Hong Cheu Lin

Synthesis of new schiff base ester liquid crystals with a benzothiazole core

A series of new calamitic liquid crystals, 6-methoxy-2-(4-alkanoyloxybenzylidenamino)benzothiazoles, comprising a benzothiazole core, terminal methoxy group and a Schiff base linkage were synthesised and characterised. This series comprises 12 members wherein members differ by the length of the alkanoyloxy chain (C n-1H2n-1COO-, where n = 2–8, 10, 12, 14, 16, 18). Their mesomorphic properties were studied by using differential scanning calorimetry, optical polarising microscopy and powder X-ray diffraction techniques. The short chain derivatives (n = 2 and 3) were non-mesogenic compounds, while an enantiotropic nematic phase was present throughout the remaining members of the series. The smectic C phase emerged from the decanoyloxy derivative onwards.

Mesogenic Schiff base esters with benzothiazole core: synthesis and phase transition studies

A series of new rod-shaped mesomorphic compounds, 6-ethoxy-2-(4-alkanoyloxybenzylidenamino)benzothiazoles, consisting of a 2,6-disubstituted benzothiazole core and a Schiff base central linkage, were synthesized and their structures were ascertained via elemental analysis and spectroscopic techniques. Their mesomorphic properties were studied using differential scanning calorimetry (DSC), polarized optical microscopy (POM) and X-ray diffraction (XRD) analysis. All compounds showed enantiotropic mesomorphism. Whilst the lower members of the series, hexanoyloxy and octanoyloxy derivatives exhibited nematic phase, the higher members (decanoyloxy, dodecanoyloxy, tetradecanoyloxy, hexadecanoyloxy and octadecanoyloxy derivatives) exhibited nematic and smectic C phases.

Synthesis and Mesomorphic Properties of 6-Methoxy- and 6-Ethoxy-2-(2-Hydroxy-4-Alkanoyloxybenzylidenamino)Benzothiazoles

Two new series of Schiff base thermotropic liquid crystals, 6-methoxy-2-(2-hydroxy-4-alkanoyloxybenzylidenamino)benzothiazoles and 6-ethoxy-2-(2-hydroxy-4-alkanoyloxybenzylidenamino)benzothiazoles, comprising different terminal groups, a methoxyl and ethoxyl group, respectively, were synthesized. Structural elucidation was carried out using elemental analysis and spectroscopic techniques such as Fourier transform infrared (FTIR), 1H and 13C nuclear magnetic resources (NMR), and mass spectrometry. The mesomorphic properties and thermal stabilities of the title compounds were studied by using differential scanning calorimetry, optical polarizing microscopy, and thermogravimetric analysis. No liquid-crystal phases were observed for the short-chain members (n = 2 and 3) in both series, and the remaining members all exhibited nematic phase with Schlieren or marble-like textures. Effects of the lateral hydroxyl group, terminal group, and the length of the terminal alkanoyloxy chain on the mesomorphic properties are discussed. Structure-property relationships were established upon comparison with other structurally related compounds.

Synthesis and phase transition behaviours of laterally substituted liquid crystals containing methylhydroquinone: emerging of smectic C phase for higher homologues

ABSTRACT A series of laterally substituted low-molar-mass liquid crystals with molecular geometry were constructed with three phenyl rings bridged through ester central groups as the rigid core and a lateral methyl group as the flexible part of a molecule, with a view to understanding and establishing the effect of molecular structure on liquid crystal behaviour. Low-molar-mass mesogens known as 1,4-bis[(4′-n-alkyloxybenzoyl)oxy]toluene with different number of carbon (n) at the alkyl chain have been prepared. Their molecular structures were proposed via physical measurements and spectroscopic techniques. Mesomorphic properties were studied by using differential scanning calorimetry, optical polarizing microscopy and powder X-ray diffraction techniques. The results showed that the melting points as well as the clearing temperatures decreased upon lengthening of the terminal alkyloxy chain lengths. Members with the shorter chain (n = 2–10) exhibited nematic phase. As for higher homologues, members with n = 12, 14, 16 and 18 showed polymorphism, whereby these compounds displayed both smectic and nematic properties.

Liquid crystalline non-linear S-shaped oligomers consisting of azobenzene and biphenylene units: synthesis, characterisation and influence of central spacer

ABSTRACT A series of non-linear S-shaped liquid crystal oligomers wherein the molecule consists of biphenylene moiety as a central core unit and two symmetrical side arms azobenzene moieties joined to catechol as a linkage group have been successfully synthesised and characterised. The members in this series possess different inner spacer with carbon number n ranging from 4 to 9 while the outer spacer length located in azobenzene moieties are remains unaltered. The members with even parity exhibit monotropic phase, whereas homologues with odd parity display enantiotropic phase. The appearance of nematic, smectic A and smectic B phases was validated with texture observation under polarised light and X-ray diffraction (XRD). The XRD study on the S-shaped oligomer indicates that the arrangement of smectic phase exists as an intercalated structure. The S-shaped oligomer shows photoisomerisation properties in solution whereby the trans to cis isomerisation for this molecule is accomplished 1140 s, whereas reverse process under thermal back reaction occurred in 4620 min. Graphical Abstract

Influence of terminal substituent on non-linear S-shaped oligomers consisting of azobenzene moieties at the peripheral arm: Synthesis, characterisation and phase transition behaviour

ABSTRACT A series of symmetrical S-shaped mesogens based on 4,4′-bis-(6-bromohexyloxy)biphenyl as a central unit containing two 2-{6-[4-(4-substitutedphenylazo)phenoxy]hexyloxy}phenol as side-chain groups has been successfully synthesised. The terminal substituent was varied from halogen (X = F, Cl, Br and I) to non-halogen (X = C2H5 and OC2H5). The oligomers with C2H5 and OC2H5 substituents exhibit predominantly the monotropic nematic (N) phase. The OC2H5-containing derivatives possess long-range stability of N phase than its C2H5-containing analogue in which it has small range of N phase stability. As for halogen-containing analogues, oligomer with F exhibits monotropic N phase whilst oligomers with Cl and Br exhibit monotropic N and smectic A (SmA) phases. In addition, homologue with Br shows additional phase which is smectic B (SmB) phase upon further cooling. However, the oligomers in which F, Cl and Br were substituted by I exhibits purely monotropic SmA and SmB phases. X-ray diffraction measurements reveal that the smectic phase is inclined to the monolayer structure. GRAPHICAL ABSTRACT