W&M ScholarWorks Undergraduate Honors Theses Theses, Dissertations, & Master Projects 5-2015 Synthesis and Characterization of pH-Sensitive Rhodamine 6G Spirolactam Structures Grace H. Taumoefolau Follow this and additional works at: https://scholarworks.wm.edu/honorstheses Part of the Organic Chemistry Commons, and the Other Chemistry Commons Recommended Citation Taumoefolau, Grace H., "Synthesis and Characterization of pH-Sensitive Rhodamine 6G Spirolactam Structures" (2015). Undergraduate Honors Theses. Paper 220. https://scholarworks.wm.edu/honorstheses/220 This Honors Thesis is brought to you for free and open access by the Theses, Dissertations, & Master Projects at W&M ScholarWorks. It has been accepted for inclusion in Undergraduate Honors Theses by an authorized administrator of W&M ScholarWorks. For more information, please contact
[email protected]. Table of Contents Page Table of Contents ii List of Figures and Tables iii Abstract 5 Acknowledgements 6 Introduction 8 Results and Discussion Chapter I: Optimization of R6G derivatives Reaction Conditions 14 Chapter II: Characterization of di-ortho R6G Derivatives 30 Chapter III: Attempt at achieving RB and R6G FRET 44 Experimental 57 References 66 Appendix 68 List of Figures and Tables Page Figure 1 Jablonski Diagram of Fluorescence 9 Figure 2 Fluorescence Excitation (Absorption) and Emission Spectra 9 Figure 3 Rhodamine B and Rhodamine 6G 10 Figure 4 Yuan’s RSL compounds ethanol and adamantyl substituted R6G 11 Figure 5 Rhodamine 6G with the functional group at the upper ring system altered from an ethyl acetate to a carboxylic acid (shorthand, R6G-acid) 15 Figure 6 R6G-Acid salt, with the quaternary ammonium cation at the xanthene core 17 Figure 7 Aromatic region in the NMR of R6G-dMA before the alumina column 26 Figure 8 Aromatic region in the NMR of R6G-dMA byproduct 26 Figure 9 An example of an oxidized amine due to alumina 27 Figure 10 NMR spectra of R6G-aniline.