cas 24848-78-0, 4,8-dibromo-1H,3H-Benzo[1,2-c:4,5-c']difuran-1,3,5,7-tetrone

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Synthesis of bromo- and iodo-substituted pyromellitic diimide-based [2+2]- and [3+3]macrocycles, and their absorption spectra and electrochemical and inclusion properties
New pyromellitic diimide-based tetrabromo[2+2]macrocycle ([2+2]MC) 2, tribromo- and hexabromo[3+3]MCs 3a and 3b, as well as triiodo[3+3]MC 3c were synthesized as structural units of covalently bound nanotubes, and their absorption spectra and redox properties, as well as inclusion phenomena of the [2+2]MC 2 were reported. Tetrabromo[2+2]MC 2 forms a 1:1 inclusion complex with toluene, whose structure was revealed by X-ray structural analysis.
Ershad Halim, Md.,Bandyopadhyay, Arkasish,Sun, Liansheng,Tao, Keisuke,Sangvikar, Yogesh Shashikant,Miyazaki, Takaaki,Watanabe, Motonori,Ideta, Keiko,Matsumoto, Taisuke,Goto, Kenta,Shinmyozu, Teruo
p. 6970 - 6974
(2015)
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A study on the synthesis, characterization, structural optimization, and conformational behaviors of bromo-substituted pyromelliticdiimide-based [2+2] macrocycle as structural units of covalently linked molecular tubes
Synthesis and structural, photo physical, and conformational behaviors at variable temperature and structural optimization of the pyromelliticdiimide-based bromo-substituted [2 + 2] macrocycles are described. Cyclization of the diamine (3) with dianhydride (4) in THF, followed by dehydration of the resultant amic acids resulted in the isolation of the bromo-substituted [2 + 2] macrocycle 1 (4.5%). The dynamic temperature-dependent 1H NMR spectra and MO calculations revealed the presence of two possible conformers for the [2 + 2] macrocycle 1. The UV/Vis spectrum of 1 reveals the presence of a weak intramolecular CT interaction of electron-withdrawing pyromelliticdiimide moiety with the electron-donating hexyloxy-substituted xylyl moiety. The cyclic voltammetric measurement shows two two-electron reversible reduction processes.
Bandyopadhyay, Arkasish,Halim, Md. Ershad,Hossain, Md. Elius,Shinmyozu, Teruo
(2020/04/17)

Synthesis and photophysical investigations of pyromellitic diimide based small molecules
The present work reports on the highly efficient microwave assisted Suzuki coupling reaction for obtaining pyromellitic diimide based symmetrical small molecules with donor-acceptor-donor (D-A-D) configuration. Electron rich bithiophene is employed as a donor and alkyl substituted pyromellitic diimide units are explored as acceptors to get the desired small molecules. In order to study the relation between chemical structures and material properties, the prepared compounds were characterized in detail using absorption spectroscopy, cyclic voltammetry and thermograviometric analysis. The compounds exhibited good thermal stabilities with high decomposition temperature. Photophysical investigations of the newly synthesized pyromellitic diimide based small molecules, suggests these materials as potential candidates for organic electronic applications.
Bathula, Chinna,Mallikarjuna,Kadam, Abhijit,Shrestha, Nabeen K.,Khadtare, Shubhangi,Mane, Suresh D.,Kim, Haekyoung
p. 20 - 24
(2019/02/12)

