Amide, urea and thiourea-containing triphenylene derivatives: influence of H-bonding on mesomorphic properties

I. Paraschiv, A. Tomkinson, M. Giesbers, E.J.R. Sudhölter, H. Zuilhof, A.T.M. Marcelis

Research output: Contribution to journalArticleAcademicpeer-review

32 Citations (Scopus)

Abstract

The synthesis and thermotropic properties are reported for a series of hexaalkoxytriphenylenes that contain an amide, urea or thiourea group in one of their alkoxy tails. The intermolecular hydrogen bonding abilities of these molecules have a disturbing influence on the formation and stability of the columnar liquid crystalline phases. The stronger the hydrogen bonding the more the liquid crystallinity is suppressed, probably due to disturbance of the - stacking of the triphenylene discs. As a direct result, urea- and amide-containing triphenylene derivatives are not liquid crystalline, but several thiourea derivatives show hexagonal columnar mesophases.
LanguageEnglish
Pages1029-1038
JournalLiquid Crystals
Volume34
Issue number9
DOIs
Publication statusPublished - 2007

Fingerprint

Thiourea
Thioureas
thioureas
ureas
Amides
Urea
amides
Derivatives
Hydrogen bonds
Liquids
liquids
Crystalline materials
hydrogen
crystallinity
disturbances
Molecules
synthesis
triphenylene
molecules

Keywords

  • discotic liquid-crystals
  • charge-transport
  • organic-solvents
  • peripheral chains
  • self-organization
  • bisurea compounds
  • hydrogen-bonds
  • columnar
  • molecules
  • state

Cite this

Paraschiv, I. ; Tomkinson, A. ; Giesbers, M. ; Sudhölter, E.J.R. ; Zuilhof, H. ; Marcelis, A.T.M. / Amide, urea and thiourea-containing triphenylene derivatives: influence of H-bonding on mesomorphic properties. In: Liquid Crystals. 2007 ; Vol. 34, No. 9. pp. 1029-1038.
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Amide, urea and thiourea-containing triphenylene derivatives: influence of H-bonding on mesomorphic properties. / Paraschiv, I.; Tomkinson, A.; Giesbers, M.; Sudhölter, E.J.R.; Zuilhof, H.; Marcelis, A.T.M.

In: Liquid Crystals, Vol. 34, No. 9, 2007, p. 1029-1038.

Research output: Contribution to journalArticleAcademicpeer-review

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T1 - Amide, urea and thiourea-containing triphenylene derivatives: influence of H-bonding on mesomorphic properties

AU - Paraschiv, I.

AU - Tomkinson, A.

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AU - Sudhölter, E.J.R.

AU - Zuilhof, H.

AU - Marcelis, A.T.M.

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AB - The synthesis and thermotropic properties are reported for a series of hexaalkoxytriphenylenes that contain an amide, urea or thiourea group in one of their alkoxy tails. The intermolecular hydrogen bonding abilities of these molecules have a disturbing influence on the formation and stability of the columnar liquid crystalline phases. The stronger the hydrogen bonding the more the liquid crystallinity is suppressed, probably due to disturbance of the - stacking of the triphenylene discs. As a direct result, urea- and amide-containing triphenylene derivatives are not liquid crystalline, but several thiourea derivatives show hexagonal columnar mesophases.

KW - discotic liquid-crystals

KW - charge-transport

KW - organic-solvents

KW - peripheral chains

KW - self-organization

KW - bisurea compounds

KW - hydrogen-bonds

KW - columnar

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KW - state

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