Date Thesis Awarded

7-2012

Document Type

Honors Thesis

Degree Name

Bachelors of Science (BS)

Department

Chemistry

Advisor

Christopher J. Abelt

Committee Member

Lisa M. Landino

Committee Member

Jianjun Paul Tian

Abstract

Solvent acidity quanitifies the hydrogen bond donating ability of a solvent. One of the first measures of solvent acidity was α parameter developed by Kamlet-Taft. Later Catalan and colleagues developed the SA parameter. This study proposes that the emission intensity of several PRODAN derivatives can also be used as a measure of SA. The photophysical properties of PRODAN (1) (6-propionyl-2-(dimethylamino)naphthalene),3-(dimethylamino)-8,9,10,11-tetrahydro-7H-cyclohepta[a]naphthalene-7-one (2), 6-(2,2-dimethyl-propion-1-yl)-2-(dimethylamino) naphthalene (3), 2,2-dimethyl-1-(4-methyl-1,2,3,4-tetrahydrobenzo[f]quinolin-8-yl)propan-3-one (4) 7-(dimethylamino)-3,and 4-dihydrophanthren-1(2H)-one (5) are reported. These compounds are classified as planar derivatives (1 and 5), which are theorized to be worse at detecting solvent acidity, and twisted derivatives (2, 3, and 4), which are theorized to be better at detecting solvent acidity, based on their geometry. These compounds were used to create correlation curves between solvent acidity and log((E/A)max/(E/A)) values. In this experiment, E is the emission spectra maximum intensity or integrated emission value and A is the absorbance value at 365nm. This correlation curve was used to calculate the apparent solvent acidity that the PRODAN probes sense while in micellar (SDS, CTAB) and reverse micellar (TX-100) solutions. Compound 2 is the most suited as a probe of solvent acidity.

Creative Commons License

Creative Commons License
This work is licensed under a Creative Commons Attribution-Noncommercial-No Derivative Works 3.0 License.

Comments

Thesis is part of Honors ETD pilot project, 2008-2013. Migrated from Dspace in 2016.

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