Examining Committee  
Dr. Donald Mercer, Chair  
Dr. Michael Rogers, Advisor  
Dr. Maria Corradini, Advisory Committee Member   
Dr. Loong-Tak Lim, Department Member  
  
TITLE: MOLECULAR FEATURES OF 1,3:2,4 DIBENZYLIDENE-D-SORBITOL (DBS) THAT  DRIVE SELF-ASSEMBLY  

ABSTRACT:  
Dibenzylidene-D-sorbitol  (DBS)  is  the  most  well-known  molecule  among  the gelators because of its potential to produce a gel across a broad range of organic solvents. Chemical modification of DBS in this study shows how hydrogen bonding  on different carbon positions alters the Hansen space attributed to gelation and helps us in better understanding molecular driving forces governing molecular gels.  These newly synthesized molecules alter a single functional group, one at a time, to assess the forming hydrogen  bonding network while keeping maintaining the remaining structure of DBS. To assess the role of hydrogen bonding at the primary and  secondary  alcohols  of  DBS,  each  hydroxyl  group  was  acetylated  selectively.  Furthermore, selective deoxygenation of each hydroxyl group was performed to completely eliminate hydrogen bonding at either the primary or secondary alcohol  groups.