Identifier

etd-04072017-160920

Degree

Doctor of Philosophy (PhD)

Department

Chemistry

Document Type

Dissertation

Abstract

4,4-Difluoro-4-bora-3a,4a-diaza-5-indacene (BODIPY) have drawn a large number of research attention, for its numerous useful application in the fields of material and biology. Small modification of this well-known fluophore has been shown to optimize its photophysical and chemical properties. This work mainly focuses on functionalization of BODIPY cores with halogenated atoms, particularly iodine, and their subsequent post-functionalization reactions, mainly cross-coupling reaction and substitutions, for various further applications. Chapter 1 of this dissertation gives a general overview of BODIPYs including their synthetic strategies, post-functionalization, and how BODIPYs are utilized in many biological applications. Chapter 2 mainly focuses on the synthesis and characterization of 3,5-diiodo-BODIPYs’ and 2,3,5,6-tetraiodo-BODIPY’s cross coupling products, together with the best coupling reaction methodology developments. Chapter 3 presents various aromatic substitution reactions of 3,5-diiodo-BODIPYs and 2,3,5,6-tetraiodo-BODIPY. The methods are developed with the best solvents, temperature and equivalents of nucleophiles. Due to the high reactivity of the 3,5-iodines, 123I radio labeling reactions were also attempted to produce 123I exchanged BODIPYs within one hour. Chapter 4 investigates the aromatization reactions on â,â’-bicyclo-BODIPYs, and a full scan of all 3,5-substited groups shows that only electron withdrawing groups are stable during the aromatization reactions. Based on this conclusion, a bis(isothiocyanate)-BODIPY that emits in the near-IR region was prepared and conjugated to an EGFR-L1 peptide. Chapter 5 reports the synthesis of nitrophenyl BODIPYs, and their electrochemical properties were studied, in collaboration with Dr. Karl Kadish group from University of Houston. In the reductive area, reversible peaks are found, which are corresponded to the reductive reactions on the nitrophenyl units.

Date

2017

Document Availability at the Time of Submission

Secure the entire work for patent and/or proprietary purposes for a period of one year. Student has submitted appropriate documentation which states: During this period the copyright owner also agrees not to exercise her/his ownership rights, including public use in works, without prior authorization from LSU. At the end of the one year period, either we or LSU may request an automatic extension for one additional year. At the end of the one year secure period (or its extension, if such is requested), the work will be released for access worldwide.

Committee Chair

Vicente,Graca

DOI

10.31390/gradschool_dissertations.4439

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