Photochemical C–H oxygenation of side-chain methyl groups in polypropylene with chlorine dioxide

Ohkubo, Kei; Asahara, Haruyasu; Inoue, Tsuyoshi

doi:10.1039/c9cc01037h

Cited by 22 publications

(24 citation statements)

References 27 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…A glassware system reported previously was used to perform the oxidation of a PP NWF in a large size and/or under heating conditions. 18,19 An aqueous solution of NaClO2 was added to the outer moat of the glassware, while the sample was placed on the inner side. During the reaction, the sample was protected from direct UV irradiation using aluminum sheet.…”

Section: Methodsmentioning

confidence: 99%

“…17 This photo-activated ClO2 • oxidation method is applicable for oxidative surface modification of polymer materials, including chemically inactive PP. 18,19 Furthermore, this surface modification method can be applied to complex structures because the activated gas can react inside the textile. 20 In this study, the surface of PP NWFs was oxidized via a modification method using photo-activated ClO2 • gas.…”

mentioning

confidence: 99%

See 1 more Smart Citation

Surface Functionalization of Polypropylene Nonwoven Fabric for Introducing Repeatable Controlled Drug Release Property

Yamamoto

Asahara

Moriguchi

et al. 2022

Preprint

Self Cite

View full text Add to dashboard Cite

We developed polypropylene nonwoven fabrics (PP NWFs) with controlled drug release property via surface modification using the photo-activated chlorine dioxide radical (ClO2•) oxidation method, followed by β-cyclodextrin (CD) loading. PP materials are challenging to functionalize for allowing the immobilization of drugs, owing to their low reactivity and surface energy. Our β-CD/PP NWFs composite showed sustained drug release behavior over 12 h in phosphate buffer, indicating that β-CDs supported on PP fibers functioned successfully. Our functionalization method is desirable for drug delivery in medicinal chemistry.

show abstract

Section: Methodsmentioning

confidence: 99%

mentioning

confidence: 99%

Surface Functionalization of Polypropylene Nonwoven Fabric for Introducing Repeatable Controlled Drug Release Property

Yamamoto

Asahara

Moriguchi

et al. 2022

Preprint

Self Cite

View full text Add to dashboard Cite

show abstract

“…ClO 2 . can also act as an efficient oxidant for the oxygenation of CH 3 ‐moieties on the PP surface, which is the first convenient chemical procedure for the C−H bond oxygenation of surface of PP and PE as olefinic plastics, without using heavy metal oxides . The surfaces of the oxygenated polymer can be further transformed into various organic compounds through the reaction with carboxylic acids on the surface, which can have a significant impact in synthetic polymer chemistry.…”

Section: Metal‐free Photocatalystsmentioning

confidence: 99%

Photoinduced Generation of Superoxidants for the Oxidation of Substrates with High C−H Bond Dissociation Energies

et al. 2019

View full text Add to dashboard Cite

Oxidation of substrates, such as methane, with large C−H bond dissociation energies usually requires harsh reaction conditions, such as high temperature and pressure. The use of photoexcited states of oxidants enables the oxidation of substrates which would otherwise be unable to react thermally. This Review focuses on photoinduced generation of strong inorganic and organic oxidants, which enables the oxidation of substrates with strong C−H bonds. For example, photoexcitation of a CeIV‐alkoxide complex results in the cleavage of Ce−O bond to produce an alkoxyl radical, which can abstract a hydrogen atom from methane to afford a methyl radical, leading to amination of methane with tert‐butyloxycarbonyl (Boc)‐protected monomethylhydrazine. Hydrogen atom abstraction from alkanes also occurs induced by the photoexcited state of tetrabutylammonium decatungstate, leading to alkylations and acylation of both aromatic and aliphatic N‐tosylimines. Photoexcitation of Bi‐ and V‐containing beta zeolites also results in hydrogen atom abstraction from methane to produce methanol at ambient temperature. The photoexcited state of a manganese(IV)‐oxo complex binding with two Sc3+ ions has a surprisingly long lifetime (6.4 μs), and is able to oxidize benzene to produce phenol. Chlorine radicals, that can be generated by photoinduced oxidation of chloride ion by the photoexcited states of oxidants or by photoexcitation of a chlorine dioxide radical, abstracts a hydrogen atom from alkanes including methane to produce alkyl radicals, which can be converted to the oxygenated products. Photoinduced oxidation of methane was also made possible by mixing photosystem II (PSII) and the membrane fraction of a particular form of methane monooxygenase. A PSII model reaction has been achieved by using p‐benzoquinone derivatives as plastoquinone analogues with a non‐heme FeII catalyst in the presence of H2O under photoirradiation, to yield dioxygen with the corresponding hydroquinone derivatives.

show abstract

“…[1][2][3] This main disadvantage is attributed that PP has no dyeing site owing to the simple molecular structure. Various methods for dyeing of PP fibers have been studied and performed so far, for examples, spin-dyeing, 4 mixing of a good-dyeing resin, [5][6][7] surface modification method, 8 and supercritical fluid method. 9 Nevertheless some problems have been still remained, i.e.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Blue Dyeing Ability for Polypropylene Fabrics of Various 3,7-Bis(dialkylamino)phenoxazin-5-ium Salts and the Sulfur and Selenium Analogs

Segi¹,

Yoshida²

2021

HETEROCYCLES

View full text Add to dashboard Cite

Bis(dialkylamino)phenoxazin-5-ium salts having different amino groups (dimethylamino, diethylamino, dipropylamino, dibutylamino, and pyrrolidyl) and counter anions (chloride, bromide, iodide, hydrogensulfate, and nitrate) were synthesized in up to 80% isolated yield as blue cationic dyes. In a d d i t i o n , 3 , 7 -b i s ( d i e t h y l a m i n o ) p h e n o t h i a z i n -5 -i u m a n d 3 , 7bis(diethylamino)phenoselenazin-5-ium iodides were also synthesized in 20% and 17% isolated yields, respectively. Polypropylene fabrics were dyed with the above synthesized blue cationic dyes. As an evaluation result, it has been found that the moderate size such as diethylamino groups at the 3 and 7 positions of phenoxazinium salts is suitable for the dyeing ability.

show abstract

Photochemical C–H oxygenation of side-chain methyl groups in polypropylene with chlorine dioxide

Abstract: The chlorine dioxide radical (ClO2˙) was found to act as an efficient oxidizing agent for the aerobic C–H oxygenation of the side-chain methyl groups in polypropylene under photoirradiation.

Cited by 22 publications

References 27 publications

Surface Functionalization of Polypropylene Nonwoven Fabric for Introducing Repeatable Controlled Drug Release Property

Surface Functionalization of Polypropylene Nonwoven Fabric for Introducing Repeatable Controlled Drug Release Property

Photoinduced Generation of Superoxidants for the Oxidation of Substrates with High C−H Bond Dissociation Energies

Synthesis and Blue Dyeing Ability for Polypropylene Fabrics of Various 3,7-Bis(dialkylamino)phenoxazin-5-ium Salts and the Sulfur and Selenium Analogs

Contact Info

Product

Resources

About