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Investigating Color Additive Molecules for Pharmaceutical and Cosmetic Rowan University Rowan Digital Works Theses and Dissertations 6-17-2019 Investigating color additive molecules for pharmaceutical and cosmetic applications: A comparison of theoretical and experimental UV-visible absorbance spectra in tunable solvents Jacqueline Casey Mohen Rowan University Follow this and additional works at: https://rdw.rowan.edu/etd Part of the Medicinal-Pharmaceutical Chemistry Commons Recommended Citation Mohen, Jacqueline Casey, "Investigating color additive molecules for pharmaceutical and cosmetic applications: A comparison of theoretical and experimental UV-visible absorbance spectra in tunable solvents" (2019). Theses and Dissertations. 2690. https://rdw.rowan.edu/etd/2690 This Thesis is brought to you for free and open access by Rowan Digital Works. It has been accepted for inclusion in Theses and Dissertations by an authorized administrator of Rowan Digital Works. For more information, please contact [email protected]. INVESTIGATING COLOR ADDITIVE MOLECULES FOR PHARMACEUTICAL AND COSMETIC APPLICATIONS: A COMPARISON OF THEORETICAL AND EXPERIMENTAL UV-VISIBLE ABSORBANCE SPECTRA IN TUNABLE SOLVENTS by Jacqueline C. Mohen A Thesis Submitted to the Department of Chemistry & Biochemistry College of Science and Mathematics In partial fulfillment of the requirement For the degree of Master of Science in Pharmaceutical Sciences at Rowan University May 9, 2019 Thesis Chair: Timothy D. Vaden, Ph.D. © 2019 Jacqueline C. Mohen Dedications To Christine and Timothy, for having faith in me against all odds, and the divine patience to wait for a phenomenal outcome. iii iv Acknowledgment Special thanks to Nathalie Nicole Malinao, who went above and beyond to help me save this manuscript file from being compromised by an aggressive hacking attempt. v vi Abstract Jacqueline C. Mohen INVESTIGATING COLOR ADDITIVE MOLECULES FOR PHARMACEUTICAL AND COSMETIC APPLICATIONS: A COMPARISON OF THEORETICAL AND EXPERIMENTAL UV-VISIBLE ABSORBANCE SPECTRA IN TUNABLE SOLVENTS 2018-2019 Timothy D. Vaden Master of Science in Pharmaceutical Sciences Color additive molecules have widespread applications ranging from ingestible foods and pharmaceutics to non-ingestible cosmetics and other naturally or synthetically- developed consumer products available worldwide. Certification for approved use of color additives varies globally; therefore, a feasible method to analyze existing color additives or to design novel color additive molecules with enhanced or otherwise desired physicochemical properties (such as hue) is in high demand for universal adoption. The studies herein provide sufficient proof that density functional theory and time-dependent density functional theory serve as effective predictive modeling techniques for generating theoretical maximum absorbance spectral peak responsivity for a single color additive molecule structure in the virtual workspace, as well as for multiple (heterodimeric and heterotrimeric) structures represented simultaneously. Furthermore, DFT and TD-DFT can be used to analyze changes in hue attributed to structural anomalies in molecules due to tautomerism, vibronic effects, intra- or intermolecular interactions, implicit or explicit solvation effects, or charge transfer effects on the structure represented in a given solvent or in vapor phase. Advancements in computational processing make incorporation of these and similar advanced ab initio quantum chemical methods more tangible for the modern pharmaceutical or cosmetic formulator to use in perfecting batch hue. vii viii Table of Contents Abstract ............................................................................................................................vii List of Figures ..................................................................................................................xiii List of Tables ...................................................................................................................xxii Introduction ......................................................................................................................1 Chapter 1: Predicting Color Appearance of Pharmaceutical and Cosmetic Color Additive Mixtures in Ethanol using TD-DFT Calculations ............................................................44 Materials and Methods ...............................................................................................45 Experimental Data .....................................................................................................55 Theoretical Data .........................................................................................................57 Individual Color Additive Molecules: Experimental λmax comparison to theoretical TD-DFT simulation maximum absorbance spectral peak responsivity (λmax) under 3 simulation conditions ....................................................................73 Heterodimeric Mixtures: Experimental λmax comparison to theoretical TD-DFT simulation maximum absorbance spectral peak responsivity (λmax) under 3 simulation conditions ...........................................................................................76 Heterotrimeric Mixture: Experimental λmax comparison to theoretical TD-DFT simulation maximum absorbance spectral peak responsivity (λmax) under 3 simulation conditions ...........................................................................................79 Discussion ..................................................................................................................82 Individual Color Additives ..................................................................................82 D&C Blue No. 6 “Indigo” .............................................................................83 D&C Yellow No. 11 “SS Quinoline Yellow” ...............................................89 D&C Red No. 36 “American Vermillion” .....................................................95 Heterodimeric Mixtures .......................................................................................100 D&C Blue No. 6 and D&C Yellow No. 11 ...................................................100 ix D&C Yellow No. 11 and D&C Red No. 36 ..................................................103 D&C Blue No. 6 and D&C Red No. 36 .........................................................106 Heterotrimeric Mixture ........................................................................................108 D&C Blue No. 6, D&C Yellow No. 11, and D&C Red No. 36 ...................108 Conclusion .................................................................................................................111 Chapter 2: Solvent Effects on Interaction Energies of Alternating Color Additive Molecular Structures in Conventional and Ionic Liquid Solvents using TD-DFT ..........125 Materials and Methods ...............................................................................................129 Experimental Data .....................................................................................................134 Theoretical Data .........................................................................................................139 FD&C Red No. 40 “Allura Red” .........................................................................141 D&C Yellow No. 11 “SS Quinoline Yellow” .....................................................142 Brilliant Cresyl Blue ............................................................................................143 HOMO-LUMO Surface Maps .............................................................................144 Interaction Energies .............................................................................................154 Discussion ..................................................................................................................156 FD&C Red No. 40 “Allura Red” .........................................................................156 D&C Yellow No. 11 “SS Quinoline Yellow” .....................................................162 Brilliant Cresyl Blue ............................................................................................166 Static Dielectric Constant Comparison in [EMIM]OAc ......................................174 Conclusion .................................................................................................................177 Chapter 3: Brilliant Cresyl Blue in Tunable Ionic Liquid Solvents: A Comparison between Experimental and TD-DFT Spectra ...................................................................196 Materials and Methods ...............................................................................................201 x Experimental Data .....................................................................................................209 Theoretical Data .........................................................................................................211 Discussion ..................................................................................................................226 Brilliant Cresyl Blue in Water .............................................................................226 Brilliant Cresyl Blue in Ethanol ...........................................................................228 Brilliant Cresyl Blue in Ionic Liquids ..................................................................228 BCB in 1-butyl-3-methylimidazolium chloride ............................................229 BCB in 1-butyl-3-methylimidazolium
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