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Keywords = hexasubstituted benzene

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8 pages, 4572 KiB  
Communication
Crystal Structure and Hirshfeld Surface Analysis of Hexakis(acetoxymethyl)benzene
by Manuel Stapf, Wilhelm Seichter and Monika Mazik
Molbank 2025, 2025(2), M2008; https://doi.org/10.3390/M2008 - 16 May 2025
Viewed by 983
Abstract
Representatives of the hexasubstituted benzene derivatives, also known as hexa-hosts, have been the subject of extensive studies in solution and in the solid state, including the investigation of their ability to act as artificial receptors for various substrates, as well as detailed conformational [...] Read more.
Representatives of the hexasubstituted benzene derivatives, also known as hexa-hosts, have been the subject of extensive studies in solution and in the solid state, including the investigation of their ability to act as artificial receptors for various substrates, as well as detailed conformational analyses. In this paper, we describe the X-ray crystal structure of hexakis(acetoxymethyl)benzene (1), a member of the above class of compounds. The molecules of 1 adopt an aaabbb conformation, in which three side-arms point to the same face of the central benzene ring, while the other three point in the opposite direction. As the compound lacks strong hydrogen bond donors, C–H···O hydrogen bonds connect the molecules to a three-dimensional supramolecular network. According to the Hirshfeld surface analysis, the H∙∙∙O/O∙∙∙H interactions represent the major contribution of the molecular Hirshfeld surface. Full article
(This article belongs to the Section Structure Determination)
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10 pages, 1507 KiB  
Article
Supramolecular Weaving by Halogen-Bonding in Functionality-Rich Hexasubstituted Aromatic Synthons
by Matteo Catenazzi, Andrea Nitti, Massimo Boiocchi, Gabriele Bianchi, Riccardo Po and Dario Pasini
Materials 2023, 16(4), 1678; https://doi.org/10.3390/ma16041678 - 17 Feb 2023
Viewed by 2046
Abstract
Hexasubstituted benzenes are interesting platforms for the generation of functional materials, whose applications span from supramolecular recognition to organic electronics. Their synthesis is difficult to achieve by controlling multiple substitution steps of all hydrogen atoms on the aromatic benzene skeleton, so, often, cycloaddition [...] Read more.
Hexasubstituted benzenes are interesting platforms for the generation of functional materials, whose applications span from supramolecular recognition to organic electronics. Their synthesis is difficult to achieve by controlling multiple substitution steps of all hydrogen atoms on the aromatic benzene skeleton, so, often, cycloaddition reactions from disubsituted alkynes are used. In this work, we report a novel, straightforward route to C3-symmetrical hexasubstituted aromatic synthons with a diverse and rich pattern of functionalities, and we report about their packing mode in the crystals, in which, unprecedentedly, directional, strong halogen bonding interactions are capable of forming bidimensional supramolecular weaving. Full article
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14 pages, 6245 KiB  
Article
The Influence of the Intramolecular 2D Interactions on the Physicochemical Properties of Hexasubstituted Benzene Derivatives
by Agata Szlapa-Kula, Sławomir Kula, Patrycja Filipek, Stanisław Krompiec and Michał Filapek
Energies 2023, 16(1), 480; https://doi.org/10.3390/en16010480 - 1 Jan 2023
Viewed by 1863
Abstract
This paper contains a comprehensive study regarding the synthesis and physicochemical properties of new hexasubstitued benzene derivatives. In this work, three compounds of this type (including two electropolymerisable monomers) were synthesized in a one-step reaction with good yields ranging from 34% to 56%. [...] Read more.
This paper contains a comprehensive study regarding the synthesis and physicochemical properties of new hexasubstitued benzene derivatives. In this work, three compounds of this type (including two electropolymerisable monomers) were synthesized in a one-step reaction with good yields ranging from 34% to 56%. A thermal investigation shows that this type of compound is stable up to 360 °C (10% weight loss temperature). The influence of the substituents in the first and second position of the central benzene on the stability, luminescence, and (spectro)electrochemical behavior was thoroughly studied with the aid of theoretical calculations. In each case, strong blue shifting of the π-π* transition (according to 1,4-disubstitued analogs) was observed, proving this moieties’ orthogonal orientation. In the case of derivatives with a Bt-core-Bt formula (where Bt = 2,2′-bithiophene-5-yl), an electrochemical oxidation process transformed them into conducting polymers. The polymer presents extraordinary stability during multiple p-doping; thus, spectroelectrochemical measurements of polymeric films were also performed. Full article
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5 pages, 818 KiB  
Short Note
Ethyl 4,4''-Dibromo-5'-(butylamino)-2',6'-dinitro-[1,1':3',1''-terphenyl]-4'-carboxylate
by Damiano Rocchi, Juan F. González and J. Carlos Menéndez
Molbank 2015, 2015(1), M848; https://doi.org/10.3390/M848 - 18 Mar 2015
Viewed by 3250
Abstract
Ethyl 4,4''-Dibromo-5'-(butylamino)-2',6'-dinitro-[1,1':3',1''-terphenyl]-4'-carboxylate (2) which is a m-terphenyl derivative containing an hexasubstituted, highly functionalized substituted benzene core, has been synthesized. Full article
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