Synthesis and photochemical property of polymers with pendant donor–acceptor‐type norbornadiene moieties

Kawashima, Naoyuki; Kameyama, Atsushi; Nishikubo, Tadatomi; Nagai, Takabumi

doi:10.1002/pola.1154

Cited by 15 publications

(13 citation statements)

References 27 publications

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“…In addition to conversion and storage of solar energy, the photochemical isomerization of NBD has been studied as a new alternative in the field of optoelectronics (memory, optical switches and other devices), as a photochromic system with potential application in the data storage technology, and as an energetic binder for solid rocket propellants . NBD structures are generally introduced into polymer chains as pendant moieties by postpolymerization chemical modification, by radical or cationic polymerizations of NBD‐containing vinyl monomers, or by ring‐opening copolymerization of glycidyl esters containing NBD moieties with various carboxylic anhydrides . Besides, the synthesis of polyamides containing NBD structure in the backbone by direct or catalyst transfer polycondensation has been reported earlier …”

Section: Introductionmentioning

confidence: 99%

Photoresponsive polyamides containing pentamethylated norbornadiene moieties: Synthesis and photochemical properties under sunlight irradiation

Oueslati

Abdelhedi

Merçier

et al. 2013

J. Polym. Sci. Part A: Polym. Chem.

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Photoresponsive polyamides containing main‐chain pentamethylated norbornadiene (NBD) moieties are obtained in quantitative yields via the Yamazaki–Higashi reaction between a pentamethylated NBD dicarboxylic acid and a series of aromatic diamines. Chemical structures are confirmed by 1H and 13C NMR and weight average molar masses measured by SEC are in the range of 21,500–28,600 g mol−1 with chain dispersities close to 2. Physical properties are investigated by FTIR, differential scanning calorimetry (DSC), thermogravimetric analysis, and viscosimetry. All obtained polyamides are amorphous with glass transition temperatures ranging from 68 to 124 °C. They are soluble at room temperature in common organic solvents and exhibit good thermal stabilities with Td10 values ranging from 175 to 276 °C. The photochemical isomerization of the NBD moiety into quadricyclane (QC) is studied by UV/vis spectroscopy after sunlight irradiation of polymer films. For all polyamides, a first‐order kinetic rate is observed for the conversion of NBD to QC. The thermal release of the stored energy associated to the reverse transformation of QC groups into NBD ones is about 90–95 kJ mol−1 as measured by DSC of the irradiated polymer films. © 2013 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2013, 51, 4650–4656

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Section: Introductionmentioning

confidence: 99%

Photoresponsive polyamides containing pentamethylated norbornadiene moieties: Synthesis and photochemical properties under sunlight irradiation

Oueslati

Abdelhedi

Merçier

et al. 2013

J. Polym. Sci. Part A: Polym. Chem.

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“…The introduction of NBD groups into the polymer chains as a side groups were performed either by chemical polymer modification,14–18 by cationic polymerization of NBD containing vinylic monomers,19 or by ring‐opening copolymerization of glycidyl esters containing NBD moieties with carboxylic anhydrides 20…”

Section: Introductionmentioning

confidence: 99%

Synthesis and photochemical properties of novel pentamethylated norbornadiene containing polyimides

Oueslati

Romdhane

Martin

et al. 2011

J. Polym. Sci. A Polym. Chem.

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A novel pentamethylated norbornadiene (NBD) based dianhydride, α,α′‐bis‐(3,4,5,6,7‐pentamethylcyclopenta‐2,4‐dienyl)meta‐xylene‐1,2‐dianhydride (3), was prepared from α,α′‐bis‐(pentamethylcyclopentadienyl)meta‐xylene (1) and acetylene dicarboxylic acid. The bis‐adduct formed via Diels–Alder reaction afforded tetra‐acid (2), which was chemically cyclodehydrated to lead the targeted dianhydride (3). New polyimides containing NBD moieties in the main chain were prepared from the dianhydride monomer (3) and various aromatic diamines. The chemical structure of the polymers was confirmed by both 1H and 13C NMR analysis. Their Molecular weights were also measured by SEC. All of these polyimides are soluble at room temperature in common organic solvents, such as chloroform, dichloromethane, THF, DMSO, DMF, and NMP, and show good thermal stabilities. The photochemical isomerization of the NBD into quadricyclane (QC) was investigated by UV/vis spectrophotometry from polymer films using visible sunlight as irradiation source. It was found that the kinetic rate of the conversion NBD‐QC which proceeded smoothly is a first kinetic order. The stored energies released by the transformation of QC groups into NBD ones of the irradiated polymer films were also evaluated by DSC measurement and were found to be around 90 kJ mol−1. © 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2011

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“…[10][11][12][13] Nishikubo et al [14][15][16][17] reported that polymers containing certain norbornadiene (NBD) moieties in the main and side chains showed high photochemical reactivity, and had a high photo-energy storage capability. NBD is converted to quadricyclane (QC) under UV irradiation, and the resulting polymers are expected to be good photo-energy transformation systems.…”

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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Synthesis and photochemical property of polymers with pendant donor–acceptor‐type norbornadiene moieties

Cited by 15 publications

References 27 publications

Photoresponsive polyamides containing pentamethylated norbornadiene moieties: Synthesis and photochemical properties under sunlight irradiation

Photoresponsive polyamides containing pentamethylated norbornadiene moieties: Synthesis and photochemical properties under sunlight irradiation

Synthesis and photochemical properties of novel pentamethylated norbornadiene containing polyimides

Development of Novel Photo-Functional Materials Based on Cyclic Oligomers

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