Mechanofluorochromism and mechanical force-triggered solid-state [2+2] photocycloaddition in α-cyanostilbene derivatives
Mechanofluorochromism and mechanical force-triggered solid-state [2+2] photocycloaddition in α-cyanostilbene derivatives
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α-氰芪衍生物中的机械荧光显色和机械力触发固态 [2 2] 光环加成
DOI：
10.1016/j.dyepig.2022.110205
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发表时间：
2022-05
影响因子：
4.5
通讯作者：
Xiaofang Chen
中科院分区：
文献类型：
--
作者：
Jundan Huang;Wenjing Wei;Bian Li;Tao Liu;Xiaofang Chen
α-氰基二苯乙烯类化合物是一类荧光光致变色分子，可通过光致异构化或环加成反应实现发光变色或开关开关。与异构化反应相比，光环加成反应由于其关键的分子位置和对分子堆积的排列要求，对其研究较少。本工作合成了联苯基二茂铁化合物1-3，它们具有典型的机械荧光(MFC)响应行为。在力的刺激下，发光颜色发生了从蓝色到绿色的红移，同时也发生了从晶态到非晶态的相变。光致变色荧光反应归因于光诱导的[2+2]环加成反应可以在非晶态而不是在晶体中立即发生。MFC响应可以成功地用于监测光反应过程，从而产生定量的二聚化产物。化合物2的单晶结构揭示了它的光稳定性。基非晶态的准分子的形成与机械剪切共同促进了环加成反应的发生。随后，可以在热或紫外线照射下实现恢复过程。
α-Cyanostilbene derivatives are known as fluorescent photochromic molecules that could be used to realize emission colour change or on/off switching via photo-induced isomerization or cycloaddition. Comparing with isomerization, photocycloaddition is less studied due to its critical molecular position and alignment requirement for molecular packing. In this work, biphenyl-based cyanostilbenic compounds1–3were synthesized, which exhibit characteristic mechanofluorochromic (MFC) response behaviour. Under force stimuli, the luminescent colour has bathochromic shift from blue to green, together with the phase transition from crystal to amorphous state. Photochromic fluorescent response attributed to photo-induced [2 + 2] cycloaddition could take place instantly in amorphous state, rather than crystals. The MFC response can be successfully used to monitor the photoreaction process, giving rise to quantitative dimerized product. The single crystal structure of compound2revealed its photostable feature. The formation of excimers in ground amorphous state, together with the mechanical shearing, facilitates the occurrence of cycloaddition. Subsequently, the recovery process could be achieved thermally or under UV irradiation.
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