Synthesis of Extended Linear Aromatics Using Tandem Diels-Alder Aromatization Reactions

Morris, J. Larry; Becker, Calvin L.; Fronczek, Frank R.; Daly, William H.; McLaughlin, Mark L.

doi:10.1021/jo00100a065

Cited by 58 publications

(38 citation statements)

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“…H 4 ata and azpy were synthesized according to the reported methods. 13,14 Elemental analyses (C, H, and N) spectra for the powdered solid samples were measured on a Varian Cary Eclipse fluorescence spectrophotometer and all the measurements were carried out under the same experimental conditions. The X-ray powder diffraction spectra (XRPD) were recorded on a Rigaku D/Max-2500 diffractometer at 40 kV, 100 mA for a Cutarget tube and a graphite monochromator.…”

Section: Methodsmentioning

confidence: 99%

Zn^II Coordination Poylmers Based on 2,3,6,7-Anthracenetetracarboxylic Acid: Synthesis, Structures, and Luminescence Properties

Chang

Zhang

et al. 2009

Crystal Growth & Design

104

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In our efforts to investigate polydentate ligands bearing bulky backbones, we used a bulky ligand, 2,3,6,7-anthracenetetracarboxylic acid (H 4 ata), to react with Zn II ions under different conditions, yielding four new coordination polymers, {[Zn(ata) 0.5 (DMF)(H 2 O)] 3 DMF 3 H 2 O} n (1), {[Zn(ata) 0.5 (4,4 0 -bipy) 0.5 (DMF)] 3 DMF} n (2), {[Zn(ata) 0.5 (azpy) 0.5 (DMF)] 3 DMF} n (3), and {[Zn(ata) 0.5 (4,4 0 -bipy)(DMAC)] 3 (DMA) 0.5 } n (4) (DMF = N,N-dimethylformamide, 4,4 0 -bipy = 4,4 0 -bipyridine, azpy=4,4 0 -azopyridine, DMAC=N,N-dimethylacetamide, DMA=dimethylamine), which were characterized by IR and single crystal X-ray diffraction. Complex 1 forms a two-dimensional (2D) network with (4,4) topology assembled by ata 4-ligands and Zn II ions. Complexes 2 and 3 are three-dimensional (3D) frameworks with {8 3 } 2 {8 5 ;10} topology containing infinite 2D networks pillared by 4,4 0 -bipy and azpy, respectively. Complex 4 takes a 2D structure with (4,4) net containing infinite onedimensional chains constructed by Zn II ions with 4,4 0 -bipy and ata 4-ligands. These results show that the reaction of 2,3,6,7-anthracenetetracarboxylic acid with Zn II in DMF tends to yield a layer structure which could be pillared by bipyridine-like ligands into 3D frameworks, and the final structure of the coordination polymer is greatly influenced by the solvent. Furthermore, the luminescence properties of 1-4 were studied in the solid state at room temperature.

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Section: Methodsmentioning

confidence: 99%

Zn^II Coordination Poylmers Based on 2,3,6,7-Anthracenetetracarboxylic Acid: Synthesis, Structures, and Luminescence Properties

Chang

Zhang

et al. 2009

Crystal Growth & Design

104

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“…Instead, a bicyclic structure ( 9 ) was the only product isolated. McLaughlin et al6 also used a tandem reaction of this type to synthesize the diimide of 2,3,7,8‐anthracenetetracarboxylic acid dianhydride.…”

Section: Introductionmentioning

confidence: 99%

Fluorescent poly(aryl ether)s containing benzo[g]phthalazine and benzo[g]isoquinoline moieties

Kang

Hlil

Hay

2004

J. Polym. Sci. A Polym. Chem.

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2,3‐Bis(4‐fluorobenzoyl)naphthalene was synthesized, and poly(aryl ether)s were prepared through a reaction with various bisphenols in the solvent N,N‐dimethylacetamide in the presence of potassium carbonate. Through a reaction with hydrazine or benzylamine, the corresponding benzo[g]phthalazine or benz[g]isoquinoline was formed. The conversion into heterocyclic structures resulted in a significant straightening of the chains, and the glass‐transition temperatures, inherent viscosities, and apparent molecular weights from size exclusion chromatography were significantly increased, whereas the solubilities decreased. The diketone‐containing polymers were colorless, and the benzo[g]phthalazine‐ and benz[g]isoquinoline‐containing polymers were yellow. The diketone polymers showed strong UV absorption maxima up to 350 nm, with fluorescence emission maxima around 475 nm. The heterocyclic polymers had broad absorptions up to around 450 nm, with strong emission maxima around 550 nm. © 2004 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 42: 5745–5753, 2004

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“…5,6 Anthracene-2,3:6,7-bisimides (ABIs) are also promising candidates for the construction of various functional molecules. 7 ABI derivatives with 1,5-diphenyl and 9,10-dicyano groups have been utilized as chemical sensors 8 and OFET materials, 9 respectively. In general, the electronic properties of anthracene moieties are considerably influenced by substitution with arylethynyl groups.…”

