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Substitution effect on the photochromic properties of benzo[b]thiophene-1,1-dioxide based diarylethenes

机译:对苯并[B]噻吩-1,1-二氧化二氧化芳基二氧化芳基的光致变色特性的替代作用

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摘要

Benzo[b]thiophene-1,1-dioxide based diarylethenes (DAEs), BTT-1 to BTT-4, containing methyl, phenyl, formyl and triphenylamine groups at the 5,5'-position of the thiophene rings have been developed for gaining an insight into the substituent effect on the absorption and photochromic properties. Electron-donating substituents, such as phenyl and triphenylamine groups, are found to be effective at shifting the absorption band to a longer wavelength and decreasing the cyclization quantum yield. The electron-withdrawing formyl group can increase the cyclization quantum yield, but it reduces the thermal stability of the ring-closed isomer to some extent. BTT-4 bearing a triphenylamine group shows the poorest fatigue resistance among these four compounds, which is possibly due to the larger extended pi-conjugation length in the ring-closed isomer. BTT-2 bearing a phenyl unit undergoes typical photochromic reaction not only in solution, but also in PMMA thin film and in bulky crystals with excellent fatigue resistance and thermal stability.
机译:已经开发出含有甲基,苯基,甲酰基和三苯基和三苯胺基团的苯并[B]噻吩-1,1-二氧化氧化物基二氧化芳基(Daes),Btt-1至Btt-4在噻吩环的5,5'-位置处的甲基,苯基,甲酰基和三苯胺基团对吸收和光致变色特性的取代基效应进行了解。发现电子提供的取代基,例如苯基和三苯胺基团,在将吸收带移至较长波长并降低环化量子产率时有效。吸电子甲酰基可以增加环化量子产率,但它在一定程度上降低了环形异构体的热稳定性。 BTT-4承载三苯胺基团显示这四种化合物中最贫困的疲劳性,这可能是由于环闭异构体中较大的延伸的PI缀合长度。 BTT-2轴承苯基单元不仅在溶液中经历典型的光致变色反应,而且在PMMA薄膜和庞大的晶体中具有优异的疲劳性和热稳定性。

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  • 来源
    《RSC Advances》 |2015年第106期|共9页
  • 作者单位

    Shanghai Normal Univ Dept Chem Shanghai 200234 Peoples R China;

    E China Univ Sci &

    Technol Shanghai Key Lab Funct Mat Chem Collaborat Innovat Ctr Coal Based Energy I CCE Key Lab Adv Mat Shanghai 200237 Peoples R China;

    KTH Royal Inst Technol Sch Biotechnol Div Theoret Chem &

    Biol SE-10691 Stockholm Sweden;

    E China Univ Sci &

    Technol Shanghai Key Lab Funct Mat Chem Collaborat Innovat Ctr Coal Based Energy I CCE Key Lab Adv Mat Shanghai 200237 Peoples R China;

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  • 原文格式 PDF
  • 正文语种 eng
  • 中图分类 化学;
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