HIGH-AND LOW-POTENTIAL, WATER-SOLUBLE, ROBUST QUINONES
Substituted hydroquinones, 1,4-quinones, catechols, 1,2-quinones, anthraquinones, and anthrahydroquinones are disclosed herein. The substituted hydroquinones and catechols have the formula: while the substituted 1,4-quinones or 1,2-have the corresponding oxidized structure (1,4- benzoquinones and 1,2-benzoquinones). One or more of R1, R2, R3 and R4 include a sulfonate moiety, a sulfonimide moiety, or a phosphonate moiety, and any of R1, R2, R3 and R4 that do not include one of these moieties include an alkyl, a cycloalkyl, a thioether, a sulfoxide, a sulfone, a haloalkyl, a halogen, a nitrile, an imide, a pyrazole, or combinations thereof. The substituted anthraquinones have the formula: while the substituted anthrahydroquinones have the corresponding reduced structure. One or more of R1-R8 have a sulfonate or phosphate tethered to the ring by a thi other, amine, or ether including one or more alkyl groups. Any of R1-R8 that do not contain one of these moieties include an alkyl, a cycloalkyl, a thiother, a sulfoxide, a sulfone, a haloalkyl, a halogen, a hydroxyl, an alkoxyl, an ether, an amine, or hydrogen The substituted hydroquinones, 1,4-quinones, catechols, 1,2-quinones, anthraquinones, or anthrahydroquinones are soluble in water, stable in aqueous acid solutions, and have useful reduction potentials in the oxidized form. Accordingly, they can be used as redox mediators in emerging technologies, such as in mediated fuel cells or organic-mediator flow batteries.
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Paragraph 00104

(2018/09/21)

A molecular structure and crystallization correlation study of pyromellitic diimide-based conjugated copolymers
Three pyromellitic diimide(PMDI)-based polymers—poly(pyromellitic diimide-co-bithiophene) [poly(PMDI-BTh)], poly(pyromellitic diimide-co-tetrathiophene) [poly(PMDI-TTh)], and poly(pyromellitic diimide-co-benzodithio- phene) [poly(PMDI-BDTTh)]—are synthesized to study the influence of different thiophene-containing electron-donating groups on the crystallizability of PMDI-based conjugated polymers. Computer simulation using Density Functional Theory (DFT) [Gaussian B3LYP/6–31 + G(d,p)] indicates that poly(PMDI-BDTTh) has a more planar molecular structure than the other two copolymers. Powder XRD diffraction experiment of the poly(PMDI-BDTTh) shows a diffraction peak at about 2θ = 6.0°, but no diffraction peak occurs for poly(PMDI-BTh) and poly(PMDI-TTh). Although PMDI is a planar structure that is favorable for the molecular aggregation, a comonomer with planar structure seems to be very crucial in order to synthesize a crystallizable push–pull-type PMDI-based conjugated copolymer.
Tsai, Ming-Chia,Liu, Ja-Wei,Huang, Ping-Tsung
p. 828 - 834
(2018/03/21)

Organic compound in the method of generating phosphorescence
The invention relates to a method for generating phosphorescence in an organic compound. The organic compound must have a donor function group and a receptor function group, donor atoms have SP hybrid characteristics, and receptor atoms have SP hybrid characteristics. The donor atoms lose electrons in an SP hybrid state and transfer the electrons in the SP hybrid state to partially positively charged receptor atoms in an SP hybrid state in order to make a molecule be in an excited triplet state, and the excited molecule is resonated to make the receptor atoms become the SP hybrid state from the SP hybrid state in order to make an original donor become a receptor and an original receptor become a donor; and the donor atoms, which are receptor atoms in a ground state, lose the electrons in an SP hybrid state and transfer the electrons in the SP hybrid state to the receptor atoms in the SP hybrid state, and orbit-spin coupling is carried out again to make the molecule return to the ground state in order to generate phosphorescence. An organic phosphorescence generation mechanism is explicated in the invention for the first time, and scientific research personnel can easily synthesize organic molecules in a liquid or solid state and with visible phosphorescence in room temperature air under the guidance of the mechanism.
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(2017/08/24)

