Photo‐Fries Rearrangement in Polymeric Media: An Investigation on Fully Aromatic Esters Containing the Naphthyl Chromophore

Höfler, Thomas; Grießer, Thomas; Gruber, Manfred; Jakopič, Georg; Trimmel, Gregor; Kern, Wolfgang

doi:10.1002/macp.200700456

Cited by 23 publications

(17 citation statements)

References 24 publications

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“…2). As the photolysis proceeded, the absorption spectra of both initiators increased and this effect might be attributed to the Photo-Fries rearrangement of aryl esters to hydroxy ketones as first observed by Anderson and Reese in 1960 [20][21][22][23]. This photoreaction mainly yields a mixture of ortho-and para-hydroxy ketones (see Scheme 4).…”

Section: Resultsmentioning

confidence: 86%

“Mono” and “bifunctional” aromatic esterificated benzophenone photoinitiators for free radical polymerization

et al. 2014

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Aromatic esterificated benzophenone derivatives, benzoic acid 4-benzoyl-phenyl ester (BPBz) and bis-benzoic acid 4-benzoyl-phenyl ester (BisBPBz) were simply synthesized and characterized. The triplet states of the photoinitiators were determined by laser flash photolysis and phosphorescence spectroscopy. The photodecomposition of the initiators was performed by UV light; the increase in the absorption spectra was attributed to the decreasing number of ester groups which led to an increase in ketone groups according to the Photo-Fries rearrangement of aromatic esters. The photoinitiation capabilities for methyl methacrylate (MMA) polymerizations were investigated under air and nitrogen atmospheres. Esterfunctional benzophenone photoinitiators were found to be more effective than benzophenone (BP) in the presence of a co-initiator for photoinduced free radical polymerization of MMA. The kinetics of photopolymerization for different formulations which consist of multifunctional acrylates was also studied using the Real-Time Fourier Transform infrared spectroscopy (RT-FTIR) method. The film properties of these formulations were investigated after curing of films by Mini-UVCure equipment.

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Section: Resultsmentioning

confidence: 86%

“Mono” and “bifunctional” aromatic esterificated benzophenone photoinitiators for free radical polymerization

et al. 2014

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“…Section 2.3, see Figure 23). The homolytic splitting of triphenylsulphonium cations leads to a phenyl radical, which then undergoes a Fries photo-rearrangement together with the diphenylsulphonium cation radical to yield by-products such as p-und o-(Phenylthio)biphenylenes [67]. That some m-substituted products are observed can be explained by a heterolytic decomposition followed by an electrolytic aromatic substitution of the diphenylsulphonium cation radical [68].…”

Section: Lewis Acidsmentioning

confidence: 99%

Ring-Opening Polymerization—An Introductory Review

Nuyken

Pask²

2013

Polymers

359

265

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We would like to dedicate this article to P. H. Plesch, a pioneer of cationic polymerization and a mentor and friend for many of those who are now at the forefront of this field of science. He passed away 5 March 2013 at the age of 95. We will miss him. Abstract: This short, introductory review covers the still rapidly growing and industrially important field of ring opening polymerization (ROP). The review is organized according to mechanism (radical ROP (RROP), cationic ROP (CROP), anionic ROP (AROP) and ring-opening metathesis polymerization (ROMP)) rather than monomer classes. Nevertheless, the different groups of cyclic monomers are considered (olefins, ethers, thioethers, amines, lactones, thiolactones, lactams, disulfides, anhydrides, carbonates, silicones, phosphazenes and phosphonites) and the mechanisms by which they can be polymerized involving a ring-opening polymerization. Literature up to 2012 has been considered but the citations selected refer to detailed reviews and key papers, describing not only the latest developments but also the evolution of the current state of the art.

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“…Horie et al 32 examined films doped with phenylazide and found an Án D after photoirradiation of 0.0161. Kern et al 33,34 examined the photo-Fries rearrangement based on the polymer, and observed Án D 's in the range from 0.042 to 0.070. Sakurai et al 35 reported that Án D of poly(methyl methacrylate) film doped with N-acetyl--dehydroarylalanine naphthyl ester reached about 0.02.…”

Section: Calixarene Derivatives As Refractive-index-changing Materialsmentioning

confidence: 99%

Development of Novel Photo-Functional Materials Based on Cyclic Oligomers

Kudo

Nishikubo

2009

Polym. J.

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Novel photo-functional materials, such as refractive-index-changing materials, argon fluoride (ArF) resist materials, and electron beam (EB) resist materials, were designed based on the structures of calixarenes, cyclodextrin, and noria. The synthesis and refractive-index properties of calixarene derivatives containing photo-reactive groups, including azobenzene, norbornadiene, anthracene, cinnamate, and chalcone, were examined, and refractive-index changes (Án D 's) of between 0.007 and 0.061 were observed. The synthesis and patterning properties of a single-layer ArF photoresist system of -CD derivative containing t-butyl ester and fluorine were examined, and a well-resolved 100 nm line and space pattern was obtained on a silicon wafer. A new ladder-like macrocycle, noria (water wheel in Latin), was also synthesized and its application as an EB resist material was examined. The noria derivatives noria-COO t Bu containing t-butyl ester groups, noria-BOC containing t-butyloxycarbonyl group, and noria-acetal containing acetal groups had good physical properties and photo-reactivity. EBresist based on noria-COO t Bu and noria-BOC provided clear line and space patterns at a resolution of 70 and 50 nm, respectively.The development of novel photo-functional materials has contributed substantially to progress in the electronic and optoelectronic industries. Photo-reactive groups, such as radical-or cation-polymerizable groups, photo-isomerizable groups, and photo-removable groups, are useful for obtaining ultraviolet (UV)-cured resins, refractive-index-changing materials, and photo-resist materials, respectively. The physical properties of photo-functional materials, such as film-forming characteristics, thermal stability, mechanical properties, and photo-reactivity, depend primarily on the polymer or oligomer structure. Generally, the photochemical reactivity increases with decreasing glass transition temperature (T g ), due to increase of the molecular motion of polymer chains and functional groups.The photo-chemical reactivity of oligomers is usually greater than that of polymers, due to the lower T g of oligomers compared with polymers. However, the mechanical properties, thermal stability and film-forming properties of oligomer derivatives are inferior to those of polymer derivatives. However, if a linear oligomer is changed to a cyclic oligomer by coupling reaction of the two ends, the physical properties of the resulting cyclic oligomer are expected to be superior to those of the linear oligomer. Therefore, we considered that photofunctional cyclic oligomers might combine the advantages of photo-functional polymers and photo-functional oligomers. That is, photo-functional cyclic oligomers might have both high photo-chemical reactivity and good physical properties.Calixarenes are typical cyclic oligomers containing many hydroxyl groups, and are prepared easily by the reaction of phenols with aldehydes (Scheme 1). 1Although it is well known that calixarenes are attractive materials for use as host molecules in th...

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Photo‐Fries Rearrangement in Polymeric Media: An Investigation on Fully Aromatic Esters Containing the Naphthyl Chromophore

Cited by 23 publications

References 24 publications

“Mono” and “bifunctional” aromatic esterificated benzophenone photoinitiators for free radical polymerization

“Mono” and “bifunctional” aromatic esterificated benzophenone photoinitiators for free radical polymerization

Ring-Opening Polymerization—An Introductory Review

Development of Novel Photo-Functional Materials Based on Cyclic Oligomers

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