Observation of a Chiral Smectic Phase in Azobenzene-Linked Bolaamphiphiles Containing Free Sugars


  • The authors thank the Defense Research and Development Organization (GAP 102839) and the Council of Scientific and Industrial Research (CSIR), Government of India, for financial assistance. This is contribution No. 182 RRLT-PPD from RRL (CSIR), Trivandrum. Supporting Information is available online from Wiley InterScience or from the author.


Amphiphilic sugars exhibit both lyotropic and thermotropic liquid-crystalline behavior. Interestingly, in spite of the abundance of chiral centers in amphiphilic sugars, their liquid-crystalline phases do not exhibit macroscopic chirality. Herein, we report on the first observation of macroscopic chirality in sugar-based bolaamphiphiles containing free hydroxyl groups. The manifestation of the chiral smectic C* phase in these bolaamphiphiles has been observed to be critically dependent on the presence of the azobenzene moiety and the suitable length of the methylene spacer. These results imply that by suitable selection of linker groups, mesogenic bolaamphiphiles possessing macroscopic chirality can be designed using a variety of naturally available sugar derivatives.