Liquid crystalline properties of salicylaldimine-based dimers: influence of terminal alkyl chain length and central part

Achten, Remko; Koudijs, A.; Karczmarzyk, Zbigniew; Marcelis, Antonius T. M.; Sudhölter, Ernst J. R.

doi:10.1080/02678290310001642531

Cited by 39 publications

(21 citation statements)

References 46 publications

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“…Our survey of the literature has demonstrated that this series of banana-shaped compounds are novel in the aspects of their molecular structures because they contain only three benzene rings [6][7][8][9][10][11][12][13][14].…”

Section: Resultsmentioning

confidence: 99%

“…For instance, banana-shaped compounds with different central cores, with different linkages in the wings of the molecules, and with varying lengths of the terminal alkyl tails have been extensively studied. A brief review of the literature reveals that most of the synthesised bananashaped LCs contain five benzene rings in their bent cores [1,2,6,11,12], and the remaining banana-shaped LCs are composed of either four benzene rings [13], six benzene rings [6,14,15] or seven benzene rings [6,16,17] in their bent cores. One question now emerges: could three-benzene-ring-containing bananashaped compounds form mesophases?…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and mesomorphic properties of three-benzene-ring-containing banana-shaped liquid crystals

Huang

2010

Liquid Crystals

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A homologous series of three-benzene-ring-containing banana-shaped compounds, N,N-bis(4-alkylcarbonyloxybenzylidene)benzene-1,3-diamine, were synthesised by esterifying aliphatic acids with the three-benzene-ring bent core 1,3-phenylene-bis(4-hydroxybenzylideneamine). As the number of carbon atoms in the aliphatic acids increased from 1 to 12, 12 novel banana-shaped compounds resulted with increasing lengths in their terminal tails. The mesomorphic properties of this homologous series of three-benzene-ring-containing banana-shaped compounds were characterised by means of polarised optical microscopy, differential scanning calorimetry, X-ray diffraction and electro-optical studies. Our results have demonstrated that this series of banana-shaped compounds can form mesophases, although each of their bent cores contains only three benzene rings.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis and mesomorphic properties of three-benzene-ring-containing banana-shaped liquid crystals

Huang

2010

Liquid Crystals

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“…The recent discovery of a ferroelectric switching behaviour in such compounds is particularly interesting (16) since in the early days it was believed that a central rigid aromatic part in the molecules was essential to obtain such mesophase types. The B-phases have so far been reported for dimeric compounds having benzylideneaniline (16), salicylideneaniline (17) or benzoyloxysalicyl (16) mesogenic cores connected with a methylene spacer via ester (17,18) or imine (18) linkages.…”

Section: Introductionmentioning

confidence: 99%

Odd–even effect in biphenyl‐based symmetrical dimers with methylene spacer – evidence of the B4 phase

et al. 2008

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A series of 4-decyloxy-49-hydroxybiphenyl esters of a,v-alkanedicarboxylic acids containing two mesogenic units connected by a methylene spacer was synthesized. The mesogenic properties of the compounds were investigated by polarising optical microscopy, differential scanning calorimetry and X-ray diffraction methods. A strong influence of the spacer length and its parity on the mesomorphic properties was found. A dramatic odd-even effect was observed for the clearing temperatures and entropies. Compounds with an even number of carbon atoms in the methylene spacer formed tilted smectic phases, whereas compounds with an odd number of carbon atoms in the spacer exhibited the B4 phase, characteristic of bent-shaped molecules.

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“…In the case of an odd-numbered spacer these dimers exhibit a bent shape and form nematic, columnar nematic, smectic and columnar phases. Columnar phases were not found for the dimers having even-numbered spacers, because these molecules are more linear [ 23 – 27 ]. Interestingly, for a nonsymmetric chiral dimer the reentrant-phase behaviour SmA–SmA b –SmA was reported [ 28 ].…”

Section: Introductionmentioning

confidence: 99%

Laterally substituted symmetric and nonsymmetric salicylideneimine-based bent-core mesogens

Findeisen-Tandel¹,

Weißflog²,

Baumeister³

et al. 2012

Beilstein J. Org. Chem.

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SummaryBent-core mesogens have gained considerable importance due to their ability to form new mesophases with unusual properties. Relationships between the chemical structure of bent-core molecules and the type and physical properties of the formed mesophases are relatively unknown in detail and differ strongly from those known for calamitic liquid crystals. In this paper symmetric and nonsymmetric five-ring salicylideneaniline-based bent-core mesogens are presented, and the effect of lateral substituents attached at the outer phenyl rings (F, Cl, Br) or the central phenyl ring (CH3) on the liquid-crystalline behaviour and on the physical properties is studied. Corresponding benzylideneaniline-based compounds were additionally prepared in order to study the influence of the intramolecular hydrogen bond. The occurring mesophases were investigated by differential scanning calorimetry, polarising microscopy, X-ray diffraction and dielectric and electro-optical measurements. The paper reports on new findings with respect to the structure–property relationships of bent-core mesogens. On one hand, the disruptive effect of laterally substituted halogen atoms, F, Cl and Br, on the mesophase behaviour of three isomeric series was much lower than expected. On the other hand, an increase of the clearing temperature by 34 K was observed, caused by small lateral substituents. The electro-optical behaviour, especially the type of polar switching and corresponding molecular movements, is sensitive to variations in the molecular structure.

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Liquid crystalline properties of salicylaldimine-based dimers: influence of terminal alkyl chain length and central part

Cited by 39 publications

References 46 publications

Synthesis and mesomorphic properties of three-benzene-ring-containing banana-shaped liquid crystals

Synthesis and mesomorphic properties of three-benzene-ring-containing banana-shaped liquid crystals

Odd–even effect in biphenyl‐based symmetrical dimers with methylene spacer – evidence of the B4 phase

Laterally substituted symmetric and nonsymmetric salicylideneimine-based bent-core mesogens

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