A series of novel amphiphilic β-CD derivatives capable of forming hydrogen bonding networks of different strengths have been synthesized to probe the role of the hydrogen bonding network in the formation of self-assembled mesophases. Using differential scanning calorimetry (DSC), cross-polarized optical microscopy (POM) and X-ray diffractometry, two compounds were found to exhibit smectic mesophases. These correlated well with their abilities to form a hydrogen bonding network with sufficient strength to self-assemble. It was also observed that modifying the secondary face to interfere with the hydrogen bonding network significantly affects the Tc of a CD amphiphiles while the Tm temperature was not greatly affected.
