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首页> 外文期刊>Acta Crystallographica, Section B. Structural science, crystal engineering and materials >Crystalline state photochromism of 3-furylfulgides: impact of size and bond flexibility of the nonaromatic alkylidene group
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Crystalline state photochromism of 3-furylfulgides: impact of size and bond flexibility of the nonaromatic alkylidene group

机译：3-呋喃呋喃酮的结晶态光致变色：非芳族亚烷基的大小和键柔性的影响

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摘要

3-Furylfulgides are photochromic compounds showing high thermal stability in their closed forms. However, their photochromic properties in the solid state should be improved further to fabricate molecular devices. Understanding how the size and the flexibility of the non-aromatic alkylidene moiety alter the crystalline state photochromic properties is also important here, as the alkylidene group is directly involved in the photochromic ring closing and opening reactions. The synthesis of four 3-furylfulgides composed of different alkylidene groups (rigid isopropyl, flexible 2-butyl, rigid cyclopentyl and flexible cyclohexyl), their crystal structures and structure–photochromic property correlation in the crystalline state are reported here. Crystallographic data along with reaction cavity volumes calculated using the program CAVITY [Ohashi et al. (1981), J. Am. Chem. Soc. 103, 5805–5812] disclosed that fulgides with flexible groups at the ring closing site have more free volume around the reactive area in the crystal lattice, which can provide more space for the atomic movements in the reaction and flexibility can reduce the strain built up in the closed C-isomers by making conformations. According to UV–vis spectroscopic data, a higher yield of C-isomers and a better fatigue resistance were obtained for the 3-furylfulgide with the largest and flexible cyclohexyl group showing greater photochromic properties in the crystalline state than the fulgide containing the smallest and rigid isopropyl group.
机译：3-呋喃酮酸酯是一种光致变色化合物，在其封闭形式下具有很高的热稳定性。然而，它们的固态光致变色性质应进一步改善以制造分子器件。在这里，了解非芳族亚烷基部分的大小和柔韧性如何改变结晶态光致变色特性也很重要，因为亚烷基直接参与光致变色环的闭合和打开反应。本文报道了由不同亚烷基（刚性异丙基，柔性2-丁基，刚性环戊基和柔性环己基）组成的四种3-呋喃基呋喃酮的合成，它们的晶体结构以及晶体状态下的结构-光致变色性质相关性。晶体学数据以及使用腔CAVITY [Ohashi et al。 （1981），J。Am。化学Soc。 103，5805–5812]公开了在闭环位点处具有柔性基团的全氟化合物在晶格中的反应区域周围具有更多的自由体积，这可以为反应中的原子运动提供更多的空间，并且柔性可以减少所建立的应变通过形成构象在封闭的C-异构体中。根据紫外可见光谱数据，具有最大且柔性的环己基的3-呋喃基呋喃酮的C异构体收率更高，并且具有更好的抗疲劳性，与含有最小且刚性的fulgide相比，在结晶状态下显示出更大的光致变色特性。异丙基。

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