Synthesis and Mesomorphic Properties of Novel Dibenz[<i>a</i>,<i>c</i>]anthracenedicarboximides

Psutka, Katie M.; Bozek, Kevin J. A.; Malý, Karel

doi:10.1021/ol502678m

Cited by 18 publications

(11 citation statements)

References 35 publications

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“…The reaction proceeds by an iodide-induced 1,4-elimination of bromine to generate the corresponding o-quinodimethane, which undergoes a Diels-Alder reaction with fumaronitrile, followed by rearomatization through elimination of HBr. Suzuki cross-coupling of 8-10 with 7 yielded corresponding 2,3-diphenylnaphthalenes (11)(12)(13) in moderate to good yields. Suzuki cross-coupling of 8-10 with 7 yielded corresponding 2,3-diphenylnaphthalenes (11)(12)(13) in moderate to good yields.…”

Section: Resultsmentioning

confidence: 99%

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Synthesis of Substituted Dibenz[a,c]anthracenes and an Investigation of Their Liquid‐Crystalline Properties

et al. 2015

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We report the synthesis of a series of 2,3,5,6‐tetraalkoxydibenz[a,c]anthracenes bearing substituents (H, OCH3, or CN) in the 11‐ and 12‐positions and an investigation of their liquid‐crystalline properties. The synthesis involved Suzuki coupling of the appropriate dibromonaphthalene and boronate ester, followed by an oxidative cyclization. Compounds 4 and 5, bearing OCH3 and H, respectively, do not exhibit any liquid‐crystalline properties. In contrast, compounds 6a–c, bearing cyano groups, assemble into columnar mesophases, suggesting that electron‐withdrawing groups are important for promoting columnar mesophase assembly. Analysis of the XRD revealed that compound 6b exhibits a columnar hexagonal phase, whereas compounds 6a and 6c exhibit columnar rectangular phases. The XRD data of 6a and 6b also show reflections that are consistent with antiparallel dimers within the columnar stacks, and intercolumnar spacings suggest that molecules are tilted within the columns.

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Section: Resultsmentioning

confidence: 99%

“…[10] We have also demonstrated that the dibenzanthracenedicarboximide derivatives exhibit columnar hexagonal phases over broad temperature ranges. [12] These studies underscore the remarkable sensitivity to even minor structural changes when considering self-assembly of these compounds.…”

Section: Introductionmentioning

confidence: 98%

Synthesis of Substituted Dibenz[a,c]anthracenes and an Investigation of Their Liquid‐Crystalline Properties

et al. 2015

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“…Solche Systeme sind von Interesse als Spintronikmaterialien. Die Synthese von neuartigen diskotischen Mesogenen (16) mit einem Dibenz[a,c]anthracenedicarboximidkern präsentieren Maly et al15…”

Section: Flüssigkristalleunclassified

Organische Chemie 2014

Beifuss¹,

Lehmann²,

Krueger³

et al. 2015

Nachr Chem

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“…2-7), where the PAH core is extended as compared to the corresponding triphenylenes, have until recently received relatively little attention as potential columnar liquid crystalline materials. 11,[19][20][21] Williams and coworkers were the first to report an example of a dibenzanthracene derivative (3) exhibiting a columnar hexagonal mesophase. 11 The mesophase range of 3 was much broader than that of the corresponding triphenylene, suggesting that extending the aromatic core stabilizes the mesophase through improved π-stacking interactions.…”

Section: Introductionmentioning

confidence: 99%

Probing the structural features that influence the mesomorphic properties of substituted dibenz[a,c]anthracenes

et al. 2017

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We report the synthesis and mesophase characterization of a series of novel hexaalkoxydibenzanthracenes in order to probe the effect of side-chain length variation and substituents on the mesophase temperature range.A series of hexaalkoxydibenz [a,c]anthracenes (2a-i) with varying chain lengths were prepared by Suzuki coupling of the appropriate boronate ester with the corresponding dialkoxydibromonaphthalenes, followed by oxidative cyclization. Compounds 2a-i were also brominated in the 10 and 13-positions to yield the corresponding dibromo series 4a-i.While none of the compounds 2a-i exhibited columnar mesophases, all of the compounds in series 4a-i did exhibit columnar phases over broad temperature ranges. To further investigate the effect of substituents on the mesomorphic properties of hexaalkozydibenzanthracenes, we also prepared iodo-substituted 8, nitro-substituted 9, and amino-substituted 10. A comparison of the mesophase temperature range with previously reported compounds 3-7 shows that electron-withdrawing groups promote the formation of stable mesophases. However, our results also suggest that the substituents affect mesophase stability by participating in intermolecular contacts within the columnar stacks of the mesophase.

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Synthesis and Mesomorphic Properties of Novel Dibenz[a,c]anthracenedicarboximides

Cited by 18 publications

References 35 publications

Synthesis of Substituted Dibenz[a,c]anthracenes and an Investigation of Their Liquid‐Crystalline Properties

Synthesis of Substituted Dibenz[a,c]anthracenes and an Investigation of Their Liquid‐Crystalline Properties

Organische Chemie 2014

Probing the structural features that influence the mesomorphic properties of substituted dibenz[a,c]anthracenes

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