Enhancement of Negative Photochromic Properties of Naphthalene-Bridged Phenoxyl-Imidazolyl Radical Complex.,ChemPhysChem

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Enhancement of Negative Photochromic Properties of Naphthalene-Bridged Phenoxyl-Imidazolyl Radical Complex.
ChemPhysChem ( IF 2.3 ) Pub Date : 2020-06-25 , DOI: 10.1002/cphc.202000296
Hiroki Ito ₁ , Katsuya Mutoh ₁ , Jiro Abe ₁

Affiliation

Negative photochromism has increased attention as a light‐switch for functional materials. A development of fast photochromic molecules has been also expected because a rapid thermal back reaction within a millisecond time scale is useful for real‐time switching. Herein, we synthesized the derivatives of the naphthalene‐bridged phenoxyl‐imidazolyl radical complex (Np−PIC) showing the negative photochromism to demonstrate the efficient strategy to increase the visible light sensitivity and to control the thermal back reaction rates. The distances of the C−C bond of the transient 2,4’‐isomer shows good agreement with the thermodynamic stability, leading to the control of the thermal back reaction rate. We revealed the cyclic voltammetry and the DFT calculations are efficient to predict the characters of the HOMO and LUMO. The introduction of the electron‐withdrawing dicyanoquinodimethane group is efficient to induce the photochromic reaction with increased visible‐light sensitivity by the expansion of the π‐conjugation. The results will give an important insight for the future development of fast‐responsive negative photochromic molecules.

中文翻译：

萘桥联苯氧基-咪唑基自由基复合物的负光致变色性能增强。

负光致变色作为功能材料的光开关已引起越来越多的关注。快速光致变色分子的发展也被期待，因为在毫秒级的时间内快速的热逆反应对于实时切换很有用。在这里，我们合成了显示负光致变色现象的萘桥苯氧基-咪唑基自由基复合物（Np-PIC）的衍生物，以证明提高可见光敏感性和控制热反反应速率的有效策略。瞬态2,4'-异构体的CC键距离与热力学稳定性显示出良好的一致性，从而控制了热逆反应速率。我们揭示了循环伏安法和DFT计算可有效预测HOMO和LUMO的特征。引入吸电子的二氰基喹二甲烷基团可通过π共轭的扩展有效地诱导光致变色反应，从而增加可见光灵敏度。这些结果将为快速响应的负性光致变色分子的未来发展提供重要的见识。

更新日期：2020-06-25

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