Abstract

The work presented herein focuses on the synthesis and characterization of polycyclic aromatic compounds for a wide variety of toxicological, analytical, and electronic applications. First, the modular synthesis of 12 dibenzo- and naphtho- fluoranthene polycyclic aromatic hydrocarbons (PAHs) via a Pd-catalyzed five-membered ring closing procedure is discussed. By understanding the various modes through which the Pd migrates during transformation, structural rearrangements were bypassed, obtaining regioselectivity through various redesigns in the synthetic route. Each compound in the serious was rigorously characterized via 1D/2D NMR, absorption and emission spectroscopy as well as cyclic voltammetry, which shows vast differences due to small structural changes between these constitutional isomers. Next, a series of polyphenylated organic ligands for zirconium metal organic frameworks is presented as materials for post-synthetic Scholl cyclodehydrogenation. Lastly, a series of organic linkers featuring covalently anchored redox-active pendants is explored for tuneable redox activity in Zr-based metal-organic frameworks. Thin-films were grown onto fluorine-doped tin-oxide glass electrodes and analyzed by cyclic voltammetry. This is the first reported pre-synthetic incorporation of covalently-bound ferrocenyl pendants into such a system. By attenuating the proportions of redox active and inactive links the oxidative peak currents could be tuned. This body of work represents a contribution toward the practical design and synthesis of polycyclic aromatic for a wide variety of analytical and electrochemical applications.

Notes

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Graduation Date

2019

Semester

Spring

Advisor

Uribe Romo, Fernando

Degree

Doctor of Philosophy (Ph.D.)

College

College of Sciences

Department

Chemistry

Degree Program

Chemistry

Format

application/pdf

Identifier

CFE0007512

URL

http://purl.fcla.edu/fcla/etd/CFE0007512

Language

English

Release Date

May 2020

Length of Campus-only Access

1 year

Access Status

Doctoral Dissertation (Campus-only Access)

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