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Synthesis of Branched-Chain Alkyl Glucosides and Their Liquid Crystal Behaviour

Rauzah Hashim ,Hind Hassan ,Ahmad Sazali Hamzah ²,Volkmar Vill ³,Mathias Wulf ³
Chemistry Department, University of Malaya, 50603, Kuala Lumpur Chemistry Department, University of Malaya, 50603 Kuala Lumpur ²University of Technology Mara, 40450 Shah Alam, Malaysia ³University of Hamburg, Institute of Organic Chemistry, D-20146 Hamburg, Germany
Although glycolipids exist in nature, they can also be synthesized either chemically or enzymatically. Due to their role in the nervous system and biomembranes, natural glycolipids are extensively studied by researchers, especially biochemists, but their liquid crystal state is not well understood. In this paper, starting from glucose and a series of branched-chain alcohols, novel alkyl glycosides have been synthesized. These compounds have been structurally elucidated using standard spectroscopic techniques like hydrogen (1H) NMR, carbon-13 (13C) NMR, and infra-red- (IR) and also using high resolution mass spectrometry (HRMS). Their thermotropic liquid crystalline properties were investigated using polarizing microscopy and differential scanning calorimetry. It was found that the shorter carbon chain analogues gave the smectic A phase while the longer ones gave only the columnar phase. The results were compared with those of the straight chain counterparts.

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