New Functionalized Phenoxazines and Phenothiazines

M. John Plater; William T. A. Harrison

doi:10.1021/acsomega.3c06461

New Functionalized Phenoxazines and Phenothiazines

M. John Plater, William T. A. Harrison

Chemistry

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

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Abstract

The reaction of either 2-aminophenol or 2-(N-methylamino)phenol with 1,2-difluoro-4,5-dinitrobenzene and sodium carbonate in EtOH gives 2,3-dinitrophenoxazines. One nitro group, conjugated to the aryl ether, was displaced from 2,3-dinitro-10-methylphenoxazine with different nucleophiles: BuNH2, KOEt, and KOH. The reaction of 2-aminothiophenol with 1,2-difluoro-4,5-dinitrobenzene under the same conditions gives 2,3-dinitrophenothiazine. This reacted with BuNH2 forming 2-butylamino-3-nitrophenothiazine. The dihedral angles of the different compounds are compared.

Original language	English
Pages (from-to)	44163–44171
Number of pages	9
Journal	ACS Omega
Volume	8
Issue number	46
Early online date	9 Nov 2023
DOIs	https://doi.org/10.1021/acsomega.3c06461
Publication status	Published - 21 Nov 2023

Bibliographical note

The authors thank the U.K. EPSRC National Mass Spectrometry Service Centre for mass spectrometric data and the U.K. National Crystallography Centre (University of Southampton) for the X-ray data collections. M.J.P. performed all synthesis and obtained the characterization data, and W.T.A.H. solved the crystallographic data sets. Data sets were obtained free of charge from the National Crystallography Center, Southampton University.

Data Availability Statement

Supporting Information
The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acsomega.3c0646

1 The proton and carbon NMR data for all compounds in the Experimental Section (Figures S1−S19) (PDF)

Accession Codes
CCDC 2291273 (compound13), CCDC 2291274 (com-pound 14), CCDC 2291275 (compound 15), CCDC 2291276 (compound 16), CCDC 2291277 (compound 17), CCDC 2291278 (compound 19), and CCDC 2291279 (compound 20) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/datarequest/cif.

Keywords

pentacene
phenoxazine
phenothiazine
dinitrobenzene
organic electronics

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Cite this

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title = "New Functionalized Phenoxazines and Phenothiazines",

abstract = "The reaction of either 2-aminophenol or 2-(N-methylamino)phenol with 1,2-difluoro-4,5-dinitrobenzene and sodium carbonate in EtOH gives 2,3-dinitrophenoxazines. One nitro group, conjugated to the aryl ether, was displaced from 2,3-dinitro-10-methylphenoxazine with different nucleophiles: BuNH2, KOEt, and KOH. The reaction of 2-aminothiophenol with 1,2-difluoro-4,5-dinitrobenzene under the same conditions gives 2,3-dinitrophenothiazine. This reacted with BuNH2 forming 2-butylamino-3-nitrophenothiazine. The dihedral angles of the different compounds are compared.",

keywords = "pentacene, phenoxazine, phenothiazine, dinitrobenzene, organic electronics",

author = "Plater, {M. John} and Harrison, {William T. A.}",

note = "The authors thank the U.K. EPSRC National Mass Spectrometry Service Centre for mass spectrometric data and the U.K. National Crystallography Centre (University of Southampton) for the X-ray data collections. M.J.P. performed all synthesis and obtained the characterization data, and W.T.A.H. solved the crystallographic data sets. Data sets were obtained free of charge from the National Crystallography Center, Southampton University.",

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T1 - New Functionalized Phenoxazines and Phenothiazines

AU - Plater, M. John

AU - Harrison, William T. A.

N1 - The authors thank the U.K. EPSRC National Mass Spectrometry Service Centre for mass spectrometric data and the U.K. National Crystallography Centre (University of Southampton) for the X-ray data collections. M.J.P. performed all synthesis and obtained the characterization data, and W.T.A.H. solved the crystallographic data sets. Data sets were obtained free of charge from the National Crystallography Center, Southampton University.

PY - 2023/11/21

Y1 - 2023/11/21

N2 - The reaction of either 2-aminophenol or 2-(N-methylamino)phenol with 1,2-difluoro-4,5-dinitrobenzene and sodium carbonate in EtOH gives 2,3-dinitrophenoxazines. One nitro group, conjugated to the aryl ether, was displaced from 2,3-dinitro-10-methylphenoxazine with different nucleophiles: BuNH2, KOEt, and KOH. The reaction of 2-aminothiophenol with 1,2-difluoro-4,5-dinitrobenzene under the same conditions gives 2,3-dinitrophenothiazine. This reacted with BuNH2 forming 2-butylamino-3-nitrophenothiazine. The dihedral angles of the different compounds are compared.

AB - The reaction of either 2-aminophenol or 2-(N-methylamino)phenol with 1,2-difluoro-4,5-dinitrobenzene and sodium carbonate in EtOH gives 2,3-dinitrophenoxazines. One nitro group, conjugated to the aryl ether, was displaced from 2,3-dinitro-10-methylphenoxazine with different nucleophiles: BuNH2, KOEt, and KOH. The reaction of 2-aminothiophenol with 1,2-difluoro-4,5-dinitrobenzene under the same conditions gives 2,3-dinitrophenothiazine. This reacted with BuNH2 forming 2-butylamino-3-nitrophenothiazine. The dihedral angles of the different compounds are compared.

KW - pentacene

KW - phenoxazine

KW - phenothiazine

KW - dinitrobenzene

KW - organic electronics

U2 - 10.1021/acsomega.3c06461

DO - 10.1021/acsomega.3c06461

M3 - Article

C2 - 38027375

SN - 2470-1343

VL - 8

SP - 44163

EP - 44171

JO - ACS Omega

JF - ACS Omega

IS - 46

ER -

New Functionalized Phenoxazines and Phenothiazines

Abstract

Bibliographical note

Data Availability Statement

Keywords

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