Synthesis Of Alkylthiol-containing Fluorene Derivatives For Gold Nanoparticle Functionalization

A novel synthetic methodology has been developed for attaching fluorene derivatives, containing different types of electron donating and accepting groups at the 2 and 7 positions, to gold nanoparticles of different sizes by exploiting the affinity of the thiol functional group for gold. The distance between the dye and nanoparticles was varied by introducing two alkyl chains containing different number of carbon atoms at the 9 position on the fluorene ring system. The methodology that was developed gave enough scope for performing Radiative Decay Engineering (RDE) studies, in order to investigate the impact of gold nanoparticles on the singlet oxygen quantum yields of fluorene dyes that already exhibit high singlet oxygen quantum yields as well as high two photon absorption (2PA) cross-sections. The dialkylation of the fluorene derivatives was accomplished by reacting the dye with [alpha], [omega]-dibromoalkanes containing different number of carbon atoms in a biphasic reaction mixture containing toluene and aqueous sodium hydroxide solution in the presence of tetrabutylammonium bromide (TBAB) as a phase transfer catalyst. The bromine atom on the alkyl chains was converted to thioester by reaction with potassium thioacetate. This was followed by the hydrolysis of the thioester to form the thiol moiety. The compounds synthesized were characterized using 1H and 13C nuclear magnetic resonance (NMR) spectroscopy and elemental analysis. Functionalization of gold nanoparticles was attempted by bringing into contact a solution of the thiol compound in toluene and an aqueous gold nanoparticles solution. UV-vis absorbance spectroscopy was used to monitor the progress of the attachment. Surface Enhanced Raman Scattering (SERS) spectroscopy was used to probe the enhancement of Raman signal by the metallic nanoparticles.

Author dc:creator

• Mukundarajan, Sriram

Contributors dc:contributor

• Belfield, Kevin

• fluorene
• gold nanoparticles
• functionalization
• radiative decay engineering.
• Chemistry

Language dc:language

English

Identifier

CFE0000769

OAI identifier oai:identifier

oai:stars.library.ucf.edu:etd-1597