Preparation of Diarylethene Substituted Polymer Films for Optical Recording
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Preparation of Diarylethene Substituted Polymer Films for Optical Recording Song Yun Cho and Eunkyoung Kim Advanced Materials Division, Korea Research Institute of Chemical Technology, P.O. Box 107, Yusong, Taejon, South Korea ABSTRACT Effect of photo-irradiation on the color change of diarylethene polymer films was investigated. Diarylethene polymer films were prepared from photopolymerization of a radical curable mixture of diarylethene compound and a fluoroalkylacrylate containing a photo initiator. 1-[6'-(Methacryloxyethyloxycarbonyl)-2'-methylbenzo[b]thiophene-3'-yl]-2(2"-methylbenzo[b]thiophene-3"-yl)hexafluorocyclopentene (MMBTF6)
was synthesized
from 2,3-bis(2-methylbenzo[b]thiophene-3-yl)hexafluorocyclopentene (BTF6) in three steps. 2,2,3,3-Tetrafluoro-1,4-butyldiacrylate (TFBDA) was synthesized from the corresponding diol and acryloyl chloride in the presence of a base. The photocurable mixture was coated on a substrate and subjected to antinic irradiation, to afforded homogeneous transparent film. A mask image was recovered on the film by a light of 365 nm and read by a visible light (λ > 700 nm) without destruction of the image. To erase the recorded image, a white light or a visible light was irradiated. Photochromic quantum yield and photo-induced refractive index change of the diarylethene bound polymer film were determined as 0.12 and 0.0006 respectively. INTRODUCTION Photochromic dyes, dispersed in or bound to polymer matrices, are of significant interest for their potential application in optical memory, switches, and other optoelectronic devices [1]. Among those, diarylethene derivatives have attracted interest for their high photochromic efficiency and thermal stability [2,3]. The photochromic properties of diarylethene molecules arise from photoinduced ring closure/opening process. Photo-induced refractive index change could be attained from a photochromic polymer, in which photochromophores are dispersed in polymer matrices or attached to polymer chains by covalent bonding [4]. Since solid state polymer films containing photochromophores are the demanding media for optical data storage, the studies on the photochromic reactions of various types of photochromic dyes in the polymer matrices are of great importance from the view points of practical applications. In this work, we present photopolymerization of a fluoroalkylacrylate containing diarylethene derivatives and the photochromic behavior of the diarylethene polymer films. C8.24.1
EXPERIMENTAL DETAILS Materials BTF6 was synthesized from benzothiophene in three steps [4,5]. 1-(6'-Acetyl-2'methylbenzo[b]thiophene-3'-yl)-2-(2"-methylbenzo[b]thiophene-3"-yl)hexafluorocyclopentene (AMBTF6) and 1,2-bis(6',6"-bis(acetyl)-2'-methylbenzo[b]thiophene-3'-yl)hexafluorocyclopentene (DAMBTF6) were synthesized from BTF6 in one step [6]. MMBTF6 was synthesized from BTF6 in three steps [4]. TFBDA was synthesized from 2,2,3,3-tetrafluoro1,4-butanediol and acryloylchloride in the presence of triethylamine. Other chemicals and solvents were purchased from
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