Two-point halogen bonding between 3,6-dihalopyromellitic diimides
The syntheses of 3,6-dichloro-, -dibromo-, and -diiodopyromellitic diimides - ACl, ABr, and AI, respectively - have been achieved. X-Ray crystallography of single crystals of ACl and ABr unveils the formation of extensive halogen-bonding networks in the solid state as a consequence of interactions between the lone pairs on the carbonyl oxygen atoms with the σ-holes of the halogen atoms. Further, the solid-state superstructure of diiodopyromellitic diimide is characterised by the formation of associated halogen-π dimers. The co-crystallisation of ACl or ABr with a 1,5-diaminonaphthalene derivative DN yields co-crystals of a mixed-stack charge-transfer (CT) complex which are supported by an expansive hydrogen-bonded network in addition to halogen-bonded belts that bring adjacent mixed-stacks into association with each other. 2,6-Dimethoxynaphthalene (DO) proved to be an effective CT complement to AI, yielding solvent-free co-crystals with superstructures which are comprised of a 1 - 2 ratio of AI to DO. This dimeric halogen-bonding motif is reminiscent of the formation of hydrogen-bonded dimers between carboxylic acids.
Cao, Dennis,Hong, Michael,Blackburn, Anthea K.,Liu, Zhichang,Holcroft, James M.,Stoddart, J. Fraser
p. 4242 - 4248
(2015/02/19)

Crown ether derivatised pyromellitic diimides
Pyromellitic diimide functionalised on the aromatic core with azacrown ethers have been synthesised and characterised by analytical methods including X-ray crystallography. Changes in their UV-vis spectra by the addition of metal salts have been investigated.
Sandanayake, Saman,Langford, Steven J.
p. 1264 - 1269
(2014/11/07)

Pyromellitic diimide-based donor-acceptor poly(phenylene ethynylene)s
A series of donor-acceptor poly(phenylene ethynylene)s (PPEs) with N,N′-dialkylpyromellitic diimide (PMDI) as electron acceptor and various donor units are reported. Optoelectronic properties were investigated by UV/vis absorption and electrochemical measurements, revealing constant LUMO energies (～-3.6 eV) across the series with HOMO energy levels governed by the donor monomers and optical band gaps from 2.30 to 1.50 eV. With a high volume fraction of solubilizing side chains, the polymers are soluble in common organic solvents, but solution NMR measurements and thermochromism in solution indicate aggregation due to additive intermolecular interactions between donor and acceptor units.
Guo, Xugang,Watson, Mark D.
scheme or table
p. 6711 - 6716
(2012/03/26)

Novel pyromellitic diimide-based macrocycle with a linear π-electronic system and bis(phenylethynyl)pyromellitic diimide: Syntheses, structures, photophysical properties, and redox characteristics
(Chemical Equation Presented) We report the syntheses, structures, photophysical properties, and redox characteristics of the [2 + 2] pyromellitic diimide-based macrocycle with a linear π-electronic system 2 as well as the 3,6-bis(phenylethynyl)pyromellitic diimide derivative 3. The interesting solid state structural properties of the clathrates of 3 with π-donors are also reported. The macrocycle 2 was synthesized by the direct cyclocondensation followed by the Sonogashira coupling reaction. X-ray crystallographic studies showed that the phenylacetylene moieties in 2 formed the intramolecular benzene dimer structures, and the bis(phenylethynyl)pyromellitic diimide moieties in both 2 and 3 were stacked in a parallel and slanted arrangement. Theoretical calculations for 2′ and 3 suggested the existence of electrostatic interactions between the bis(phenylethynyl)pyromellitic diimide moieties. The UV/vis spectral measurements and TDDFT calculations of 2, 2′, and/or 3 were performed to understand their electronic transitions. The fluorescence spectral measurements showed that 2 and 3 have visible fluorescence properties and 2 displays an excimer fluorescence at ca. 590 nm. The cyclic voltammetry measurements revealed that the electrostatic repulsion between the diimide moieties in 2 is greater than that in 1 according to the extension of the π-electronic systems. X-ray crystallography of the clathrates of 3 with various π-donors demonstrated the formation of the segregated donor-acceptor structures, indicating the strong aggregation ability of the bis(phenylethynyl)pyromellitic diimide moiety.
Kato, Shin-Ichiro,Nonaka, Yasuhiro,Shimasaki, Toshiaki,Goto, Kenta,Shinmyozu, Teruo
p. 4063 - 4075
(2008/09/20)