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confidence: 99%

“…Durene was first brominated to afford compound 5, 13 which was then further brominated by irradiation with bromine to give heptabromide 6 in a manner similar to a previously known method. 7,9 The regioselectivity of the bromination was confirmed by X-ray structural analysis [see the Supporting Information (SI)].…”

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confidence: 99%

Introduction of an Arylethynyl Group onto an Anthracene Bisimide Core for Molecular Design of New π-Conjugated Compounds

2013

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Novel ethynylated anthracene bisimide (ABI) derivatives were synthesized by Sonogashira and Stille couplings, and the electronic spectra of the new compounds were compared with those of molecules with related structures. The absorption spectrum and the electrochemical data of the ABI with a 9-anthrylethynyl group suggested weak electronic interactions between the donor anthracene unit and the acceptor ABI unit.As electron-deficient moieties, aromatic bisimides have been attractive building units for the molecular design of new π-conjugated functional materials.1 In particular, perylene bisimides and naphthalene bisimides have been extensively applied to the development of new organic devices 2 such as organic light-emitting diodes, 3 organic field-effect transistors (OFETs), 4 and organic photovoltaics. 5,6 Anthracene-2,3:6,7-bisimides (ABIs) are also promising candidates for the construction of various functional molecules.7 ABI derivatives with 1,5-diphenyl and 9,10-dicyano groups have been utilized as chemical sensors 8 and OFET materials, 9 respectively. In general, the electronic properties of anthracene moieties are considerably influenced by substitution with arylethynyl groups.10 However, to the best of our knowledge, no ABI derivatives having acetylene substituents have yet been reported in the literature. Recently, we reported that a donoracceptor array consisting of a perylene bisimide core and a 9-anthrylethynyl group showed interesting spectroscopic properties due to charge-transfer interactions.11 Therefore, we designed a new donoracceptortype ABI derivative 1 having a 9-anthrylethynyl group at the 9 position, in which the ABI unit serves as a terminal acceptor unit (Figure 1). We herein report the synthesis and spectroscopic data of ABI derivative 1 and its analogue 2 and the results of a comparison of their photophysical and electrochemical properties with those of the related compounds 3 12 and 4 9 in order to evaluate the π-conjugation.For the synthesis of the target ABI derivatives, 9-Br-ABI 8 was used as a key intermediate for ethynylation by crosscoupling reactions. This precursor was prepared by the Diels Alder approach, as shown in Scheme 1. Durene was first brominated to afford compound 5, 13 which was then further brominated by irradiation with bromine to give heptabromide 6 in a manner similar to a previously known method.7,9 The regioselectivity of the bromination was confirmed by X-ray structural analysis [see the Supporting Information (SI)].14 Reaction of 6 with N-octylmaleimide in the presence of NaI afforded the DielsAlder adduct 7 as a mixture of diastereomers, which was then aromatized by radical bromination followed by elimination. The series of reactions gave compound 8 in 26% overall yield from 6.The Sonogashira coupling of 8 with 9-ethynylanthracene 15 in a conventional manner gave compound 1 as a red solid in 95% yield, while the Stille coupling of bromide 8 with bis(tributylstannyl)ethyne in the presence of [Pd(PPh 3 ) 4 ], as well as LiCl as additive in dioxane gave comp...

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Synthesis of Extended Linear Aromatics Using Tandem Diels-Alder Aromatization Reactions

Cited by 58 publications

References 0 publications

Zn^II Coordination Poylmers Based on 2,3,6,7-Anthracenetetracarboxylic Acid: Synthesis, Structures, and Luminescence Properties

Zn^II Coordination Poylmers Based on 2,3,6,7-Anthracenetetracarboxylic Acid: Synthesis, Structures, and Luminescence Properties

Fluorescent poly(aryl ether)s containing benzo[g]phthalazine and benzo[g]isoquinoline moieties

Introduction of an Arylethynyl Group onto an Anthracene Bisimide Core for Molecular Design of New π-Conjugated Compounds

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Synthesis of Extended Linear Aromatics Using Tandem Diels-Alder Aromatization Reactions

Cited by 58 publications

References 0 publications

ZnII Coordination Poylmers Based on 2,3,6,7-Anthracenetetracarboxylic Acid: Synthesis, Structures, and Luminescence Properties

ZnII Coordination Poylmers Based on 2,3,6,7-Anthracenetetracarboxylic Acid: Synthesis, Structures, and Luminescence Properties

Fluorescent poly(aryl ether)s containing benzo[g]phthalazine and benzo[g]isoquinoline moieties

Introduction of an Arylethynyl Group onto an Anthracene Bisimide Core for Molecular Design of New π-Conjugated Compounds

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Product

Resources

About

Zn^II Coordination Poylmers Based on 2,3,6,7-Anthracenetetracarboxylic Acid: Synthesis, Structures, and Luminescence Properties

Zn^II Coordination Poylmers Based on 2,3,6,7-Anthracenetetracarboxylic Acid: Synthesis, Structures, and Luminescence Properties