Semester of Graduation

Spring 2026

Degree

Master of Science (MS)

Department

Chemistry

Document Type

Thesis

Abstract

Abstract

This work explores the functionalization of 1,3,5,7-tetraphenyl-aza-BODIPY at the boron center with cyano, methoxy, methyl, n-butyl, isothiocyanate, and propargyloxy groups. The effects of these substitutions on the spectroscopic properties were evaluated in chloroform using UV-vis and fluorescence spectroscopy. The stability of these aza-BODIPY derivatives in trifluoroacetic acid (TFA) was further evaluated using 11B and 1H-NMR, UV-vis, fluorescence spectroscopy, mass spectrometry, and thin-layer chromatography. The results indicate that 2,6-dinitro-4,4’-difluoro-aza-BODIPY 2a and the 4,4’-dicyano-aza-BODIPY 3 are the most stable among this series, remaining unchanged over 3 days after the addition of excess TFA, while the 4,4’-dimethoxy-aza-BODIPY 5 is the least stable, decomposing within 1h after TFA addition. The 4,4’-difluoro-aza-BODIPY 2 was found to have intermediate stability, being stable for up to 2 days after TFA addition. All other compounds, 4,4’-dimethyl-aza-BODIPY 4, 4,4’-dipropargyloxy-aza-BODIPY 6, 4,4’-dibutyl-aza-BODIPY 7 and 4,4’-diisothiocyanato-aza-BODIPY 8 are less stable than 2, remaining stable up to 9h after addition of TFA.

Date

3-18-2026

Committee Chair

Vicente Graca

LSU Acknowledgement

1

LSU Accessibility Acknowledgment

1

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