Structure and properties of new liquid crystalline cubane-1,4-dicarboxylic acid derivatives

G. Y. Bényei, I. Jalsovszky, C. Slugovc, G. Trimmel, G. Pelzl, A. Vajda, N. Éber, K. Fodor-Csorba

Research output: Contribution to journalArticle

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Abstract

New symmetrical esters of cubane-1,4-dicarboxylic acid have been prepared. These compounds have the bulky cubane moiety as the central building block. Five classes of derivative have been synthesized: (a) bis[(4-alkyl)phenyl]cubane-1, 4-dicarboxylates; (b) bis[(4-alkoxy)phenyl]cubane-1,4-dicarboxylates; (c) the two chiral derivatives bis(cholestenyl) cubane-1,4-dicarboxylate, and (S)-bis[4-(2-methylbutyloxycarbonyl)phenyl]cubane-1,4-dicarboxylate; (d) three members of the bis [4-(2,2-alkoxycarbonylvinyl)phenyl]cubane-1,4-dicarboxylates; and (e) bis[(4′-ethoxycarbonyl)-1,1′-biphenyl-4-yl]cubane-1,4- dicarboxylate. The shorter homologues of the alkoxyphenyl ester series exhibited a nematic (N) phase. No mesophase was observed for the pentyl derivative, while the higher homologues showed a smectic A (SmA) phase according to X-ray investigations. The 4-alkylphenyl and chiral derivatives showed only a melting point. The double swallow tailed bis[4-(2,2-alkoxy-carbonylvinyl)phenyl)]cubane- 1,4-dicarboxylates also exhibited no mesophase behaviour. On increasing the number of aromatic rings on both sides of the central cubane moiety, N and SmA phases appeared at higher temperatures. In binary mixtures of homologues of alkoxyphenylcubane esters, the temperature range of the SmA phase of the individual compounds became wider and enantiotropic in nature.

Original languageEnglish
Pages (from-to)197-205
Number of pages9
JournalLiquid Crystals
Volume32
Issue number2
DOIs
Publication statusPublished - Feb 2005

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cubane
Dicarboxylic Acids
dicarboxylic acids
Crystalline materials
Derivatives
Esters
Acids
Liquids
liquids
esters
Binary mixtures
Melting point
X rays
Temperature
binary mixtures
melting points
alkoxyl radical

ASJC Scopus subject areas

  • Condensed Matter Physics

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Structure and properties of new liquid crystalline cubane-1,4-dicarboxylic acid derivatives. / Bényei, G. Y.; Jalsovszky, I.; Slugovc, C.; Trimmel, G.; Pelzl, G.; Vajda, A.; Éber, N.; Fodor-Csorba, K.

In: Liquid Crystals, Vol. 32, No. 2, 02.2005, p. 197-205.

Research output: Contribution to journalArticle

Bényei, G. Y. ; Jalsovszky, I. ; Slugovc, C. ; Trimmel, G. ; Pelzl, G. ; Vajda, A. ; Éber, N. ; Fodor-Csorba, K. / Structure and properties of new liquid crystalline cubane-1,4-dicarboxylic acid derivatives. In: Liquid Crystals. 2005 ; Vol. 32, No. 2. pp. 197-205.
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N2 - New symmetrical esters of cubane-1,4-dicarboxylic acid have been prepared. These compounds have the bulky cubane moiety as the central building block. Five classes of derivative have been synthesized: (a) bis[(4-alkyl)phenyl]cubane-1, 4-dicarboxylates; (b) bis[(4-alkoxy)phenyl]cubane-1,4-dicarboxylates; (c) the two chiral derivatives bis(cholestenyl) cubane-1,4-dicarboxylate, and (S)-bis[4-(2-methylbutyloxycarbonyl)phenyl]cubane-1,4-dicarboxylate; (d) three members of the bis [4-(2,2-alkoxycarbonylvinyl)phenyl]cubane-1,4-dicarboxylates; and (e) bis[(4′-ethoxycarbonyl)-1,1′-biphenyl-4-yl]cubane-1,4- dicarboxylate. The shorter homologues of the alkoxyphenyl ester series exhibited a nematic (N) phase. No mesophase was observed for the pentyl derivative, while the higher homologues showed a smectic A (SmA) phase according to X-ray investigations. The 4-alkylphenyl and chiral derivatives showed only a melting point. The double swallow tailed bis[4-(2,2-alkoxy-carbonylvinyl)phenyl)]cubane- 1,4-dicarboxylates also exhibited no mesophase behaviour. On increasing the number of aromatic rings on both sides of the central cubane moiety, N and SmA phases appeared at higher temperatures. In binary mixtures of homologues of alkoxyphenylcubane esters, the temperature range of the SmA phase of the individual compounds became wider and enantiotropic in nature.

AB - New symmetrical esters of cubane-1,4-dicarboxylic acid have been prepared. These compounds have the bulky cubane moiety as the central building block. Five classes of derivative have been synthesized: (a) bis[(4-alkyl)phenyl]cubane-1, 4-dicarboxylates; (b) bis[(4-alkoxy)phenyl]cubane-1,4-dicarboxylates; (c) the two chiral derivatives bis(cholestenyl) cubane-1,4-dicarboxylate, and (S)-bis[4-(2-methylbutyloxycarbonyl)phenyl]cubane-1,4-dicarboxylate; (d) three members of the bis [4-(2,2-alkoxycarbonylvinyl)phenyl]cubane-1,4-dicarboxylates; and (e) bis[(4′-ethoxycarbonyl)-1,1′-biphenyl-4-yl]cubane-1,4- dicarboxylate. The shorter homologues of the alkoxyphenyl ester series exhibited a nematic (N) phase. No mesophase was observed for the pentyl derivative, while the higher homologues showed a smectic A (SmA) phase according to X-ray investigations. The 4-alkylphenyl and chiral derivatives showed only a melting point. The double swallow tailed bis[4-(2,2-alkoxy-carbonylvinyl)phenyl)]cubane- 1,4-dicarboxylates also exhibited no mesophase behaviour. On increasing the number of aromatic rings on both sides of the central cubane moiety, N and SmA phases appeared at higher temperatures. In binary mixtures of homologues of alkoxyphenylcubane esters, the temperature range of the SmA phase of the individual compounds became wider and enantiotropic in nature.

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