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Are Twisted Derivatives of PRODAN More Effective than Planar Derivatives as Detectors of Solvent Acidity in Micellar Solutions?

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Author: Nealy, Zachariah Bach
Advisor: Abelt, Christopher J.
Committee Members: Landino, Lisa M.; Tian, Jianjun Paul
Issued Date: 7/17/2012
Subjects: PRODAN
Excited hydrogen bonding
URI: http://hdl.handle.net/10288/16767
Description: Solvent acidity quanitifies the hydrogen bond donating ability of a solvent. One of the first measures of solvent acidity was ? 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.
Degree: Bachelors of Science in Chemistry

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