Homologous series of liquid-crystalline metal free and copper octa-n-alkoxyphthalocyanines

Hexaarylbenzene (HAB) derivatives are versatile aromatic systems playing a significant role as chromophores, liquid crystalline materials, molecular receptors, redox materials, organic light-emitting diodes and photochemical switches. Statistical synthesis of simple symmetrical HABs is known via low-yielding cyclotrimerization or Diels-Alder reactions. By contrast, the synthesis of more complex, asymmetrical systems, and without involvement of statistical steps, remains an unsolved problem. Here we present a generally applicable synthetic strategy to access asymmetrical HAB via an atom-economical and high-yielding metal-free four-step domino reaction using nitrostyrenes and α,α-dicyanoolefins as easily available starting materials. Resulting domino product – functionalized triarylbenzene (TAB) - can be used as a key starting compound to furnish asymmetrically substituted hexaarylbenzenes in high overall yield and without involvement of statistical steps. This straightforward domino process represents a distinct approach to creating diverse and still unexplored HAB scaffolds, containing six different aromatic rings around central benzene core.

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The scope and limitations of liquid-crystalline behaviour in monosaccharide amphiphiles Comparison of the thermal behaviour of several homologous series of D-glucose derived compounds with an amino-linked alkyl chain

Liquid Crystals ◽

10.1080/02678299008047334 ◽

1990 ◽

Vol 8 (1) ◽

pp. 109-121 ◽

Cited By ~ 38

Author(s):

Henk A. Van Doren ◽

Ralph Van Der Geest ◽

Cornelis F. De Ruijter ◽

Richard M. Kellogg ◽

Hans Wynberg

Keyword(s):

Thermal Behaviour ◽

Homologous Series ◽

Liquid Crystalline ◽

Alkyl Chain

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Homologous Series of Liquid Crystalline Steroidal Lipids

Journal of Physical and Chemical Reference Data ◽

10.1063/1.556007 ◽

1997 ◽

Vol 26 (2) ◽

pp. 291-333 ◽

Cited By ~ 19

Author(s):

Thies Thiemann ◽

Volkmar Vill

Keyword(s):

Homologous Series ◽

Liquid Crystalline

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Raman scattering studies of order parameters in liquid crystalline dimers exhibiting the nematic and twist-bend nematic phases

Journal of Materials Chemistry C ◽

10.1039/c5tc02174j ◽

2015 ◽

Vol 3 (38) ◽

pp. 10007-10016 ◽

Cited By ~ 50

Author(s):

Zhaopeng Zhang ◽

Vitaly P. Panov ◽

Mamatha Nagaraj ◽

Richard J. Mandle ◽

John W. Goodby ◽

...

Keyword(s):

Raman Spectroscopy ◽

Raman Scattering ◽

Homologous Series ◽

Liquid Crystalline ◽

Orientational Order ◽

Order Parameters ◽

Polarized Raman Spectroscopy ◽

Nematic Phases ◽

Polarized Raman

The work deduces orientational order parameters in the nematic and twist-bend nematic phases. An homologous series of dimers is studied using Polarized Raman Spectroscopy.

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