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

Psutka, Katie M.; Williams, Joshua; Paquette, Joseph A.; Calderon, Oliver; Bozek, Kevin J. A.; Williams, Vance E.; Malý, Karel

doi:10.1002/ejoc.201403504

Cited by 12 publications

(15 citation statements)

References 39 publications

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“…4,5‐Dibromophthalonitrile and 6,7‐dibromonaphthalene‐2,3‐dicarbonitrile were synthesized according to literature procedures. A Monowave 300 reactor from Anton Paar with an external IR temperature sensor was used for microwave reactions.…”

Section: Methodsmentioning

confidence: 99%

Dicyano‐Substituted Diazaacenes

Müller

Beglaryan

Koser

et al. 2017

Chemistry A European J

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Herein, we report the synthesis, spectroscopic, and structural properties of novel 2,3-dicyano-substituted azaacenes containing three to six annelated rings as a framework. The targets were prepared by Pd-catalyzed coupling of diamino-bis(tri-isopropylsilylethynyl)benzene, -naphthalene, and -anthracene with either 4,5-dibromophthalonitrile or 6,7-dibromonaphthalene-2,3-dicarbonitrile into the respective N,N'-dihydrodiazaacenes. Oxidation with MnO or PbO furnishes the dicyano-substituted diazaacenes in reasonable to good yields. An exception is the diazahexacene, where the N,N'-dihydrodiazaacene is difficult to oxidize. Most of the targets could be crystallized and pack in isolated pairs, stacks, and brick-wall motifs. The n-type behavior of these molecules was illustrated in a proof-of-concept organic field-effect transistor, showing mobilities up to 7×10 cm V s .

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Section: Methodsmentioning

confidence: 99%

Dicyano‐Substituted Diazaacenes

Müller

Beglaryan

Koser

et al. 2017

Chemistry A European J

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Section: Reviewmentioning

confidence: 99%

“…Then, an oxidative cyclization of 138 in the presence of FeCl 3 afforded dibenzo[ a , c ]anthracenes 139a and 139b in moderate yields (58–68%). On the other hand, they obtained dibenzo[ a , c ]anthracenes 139c – e in low to moderate yields (15–54%) when they used DDQ/MeSO 3 H instead of FeCl 3 [ 66 ].…”

Section: Reviewmentioning

confidence: 99%

“…In 2015, Maly and co-workers reported a two-step synthetic route to obtain substituted 2,3,5,6-tetraalkoxydibenzo[a,c]anthracenes 139 bearing H, CN, or OMe groups at positions 11 and 12, to study their liquid crystalline properties (Scheme 32) [66]. Their methodology started with a Suzuki coupling reaction of substituted dibromonaphthalenes 136 and boronate diesters 137, to provide the corresponding 2,3- In a study published in 2018, de Koning and co-workers reported a new methodology to synthesize the benzo[a]anthracene skeleton of angucycline derivatives 146 by using a multistep strategy based on Suzuki-Miyaura, isomerization, and ringclosing metathesis reactions (Scheme 33) [67].…”

Section: Intramolecular Cyclizationmentioning

confidence: 99%

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Recent advances in the syntheses of anthracene derivatives

Baviera

Donate

2021

Beilstein J. Org. Chem.

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Anthracene and anthracene derivatives have been extensively studied over the years because of their interesting photophysical, photochemical, and biological properties. They are currently the subject of research in several areas, which investigate their use in the biological field and their application in OLEDs, OFETs, polymeric materials, solar cells, and many other organic materials. Their synthesis remains challenging, but some important preparative methods have been reported, especially in the last decade. This review presents an update of the recent strategies that have been employed to prepare anthracene derivatives. It encompasses papers published over the last twelve years (2008–2020) and focuses on direct and indirect methods to construct anthracene and anthraquinone frameworks.

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

Cited by 12 publications

References 39 publications

Dicyano‐Substituted Diazaacenes

Dicyano‐Substituted Diazaacenes

Recent advances in the syntheses of anthracene derivatives

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

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