Self-assembly of amphiphilic calix[4]arenes with liquid crystalline properties

ORGN 737

Oana M. Martin, ommartin@students.wisc.edu, School of Pharmacy, University of Wisconsin-Madison, 777 Highland Ave., Madison, WI 53705 and Sandro Mecozzi, smecozzi@wisc.edu, School of Pharmacy and Department of Chemistry, University of Wisconsin, 777 Highland Ave, Madison, WI 53705.
New amphiphilic molecules based on the calix[4]arene scaffold were synthesized by appending perfluoroalkyl chains on the upper rim and polar groups on the lower rim of the macrocycle. The formation of a super-hydrophobic fluorous phase drives the self-assembly of these semi-fluorinated calix[4]arenes. Aggregates of different morphology, from vesicles and fibers to inverted micelles, were observed by transmission electron microscopy in various solvents. The structural characteristics of these molecules promote formation of mesophases with liquid crystalline-like properties. The phase behavior of the semi-fluorinated calix[4]arenes was analyzed by a combination of differential scanning calorimetry, thermal optical polarized microscopy and powder X-ray diffraction (XRD). Inspection of the XRD peaks suggests that the molecules can be arranged in a smectic phase with unstructured bilayers, such as smectic C.

 

Asymmetric Reactions, Molecular Recognition, Self Assembly, Bioorganic Chemistry, Process R&D
8:00 PM-10:00 PM, Wednesday, 16 March 2005 Convention Center -- Hall D, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, 14 March 2005 Convention Center -- Sails Pavilion, Sci-Mix

Division of Organic Chemistry

The 229th ACS National Meeting, in San Diego, CA, March 13-17, 2005