Degree

Doctor of Philosophy (PhD)

Department

Chemistry

Document Type

Dissertation

Abstract

Chapter 1 of this dissertation briefly introduced the background and fundamental concept of boron dipyrrins (BODIPYs), their postfunctionalization strategy, and applications.

Chapter 2 is based on a previously published article in ACS Omega 2018, 3 (5), 5502–5510. In this chapter, the relative stability of a series of 4,4-disubstituted BODIPYs (−F, −CN, −Ph, −Me, −OMe) was investigated comprehensively through NMR, UV–vis, fluorescence, TLC, mass spectrometry, IR, and computational calculation. Our results show that the 4,4-dicyano-BODIPY is highly stable under strongly acidic conditions (trifluoroacetic acid).

Chapter 3 is based on a previously published article in Inorg. Chem. 2019, 58 (17), 11614-11621. This chapter described the synthesis of several cyclic BODIPY–Gly conjugates, with five different protecting groups on glycine. The experimental and computational data unambiguously proved the existence of up- and down-conformers. Besides, their aqueous stability and chemical stability in TFA were analyzed through spectroscopic study.

Chapter 4 reported a library of BODIPY-amino acid conjugates with different side chains on amino acids. Their photophysical and biological properties were systematically studied. The results show that the cytotoxicity of the BODIPY-amino acid conjugates depends on the special spiro ring structure and the intrinsic properties of the amino acids.

Chapter 5 is based on a previously published article in Eur. J. Org. Chem. 2020, 8, 971-977. In this chapter, several novel linker-free aza-BODIPY-glutamine conjugates were investigated experimentally and computationally. All the aza-BODIPY derivatives absorb and emit in the near-IR region, and the 2,6-dibromo-aza-BODIPY can be applied as photosensitizers for photodynamic therapy. The novel spiro structures of aza-BODIPYs show enhanced cytotoxicity in human carcinoma HEp2 cells, thus could be potentially used as cancer therapeutics.

Committee Chair

Vicente, Graca

Available for download on Sunday, August 13, 2028

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