European Journal of Chemistry

Synthesis and properties of 3-ethynylthiophene containing BODIPY derivatives

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Published: Dec 31, 2017
DOI: https://doi.org/10.5155/eurjchem.8.4.321-327.1634
Keywords:
BODIPY, Thiophene, Stokes shift, Fluorescence, Singlet oxygen, Photodynamic therapy
Section
Research Article
Issue
Vol. 8 No. 4 (2017): December 2017
Dates
Received 2017-08-01
Accepted 2017-09-09
Published 2017-12-31


Main Article Content

Reuben Warshawsky
Department of Chemistry, University of Southern Indiana, Evansville, Indiana 47712, USA
Jason Vaal
Department of Chemistry, University of Southern Indiana, Evansville, Indiana 47712, USA
Priya Hewavitharanage
Department of Chemistry, University of Southern Indiana, Evansville, Indiana 47712, USA

Abstract

Green, red and far-red emitting Borondipyrromethene (BODIPY) derivatives with 3-ethynylthiophene units at various positions around the BODIPY core were synthesized and their photophysical properties were studied. 3-Ethynylthiophene substitution at the 2,6 positions caused significant increase in Stokes shift while substitution at the 8 and 4,4’ positions had no effect. Photooxidation of 1,3-diphenylisobenzofuran (DPBF) in the presence of 3-ethynylthiophene substituted BODIPY derivatives confirmed singlet oxygen generation. 3-Ethynylthiophene substitution at the 2,6 positions is more effective in singlet oxygen generation compared to 4’4 substitutions. Substitution through phenyl group at the meso (8) position gave the lowest rate for singlet oxygen production. All 3-ethynylthiophene containing BODIPY derivatives were highly photo-stable under our experimental conditions.


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Warshawsky, R.; Vaal, J.; Hewavitharanage, P. Synthesis and Properties of 3-Ethynylthiophene Containing BODIPY Derivatives. Eur. J. Chem. 2017, 8, 321-327.

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Supporting Agencies

The University of Southern Indiana Endeavor Award for Research & Creativity (Project no, 17786-01000) and by the Lilly Summer Student Research Fellowship (Project no, 25075-01820)
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