The innovation engine for new materials

Natalie Banakis


University of California, Santa Barbara


Chemical Engineering

Site Abroad: 

Eindhoven University of Technology, Netherlands


René Lafleur
Matt Baker

Faculty Sponsor(s): 

E.W. (Bert) Meijer

Faculty Sponsor's Department: 

Chemical Engineering

Project Title: 

The Synthesis and Clustering Kinetics of 1,3,5-Benzene-Tricarboxamides

Project Description: 

Recently, the behavior of water-soluble 1,3,5-benzene-tricarboxamides have been studied in great detail. In this study, the synthesis and clustering kinetics of water-soluble 1,3,5-benzene-tricarboxamide (BTA) derivatives were performed and analyzed. The BTA was decorated with an aliphatic spacer of either eleven or twelve carbons in length, a hydrophilic tail, which for this study was polyethylene glycol in order to increase its water solubility, and certain derivatives are dye labelled. The BTA can form fibers in water due to hydrogen bonding combined with hydrophobic effects. The clustering kinetics of these fibers were monitored by the Förster resonance energy transfer (FRET) between the Cyanine 5 and Cyanine 3 dye labelled BTA derivatives. The closer in proximity these dye labelled BTAs are, the higher the FRET. The FRET of these aggregates can be increased by the addition of single stranded DNA due to electrostatic forces between the ssDNA and the charged dye labelled BTA. Studying the clustering kinetics of the BTA allows us to determine the conditions for super selective monomer exchange. Using the same BTA derivative, different DNA lengths were compared to determine if super selective clustering behavior could be observed.


The purpose of synthesizing a different BTA derivative was to give the water-soluble BTA group a new direction of research. The synthesis of the BTA molecule with a twelve carbon hydrophobic spacer and azide functional group was done on a large scale. The next step was to attach an azide to a model compound. By proving the azide could be selectively and easily attached to the model compound, the opportunity to functionalize the glucose BTA derivative was opened. The glucose BTA was synthesized by attaching protected 2-propynyl-β-D-glucopyranoside to the azide functionalized BTA using a copper catalyzed azide-alkyne Huisgen cycloaddition, then de-protecting the sugar. The primary hydroxyl group of the glucose is then to be functionalized with an azide in order to employ the Huisgen cycloaddition again to attach the commercial Cyanine 3 and Cyanine 5 dyes.