Photoreactions of o-quinones with olefins: a new type of reaction leading to dioxole derivatives

Farid, Samir; Heß, Dieter; Pfundt, G.; Scholz, K.-H.; Steffan, G.

doi:10.1039/c19680000638

Cited by 10 publications

(8 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Upon light exposure, PQ in its excited state reacts with the MMA monomer. Four different routes (I, II, III, and IV; Figure 5) are available for photoreactions between one PQ molecule and one MMA molecule 3, 19, 20. The Figure 5 show that during light exposure of the photopolymer material the o‐quinones on the PQ molecules may bond to the olefins on the MMA molecules.…”

Section: Resultsmentioning

confidence: 99%

Nitroanilines enhancing the holographic data storage characteristics of the 9,10‐phenanthrenequinone‐doped poly(methyl methacrylate) photopolymer

Hsiao

Lin

et al. 2012

J of Applied Polymer Sci

View full text Add to dashboard Cite

This article describes an approach toward improving the characteristics of a photopolymer for holographic data storage application. The maximum diffraction efficiency (g max ) and dynamic range (M#) of 9,10-phenanthrenequinone (PQ)-doped poly (methyl methacrylate; PMMA) both improved significantly after co-doping with one of three nitroanilines-N,N-dimethyl-4-nitroaniline (DMNA), N-methyl-4-nitroaniline (MNA), and 4-nitroaniline (pNA). In particular, the value of g max increased from 38% for the PMMA/PQ system to 72% for the PMMA/PQ/DMNA system (a 1.89-fold improvement) and the value of M# increased accordingly from 2.7 to 7.3 (a 2.70-fold improvement). Thus, the holographic data storage characteristics of PMMA/PQ photopolymers can be improved through co-doping with nitroaniline compounds. We also investigated the mechanism of the nitroaniline-induced improvement in optical storage performance using proton nuclear magnetic resonance and X-ray photoelectron spectroscopy.

show abstract

Section: Resultsmentioning

confidence: 99%

Nitroanilines enhancing the holographic data storage characteristics of the 9,10‐phenanthrenequinone‐doped poly(methyl methacrylate) photopolymer

Hsiao

Lin

et al. 2012

J of Applied Polymer Sci

View full text Add to dashboard Cite

show abstract

“…14 In addition, characteristics of photo-and thermo-reactions of PQ molecules with olefin-based molecules have been studied. 15 The results show that during light exposure of the photopolymer material the o-quinones on the PQ molecules may bond to the olefins on the MMA molecules. Under photo-and/or thermo-reactions, four different routes might be taken in the form of one PQ molecule to one MMA molecule bonding structure, as shown in Fig.…”

Section: Introductionmentioning

confidence: 91%

Analyses on physical mechanism of holographic recording in phenanthrenequinone-doped poly(methyl methacrylate) hybrid materials

2004

View full text Add to dashboard Cite

The photoproducts in phenanthrenequinone (PQ)-dissolved methyl methacrylate (MMA) liquid samples and PQ-doped poly(methyl methacrylate) (PQ/PMMA) solid photopolymer samples have been analyzed by various chemical measurements. A mechanism for holographic recording in our PQ/PMMA photopolymer is proposed. By UV-VIS transmission and photoluminescence spectral measurements, we find that under light exposure the molecular structure of PQ is transformed to be less conjugated. The measured results of mass spectra, Fourier transform infrared spectra, NMR spectra, and gel permeation chromatograph analyses provide some evidence for recognizing the molecular structure of the photoproducts in our PQ/PMMA photopolymers. The results show that under light exposure the PQ and MMA form new molecules, mainly an adduct of one PQ molecule with one MMA molecule. In addition, PQ also reacts as a photoinitiator to form PMMA oligomers in our samples. The structure change of the PQ molecule induces a strong change of the refractive index in the material. It provides a mechanism to record a phase hologram in our PQ/PMMA photopolymer. Holographic recordings in the samples are demonstrated, and the dynamic range of the sample is investigated.

show abstract

“…A comparison of the recording behavior has been made between PQ:PMMA photopolymers fabricated by diverse conditions 8 that under light exposure PQ molecules might attach on the PMMA polymer chain, combine with single MMA molecule or induce photo-polymerization of MMA molecules. On the other hand, investigation on photo-and thermo-reactions of PQ molecules with olefin-based molecules in PQ/MMA mixtures showed that four different compounds could be produced 9 . The four possible routes are named as I, II, III, and IV, shown in the Fig.…”

Section: Introductionmentioning

confidence: 99%

Doped PMMA photopolymer for volume holographic recording

Lin

2003

SPIE Proceedings

View full text Add to dashboard Cite

In this paper, we report investigations on chemical analyses and optical measurements of our PQ doped PMMA photopolymer material. We have analyzed chemical compositions of four different samples: PQ doped PMMA solid and PQ dissolved MMA liquid samples, with light exposed and unexposed conditions, respectively. The investigations provide us a good understanding about the photochemical behaviors of the PQ and the MMA molecules during optical recording. Then, a mechanism for holographic recording is proposed. This result has been applied to develop photopolymers doped with different dye molecules. With changing of dye molecules, we have made three new PMMA-based photopolymers. Their holographic recording characteristics have been tested and discussed.

show abstract

Photoreactions of o-quinones with olefins: a new type of reaction leading to dioxole derivatives

Cited by 10 publications

References 0 publications

Nitroanilines enhancing the holographic data storage characteristics of the 9,10‐phenanthrenequinone‐doped poly(methyl methacrylate) photopolymer

Nitroanilines enhancing the holographic data storage characteristics of the 9,10‐phenanthrenequinone‐doped poly(methyl methacrylate) photopolymer

Analyses on physical mechanism of holographic recording in phenanthrenequinone-doped poly(methyl methacrylate) hybrid materials

Doped PMMA photopolymer for volume holographic recording

Contact Info

Product

Resources

About