Synthesis and Regioselective Functionalization of Tetrafluorobenzo-[α]-Fused BOPYPY Dyes

Authors

Sebastian O. Oloo, Louisiana State University
Guanyu Zhang, Louisiana State University
Petia Bobadova-Parvanova, Appalachian State University
Seleen Al Horani, Appalachian State University
Masa Al Horani, Appalachian State University
Frank R. Fronczek, Louisiana State University
Kevin M. Smith, Louisiana State University
Maria da Graça H. Vicente, Louisiana State University

Document Type

Article

Publication Date

5-20-2024

Abstract

The synthesis of a new bis-BF2 tetrafluorobenzo-[α]-fused BOPYPY dye from 4,5,6,7-tetrafluoroisoindole and 2-hydrazinopyrazine is reported. The regioselectivity of nucleophilic substitution reactions at the periphery of the tetrafluorinated BOPYPY and its α-bromo derivative were investigated using N-, O-, S-, and C-based nucleophiles. Among the aromatic fluorine atoms, the F² atom is consistently regioselectively substituted, except when the α-position contains a thiophenol group; in this case, F⁴ is substituted instead due to stabilizing π-π-stacking between the two aromatic groups. The α-bromo BOPYPY derivative also reacts under Stille cross-coupling reaction conditions to produce the corresponding α-substituted product. The spectroscopic properties of these new fluorinated BOPYPYs were investigated and compared with nonfluorinated analogs.

Publication Source (Journal or Book title)

Inorganic Chemistry

First Page

9164

Last Page

9174

Recommended Citation

Oloo, S., Zhang, G., Bobadova-Parvanova, P., Al Horani, S., Al Horani, M., Fronczek, F., Smith, K., & Vicente, M. (2024). Synthesis and Regioselective Functionalization of Tetrafluorobenzo-[α]-Fused BOPYPY Dyes. Inorganic Chemistry, 63 (20), 9164-9174. https://doi.org/10.1021/acs.inorgchem.4c00499