polystyrene

et al. 2013

View full text Add to dashboard Cite

Honeycomb-structured porous polymer films based on photosensitizer-grafted polystyrene are prepared through the breath figure process. Rose Bengal (RB) photosensitizer is first attached to a well-defined poly(styrene-stat-4-vinylbenzyl chloride) statistical copolymer, synthesized by nitroxide-mediated radical polymerization. The RB grafted poly(styrene-stat-4-vinylbenzyl chloride) (ca. 20,000 g mol(-1) molar mass, 1.2 dispersity) leads to porous polymer films, with a hexagonal pore pattern, while a simple mixture of poly(styrene-stat-4-vinylbenzyl chloride) and the insoluble RB photosensitizer produced unstructured, nonporous films. The RB-grafted honeycomb films, compared with the corresponding nonporous flat films, are more efficient for oxidation of organic molecules via singlet oxygen production at a liquid/solid interface. The oxidations of 1,5-dihydroxynaphthalene to juglone and α-terpinene to ascaridole are followed in ethanol in the presence of both types of films. Oxidation of the organic molecules is a factor 5 greater with honeycomb compared to the nonporous films. This gain is ascribed to two factors: the specific location of the polar photosensitizer at the film interface and the greater exchange surface, as revealed by fluorescence and scanning electron microscopies.

show abstract

“…Application of immobilized PSs exhibits several obvious advantages over their use in solution: immobilized PSs can be used in solvents in which free PSs are insoluble, they can be easily removed at the end of the treatment, can be reused, can be introduced into continuous processes , and are more resistant to bleaching by light and oxygen than free PSs . There are a number of methods for solid phase immobilization of PSs—adsorption onto a solid support, formation of ionic bonds between the PS and ion‐exchange resins, formation of a covalent bond between the PS and a polymer support and incorporation of the PS into a polymeric film . Most of the studies in the field concentrate on a search for effective methods for covalent attachment of the PS molecules to solid supports.…”

Section: Introductionmentioning

confidence: 99%

“…Most of the studies in the field concentrate on a search for effective methods for covalent attachment of the PS molecules to solid supports. Covalent attachment of a large number of PSs, such as Rose Bengal (RB), eosin, fluorescein, chlorophyllin, hematoporphyrin and Zn(II) phthalocyanine tetrasulfonic acid to various supports, including silica gel, poly(styrene‐co‐vinylbenzyl chloride), poly[( N ‐isopropylacrylamide)‐co‐(vinylbenzyl chloride)], poly[(sodium p ‐styrenesulfonate)‐co‐(4‐vinylbenzyl chloride)] and chitosan has been reported . PSs that were covalently attached to polymers demonstrated high (up to 0.91) quantum yields of singlet oxygen formation .…”

Section: Introductionmentioning

confidence: 99%

Eradication of Gram‐Positive and Gram‐Negative Bacteria by Photosensitizers Immobilized in Polystyrene

Nakonechny

Pinkus

Hai

et al. 2012

Photochem & Photobiology

View full text Add to dashboard Cite

Immobilization of photosensitizers in polymers opens prospects for their continuous and reusable application. Methylene blue (MB) and Rose Bengal were immobilized in polystyrene by mixing solutions of the photosensitizers in chloroform with a polymer solution, followed by air evaporation of the solvent. This procedure yielded 15-140 μm polymer films with a porous surface structure. The method chosen for immobilization ensured 99% enclosure of the photosensitizer in the polymer. The antimicrobial activity of the immobilized photosensitizers was tested against Gram-positive and Gram-negative bacteria. It was found that both immobilized photosensitizers exhibited high antimicrobial properties, and caused by a 1.5-3 log10 reduction in the bacterial concentrations to their total eradication. The bactericidal effect of the immobilized photosensitizers depended on the cell concentration and on the illumination conditions. Scanning electron microscopy was used to prove that immobilized photosensitizers excited by white light caused irreversible damage to microbial cells. Photosensitizers immobilized on a solid phase can be applied for continuous disinfection of wastewater bacteria.

show abstract

Polymeric Photosensitizers, 5. Synthesis and Photochemical Properties of Poly[(N-isopropylacrylamide)-co-(vinylbenzyl chloride)] Containing Covalently Bound Rose Bengal Chromophores

Cited by 23 publications

References 28 publications

Plasma dye coating as straightforward and widely applicable procedure for dye immobilization on polymeric materials

Plasma dye coating as straightforward and widely applicable procedure for dye immobilization on polymeric materials

Photoactive, Porous Honeycomb Films Prepared from Rose Bengal-Grafted Polystyrene

Eradication of Gram‐Positive and Gram‐Negative Bacteria by Photosensitizers Immobilized in Polystyrene

Contact Info

Product

Resources

About