Molecular Size Effects of Diarylnitrone Additive on the Refractive-Index Change in Poly(methyl methacrylate) Film

Tanaka, Kenta; Fukuda, Mariko; Igarashi, Tetsutaro; Sakurai, Tadamitsu

doi:10.1295/polymj.37.776

Cited by 7 publications

(7 citation statements)

References 8 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…From analysis of the molecular size effects of diarylnitrone additive on the refractive index change in PMMA film, it was found that the magnitude of Dn has a clear tendency to increase as the maximum wavelength of the first absorption band in a given additive is shifted to longer wavelengths. 17 As PMMA film doped with (Z)-1 showed no absorption in the 450-700 nm region, it is anticipated on the basis of this finding that the 1d-f-derived oxazolone derivative 2b exhibits its absorption at longer wavelengths than does the 1a-c-derived oxazolone 2a and, hence, (Z)-1d-f give larger Dn values than (Z)-1a-c. The results obtained are compatible with our prediction, shedding much light on the application to new optical materials.…”

Section: Resultsmentioning

confidence: 85%

“…17 Because this finding provides a good criterion for designing better optical materials, it is significant to generalize this correlation so as to be applicable to polymer films, the refractive indices of which are enhanced by the photochemical transformation of dopants. To confirm whether the above-mentioned correlation is applicable to other systems and then to obtain information for developing a new type of optical material, we synthesized (Z)-Nacyl-a-dehydroarylalanine naphthyl ester derivatives (Z)-1a-f (Scheme 1) and investigated aryl substituent effects on the refractive index change of PMMA films caused by the photochemical transformation of these naphthyl esters as dopants.…”

Section: Introductionmentioning

confidence: 99%

“…[1][2][3] Recently, much attention has been devoted to the photochemical control of refractive indices for polymer films, owing to their potential in optical network technology. 3 Although there are extensive studies directed toward a photoinduced decrease in refractive indices for polymer films, [4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19] only a few attempts have been made to enhance the refractive index through photochemical transformations. 12,[20][21][22][23][24][25] For example, Langer et al 21 reported that irradiation of a polymerbearing thiocyanate pendants enhanced the refractive index (n) of the polymer by 0.031.…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Effects of aryl substituents in N-acetyl-α-dehydroarylalanine naphthyl ester additive on the photoinduced refractive index change of poly(methyl methacrylate) film

Nakajima

Komatsu

Iikura

et al. 2010

Polym J

Self Cite

View full text Add to dashboard Cite

Aryl substituent effects on photoinduced refractive index changes were investigated with the use of poly(methyl methacrylate) (PMMA) films doped with (Z)-N-acetyl-a-dehydroarylalanine naphthyl esters ((Z)-1). Upon irradiation with Pyrex-filtered or unfiltered light from a high-pressure mercury lamp, (Z)-1 underwent heterolytic cleavage of the ester C(¼O)-O bond preferentially in both solution and PMMA film to afford arylmethylene-substituted (Z) oxazolone and naphthol derivatives as major products, irrespective of the aryl substituents introduced. Irradiation of (Z)-1 in the film with the unfiltered light enabled much more rapid photochemical transformation into the oxazolones and the intense ultraviolet absorption shifted to longer wavelength relative to that of the starting naphthyl esters. Analysis of the aryl substituent effects confirmed that the PMMA/(Z)-1 system, in which 1-naphthylmethylene-substituted oxazolone was formed along with 1-naphthol, enhanced the refractive index of this polymer film by as much as 0.020.

show abstract

Section: Resultsmentioning

confidence: 85%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Effects of aryl substituents in N-acetyl-α-dehydroarylalanine naphthyl ester additive on the photoinduced refractive index change of poly(methyl methacrylate) film

Nakajima

Komatsu

Iikura

et al. 2010

Polym J

Self Cite

View full text Add to dashboard Cite

show abstract

“…Miyata et al 23 reported that 4-N,N-dimethylaminophenyl-N-phenyl nitrone doped in poly-(methyl methacrylate) films showed Án D 's of 0.026-0.028. Sakurai et al [24][25][26][27][28] found that films containing certain nitrone derivatives showed Án D 's of 0.014-0.023 upon photo-isomerization. Knol and Müllen 29,30 showed that polymers with pendant 9-substituted anthracene (AT) had large Án D 's in the range of 0.013 to 0.076 upon photo-dimerization of AT.…”

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.

View full text Add to dashboard Cite

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...

show abstract

“…[15][16][17][18][19][20] These photoreactive groups showed changes of π-electron system after photoirradiation, with decreased R values.…”

Section: Introductionmentioning

confidence: 99%

Novel Refractive Index Increase Material Based on Polystyrenes with Pendant Bicyclo Orthoester Groups upon Photoirradiation

et al. 2009

View full text Add to dashboard Cite

Molecular Size Effects of Diarylnitrone Additive on the Refractive-Index Change in Poly(methyl methacrylate) Film

Cited by 7 publications

References 8 publications

Effects of aryl substituents in N-acetyl-α-dehydroarylalanine naphthyl ester additive on the photoinduced refractive index change of poly(methyl methacrylate) film

Effects of aryl substituents in N-acetyl-α-dehydroarylalanine naphthyl ester additive on the photoinduced refractive index change of poly(methyl methacrylate) film

Development of Novel Photo-Functional Materials Based on Cyclic Oligomers

Novel Refractive Index Increase Material Based on Polystyrenes with Pendant Bicyclo Orthoester Groups upon Photoirradiation

Contact Info

Product

Resources

About