In search of open-framework channels: reactions of amines with 4,5-difluoro-1,2-dinitrobenzene and 1,3-difluoro-4,6-dinitrobenzene

Michael J Plater; William T A Harrison

doi:10.1177/17475198251346820

In search of open-framework channels: reactions of amines with 4,5-difluoro-1,2-dinitrobenzene and 1,3-difluoro-4,6-dinitrobenzene

Michael J Plater^* (Corresponding Author)
, William T A Harrison

^*Corresponding author for this work

Chemistry

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

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Abstract

Three potential hosts with an amine-conjugated nitro group, derived from reacting 4,5-difluoro-1,2-dinitrobenzene or 1,3-difluoro-4,6-dinitrobenzene with different amines, have been crystallised and their structures solved by X-ray single crystal structure determinations. The first of these gives a complex structure in space group P31 with Z’ = 12 owing to different conformations of the butyl side chains. ‘Doughnut’ like hydrogen-bonded six rings occur in the extended structure with F. . .F separations across the rings of about 13 Å, but there is no overall porosity because the doughnuts are staggered with respect to the c-direction of the trigonal unit cell. The other two potential hosts did not form porous networks.

Original language	English
Number of pages	8
Journal	Journal of Chemical Research
Volume	49
Issue number	3
Early online date	16 Jun 2025
DOIs	https://doi.org/10.1177/17475198251346820
Publication status	Published - Jun 2025

Bibliographical note

Open Access via the Sage agreement

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

Data Availability Statement

This paper and the supplementary will be made available in the Aberdeen University Duncan Rice library, https://www.abdn.ac.uk/library/

Funding

The author(s) received no financial support for the research, authorship, and/or publication of this article.

Keywords

exploratory
framework
nucleophiles
porous
sequential
Voids

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Cite this

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title = "In search of open-framework channels: reactions of amines with 4,5-difluoro-1,2-dinitrobenzene and 1,3-difluoro-4,6-dinitrobenzene",

abstract = "Three potential hosts with an amine-conjugated nitro group, derived from reacting 4,5-difluoro-1,2-dinitrobenzene or 1,3-difluoro-4,6-dinitrobenzene with different amines, have been crystallised and their structures solved by X-ray single crystal structure determinations. The first of these gives a complex structure in space group P31 with Z{\textquoteright} = 12 owing to different conformations of the butyl side chains. {\textquoteleft}Doughnut{\textquoteright} like hydrogen-bonded six rings occur in the extended structure with F. . .F separations across the rings of about 13 {\AA}, but there is no overall porosity because the doughnuts are staggered with respect to the c-direction of the trigonal unit cell. The other two potential hosts did not form porous networks.",

keywords = "exploratory, framework, nucleophiles, porous, sequential, Voids",

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

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AU - Plater, Michael J

AU - Harrison, William T A

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

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N2 - Three potential hosts with an amine-conjugated nitro group, derived from reacting 4,5-difluoro-1,2-dinitrobenzene or 1,3-difluoro-4,6-dinitrobenzene with different amines, have been crystallised and their structures solved by X-ray single crystal structure determinations. The first of these gives a complex structure in space group P31 with Z’ = 12 owing to different conformations of the butyl side chains. ‘Doughnut’ like hydrogen-bonded six rings occur in the extended structure with F. . .F separations across the rings of about 13 Å, but there is no overall porosity because the doughnuts are staggered with respect to the c-direction of the trigonal unit cell. The other two potential hosts did not form porous networks.

AB - Three potential hosts with an amine-conjugated nitro group, derived from reacting 4,5-difluoro-1,2-dinitrobenzene or 1,3-difluoro-4,6-dinitrobenzene with different amines, have been crystallised and their structures solved by X-ray single crystal structure determinations. The first of these gives a complex structure in space group P31 with Z’ = 12 owing to different conformations of the butyl side chains. ‘Doughnut’ like hydrogen-bonded six rings occur in the extended structure with F. . .F separations across the rings of about 13 Å, but there is no overall porosity because the doughnuts are staggered with respect to the c-direction of the trigonal unit cell. The other two potential hosts did not form porous networks.

KW - exploratory

KW - framework

KW - nucleophiles

KW - porous

KW - sequential

KW - Voids

U2 - 10.1177/17475198251346820

DO - 10.1177/17475198251346820

M3 - Article

SN - 0308-2342

VL - 49

JO - Journal of Chemical Research

JF - Journal of Chemical Research

IS - 3

ER -

In search of open-framework channels: reactions of amines with 4,5-difluoro-1,2-dinitrobenzene and 1,3-difluoro-4,6-dinitrobenzene

Abstract

Bibliographical note

Data Availability Statement

Funding

Keywords

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