Pd and Pt Complexes of Benzo-Fused Dipyrrins: Synthesis, Structure, Electrochemical, and Optical Properties

Snyder, Graden; Abuhadba, Sara; Lin, Neo; Lee, Wei-Tsung; Mani, Tomoyasu; Esipova, Tatiana V.

doi:10.1021/acs.inorgchem.4c00055

Inorg. Chem.

2024

DOI: 10.1021/acs.inorgchem.4c00055

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Pd and Pt Complexes of Benzo-Fused Dipyrrins: Synthesis, Structure, Electrochemical, and Optical Properties

Graden Snyder,

Sara Abuhadba,

Neo Lin

et al.

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Adjustable Regioselectivity for the Diels–Alder Reactions of Sulfolenodipyrrins upon Molecular Engineering on H-Bonds

Liu,

Zhang,

Fan

et al. 2024

J. Org. Chem.

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The Diels−Alder reactions of sulfolenodipyrrins prove to be an efficient way to construct aromatic ring-fused dipyrrins. However, adjustable annulation is still hard to achieve. To address this, molecular engineering on the H-bond has been employed. The α-position aryl group-modified sulfolenodipyrrins have been synthesized to react with various dienophiles in Diels− Alder reactions, affording the monoannulation products with different regioselectivity in good yields (45−76%). The remaining sulfolenopyrrole in monoadducts can undergo further fusion in the presence of dienophiles and TEMPO, giving the bisadducts with a lactam subunit in an appropriate yield. According to the crystal structures and theoretical calculations, the intramolecular H-bonds between the α-substituent and the nearby pyrrole confine the conjugation pathway of the dipyrrin core. With respect to the normal NH-sulfolenopyrrole, the imino-type one features low aromaticity, from which SO 2 extrusion generates more stable dipyrrin-diene, achieving regioselectivity. In addition, aromatic ring fusion results in red-shifted absorption and emission spectra, and the annulation units regulate the emission intensity. This work shows the versatility of intramolecular H-bonds in regulating the reaction through confinement of the conjugation system.

show abstract

Adjustable Regioselectivity for the Diels–Alder Reactions of Sulfolenodipyrrins upon Molecular Engineering on H-Bonds

Liu,

Zhang,

Fan

et al. 2024

J. Org. Chem.

View full text Add to dashboard Cite

show abstract

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Pd and Pt Complexes of Benzo-Fused Dipyrrins: Synthesis, Structure, Electrochemical, and Optical Properties

Cited by 1 publication

References 60 publications

Adjustable Regioselectivity for the Diels–Alder Reactions of Sulfolenodipyrrins upon Molecular Engineering on H-Bonds

Adjustable Regioselectivity for the Diels–Alder Reactions of Sulfolenodipyrrins upon Molecular Engineering on H-Bonds

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