Date Thesis Awarded

5-2015

Access Type

Honors Thesis -- Access Restricted On-Campus Only

Degree Name

Bachelors of Science (BS)

Department

Chemistry

Advisor

Elizabeth J. Harbron

Committee Members

Robert J. Hinkle

Deborah C. Bebout

Gexin Yu

Abstract

As an extension of the RB sterics project, which studies the tunability of fluorescence turn-on pK_a as a function of substituent A-value, similar efforts with R6G are presented. In light of previous failed attempts at di-ortho R6G derivative synthesis, this study sought to optimize synthetic procedures as well as explore alternative synthetic pathways. Optimization efforts, summarized by maintaining a cold and anhydrous reaction environment, were ultimately fruitful, significantly raising the chances at isolating product although purification of these products still poses some questions. Relatively pure products were then characterized with fluorescence studies, NMR spectroscopy and computational methods. R6G derivatives generally fluoresced at higher pK_a as compared to their RB counterparts, albeit to a lesser extent than expected. Computation of R6G derivatives’ optimized geometries aided in understanding the NMR spectra of a few compounds. Methods for observing RB and R6G FRET were also explored, namely by investigating dye-embedded pHEMA films and attempting to covalently bind the two dyes together using azide-alkyne click chemistry.

Recommended Citation

Taumoefolau, Grace H., "Synthesis and Characterization of pH-Sensitive Rhodamine 6G Spirolactam Structures" (2015). Undergraduate Honors Theses. William & Mary. Paper 220.
https://scholarworks.wm.edu/honorstheses/220