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Plank-Shaped Column-Forming Mesogens with Substituents on One Side Only

Abstract : Prolonged glyoxylation of pyrenyl-1-glyoxylic acid ethyl ester leads to a mixture of isomers with polar pyreny- lene-1,8-diglyoxylic acid as the main product, whereas the centrosymmetric 1,6-isomer is obtained in good yield from the corresponding dibromopyrene. Perkin condensations fol- lowed by Pd-catalyzed cyclizations lead to isomeric dinaph- thopyrene-tetracarboxdiimides that self-assemble into col- umnar liquid crystals of hexagonal and rectangular symme- try, of which the rectangular mesophases have unusually elongated unit cells. The cisoid diimides with both alkylimide substituents on the same side of the oblong arene system show a much greater tendency to self-assemble into fluid stacks of disks than their centrosymmetric isomers. With rac- emically branched alkyl substituents, uniform vertical surface alignment of the columns in the high-temperature hexago- nal mesophase is resilient to cycling through the lower-tem- perature rectangular and crystalline phases.
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Submitted on : Tuesday, February 2, 2021 - 9:41:23 AM
Last modification on : Thursday, February 11, 2021 - 8:46:24 AM
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Edivandro Girotto, Marli Ferreira, Parantap Sarkar, Ahmed Bentaleb, Elisabeth A. Hillard, et al.. Plank-Shaped Column-Forming Mesogens with Substituents on One Side Only. Chemistry - A European Journal, Wiley-VCH Verlag, 2015, 21, pp. 7603-7610. ⟨10.1002/chem.201500048⟩. ⟨hal-01153866⟩



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