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Redox‐Driven Logic Gates Based on Intramolecular Weak Interactions in Pyridyl‐Containing Diarylnitroxides
European Journal of Organic Chemistry ( IF 2.5 ) Pub Date : 2024-06-28 , DOI: 10.1002/ejoc.202400323
Oleg A. Levitskiy 1 , Igor V. Prolubshikov 1 , Alexey V. Bogdanov 1 , Tatiana V. Magdesieva 1
Affiliation  

A new stable diarylnitroxide with two 2‐pyridyl groups in the ortho‐positions of the phenyl rings, in the close vicinity to the NO fragment, was obtained. Conformational flexibility of the molecule provides stimuli‐responsive reversible on/off switching of the intramolecular interactions, stabilizing the oxidized and reduced states of the nitroxide (due to the n‐π* interaction and the intramolecular H‐bonding, respectively) and giving rise to novel properties. The intrinsic electrofluorochromism of the oxoammonium cation rigidified by the intramolecular N−O bond between the pyridyl lone pair and the O atom was first disclosed. Structural simplicity and facile synthesis of the diarylnitroxide make it promising for creating novel types of redox‐switchable molecular logic gates.

中文翻译:


基于含吡啶基二芳基氮氧化合物分子内弱相互作用的氧化还原驱动逻辑门



获得了一种新的稳定的二芳基氮氧化物,其苯环的邻位上有两个 2-吡啶基,紧邻 NO 片段。分子的构象灵活性提供了分子内相互作用的刺激响应性可逆开/关切换,稳定了硝基氧的氧化态和还原态(分别由于 n-π* 相互作用和分子内氢键),并产生新颖的特性。首次公开了通过吡啶基孤对和 O 原子之间的分子内 N-O 键刚性化的氧铵阳离子的本征电荧光变色现象。二芳基氮氧化物的结构简单且易于合成,使其有望用于创建新型氧化还原可切换分子逻辑门。
更新日期:2024-06-28
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