The carboxyl derivatives of 6,8-di-(tert.-butyl)phenoxazine: Synthesis, oxidation reactions and fluorescence

Ivakhnenko, E. P.; Knyazev, Pavel A.; Романенко, Г. В.; Kovalenko, A. A.; Ivakhnenko, T. E.; Revinskii, Yurii V.

doi:10.1016/j.tet.2018.12.047

Cited by 8 publications

(4 citation statements)

References 24 publications

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“…4). V to a radical-anion and then undergoes irreversible reduction at Е1/2 RED2 = -1.91 V and irreversible oxidation at Е1/2 OX = 0.48 V. These CV parameters are close to those recorded for triphenodioxazines [20]. The energies of the HOMO and LUMO orbitals assessed on the basis of the CV and electronic absorption spectra data are given in Table 3.…”

Section: Resultssupporting

confidence: 70%

Facile Approach to the N,O,S-Heteropentacycles via Condensation of Sterically Crowded 3H-Phenoxazin-3-one with ortho-amino-, hydroxy- and mercaptoanilines

Ivakhnenko,

Malay,

Knyazev

et al. 2023

Preprint

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A convenient method for the synthesis of a series of 2-arylamino-3H-phenoxazin-3-ones based on the nucleophilic substitution reaction between sterically crowded 3H-phenoxazin-3-one and arylamines performed by short-term heating of the melted reactants at 230-250 °C is described and the compounds are characterized by means of single-crystal X-ray crystallography, NMR, UV/vis, IR spectroscopy and cyclic voltammetry. Involvement into the reaction of arylamines with o-amino-, o-hydroxy and o-mercapto-substituents widens its scope and provides for an access to derivatives of N,O- and N,S-heteropentacyclic quinoxalinophenoxazine, triphenodioxazine and oxazinophenothiazine systems.

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Section: Resultssupporting

confidence: 70%

Facile Approach to the N,O,S-Heteropentacycles via Condensation of Sterically Crowded 3H-Phenoxazin-3-one with ortho-amino-, hydroxy- and mercaptoanilines

Ivakhnenko,

Malay,

Knyazev

et al. 2023

Preprint

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“…2 , diradicaloid 1a can be simply and efficiently synthesized in two steps involving a facile condensation reaction between benzidine 2a and two equivalent amounts of 3,5-di- tert -butyl catechol 3 , and a cascade reaction in the presence of lead (IV) oxide, without any purification by column chromatography. The cascade reaction sequence might consist of an oxidation reaction, an intramolecular cyclization 42 and a subsequent oxidative aromatization step, accompanied by the generation of unstable quinone imines 5 and a highly reactive dihydro intermediate 6 . The scope of the substituted benzidine substrates was surveyed and the preliminary results indicated that the substrate scope of this cascade reaction was restricted to benzidine 2a and 3,3’-dimethylbenzidine 2b , e.g., all attempts to synthesize diradicaloids 1c and 1d were unsuccessful (for details see the Supplementary Information (SI), Synthesis and characterization section).…”

Section: Resultsmentioning

confidence: 99%

Design of an open-shell nitrogen-centered diradicaloid with tunable stimuli-responsive electronic properties

et al. 2022

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Organic diradicaloids usually display an open-shell singlet ground state with significant singlet diradical character (y0) which endow them with intriguing physiochemical properties and wide applications. In this study, we present the design of an open-shell nitrogen-centered diradicaloid which can reversibly respond to multiple stimuli and display the tunable diradical character and chemo-physical properties. 1a was successfully synthesized through a simple and high-yielding two-step synthetic strategy. Both experimental and calculated results indicated that 1a displayed an open-shell singlet ground state with small singlet-triplet energy gap (ΔES−T = −2.311 kcal mol−1) and a modest diradical character (y0 = 0.60). Interestingly, 1a was demonstrated to undergo reversible Lewis acid-base reaction to form acid-base adducts, which was proven to effectively tune the ground-state electronic structures of 1a as well as its diradical character and spin density distributions. Based on this, we succeeded in devising a photoresponsive system based on 1a and a commercially available photoacid merocyanine (MEH). We believe that our studies including the molecular design methodology and the stimuli-responsive organic diradicaloid system will open up a new way to develop organic diradicaloids with tunable properties and even intelligent-responsive diradicaloid-based materials.

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“…The intermolecular cyclization with the formation of phenoxazinone derivatives may be one of the minor reactions in the electrooxidation of APH 1 or APH 5. 68 Hence, compounds APH 1, 3, 5, 6-8 cannot be applied as redox mediators of thiol oxidation.…”

Section: Resultsmentioning

confidence: 99%

Substituted o-Aminophenols as Redox-Mediators in the Thiol Oxidation to Unsymmetrical Disulfides

Burmistrova

Galustyan

Smolyaninov

et al. 2021

J. Electrochem. Soc.

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A number of substituted o-aminophenols has been investigated as redox mediators of the thiol oxidation to disulfides. The electrooxidation of o-aminophenols leads to the corresponding o-iminobenzoquinones. These compounds react with thiols in the solution with a formation of disulfides. It was established that the use of 4,6-di-tert-butyl-2-(tert-butylamino)phenol as a redox mediator can reduce the overpotential of the thiol oxidation by 0.2–1.4 V depending on the nature of the coupling thiols. The unsymmetrical disulfides with alkyl, aryl, and heteroaryl substituents were obtained as the result of the indirect electrosynthesis.

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The carboxyl derivatives of 6,8-di-(tert.-butyl)phenoxazine: Synthesis, oxidation reactions and fluorescence

Cited by 8 publications

References 24 publications

Facile Approach to the N,O,S-Heteropentacycles via Condensation of Sterically Crowded 3H-Phenoxazin-3-one with ortho-amino-, hydroxy- and mercaptoanilines

Facile Approach to the N,O,S-Heteropentacycles via Condensation of Sterically Crowded 3H-Phenoxazin-3-one with ortho-amino-, hydroxy- and mercaptoanilines

Design of an open-shell nitrogen-centered diradicaloid with tunable stimuli-responsive electronic properties

Substituted o-Aminophenols as Redox-Mediators in the Thiol Oxidation to Unsymmetrical Disulfides

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