Redox-Driven Logic Gates Based on Intramolecular Weak Interactions in Pyridyl-Containing Diarylnitroxides

Oleg A. Levitskiy; Igor V. Prolubshikov; Alexey V. Bogdanov; Tatiana V. Magdesieva

doi:10.1002/ejoc.202400323

Redox-Driven Logic Gates Based on Intramolecular Weak Interactions in Pyridyl-Containing Diarylnitroxides

Oleg A. Levitskiy, Igor V. Prolubshikov, Alexey V. Bogdanov, Tatiana V. Magdesieva^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

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Abstract

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.

Original language	English
Article number	e202400323
Journal	European Journal of Organic Chemistry
Volume	27
Issue number	27
DOIs	https://doi.org/10.1002/ejoc.202400323
Publication status	Published - 15 Jul 2024
Externally published	Yes

All Science Journal Classification (ASJC) codes

Physical and Theoretical Chemistry
Organic Chemistry

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title = "Redox-Driven Logic Gates Based on Intramolecular Weak Interactions in Pyridyl-Containing Diarylnitroxides",

abstract = "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.",

author = "Levitskiy, {Oleg A.} and Prolubshikov, {Igor V.} and Bogdanov, {Alexey V.} and Magdesieva, {Tatiana V.}",

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doi = "10.1002/ejoc.202400323",

language = "English",

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T1 - Redox-Driven Logic Gates Based on Intramolecular Weak Interactions in Pyridyl-Containing Diarylnitroxides

AU - Levitskiy, Oleg A.

AU - Prolubshikov, Igor V.

AU - Bogdanov, Alexey V.

AU - Magdesieva, Tatiana V.

PY - 2024/7/15

Y1 - 2024/7/15

N2 - 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.

AB - 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.

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DO - 10.1002/ejoc.202400323

M3 - Article

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JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

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ER -

Redox-Driven Logic Gates Based on Intramolecular Weak Interactions in Pyridyl-Containing Diarylnitroxides

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