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2 article(s) from Senge, Mathias O

Structural effects of meso-halogenation on porphyrins

Keith J. Flanagan,
Maximilian Paradiz Dominguez,
Zoi Melissari,
Hans-Georg Eckhardt,
René M. Williams,
Dáire Gibbons,
Caroline Prior,
Gemma M. Locke,
Alina Meindl,
Aoife A. Ryan and
Mathias O. Senge

Beilstein J. Org. Chem. 2021, 17, 1149–1170, doi:10.3762/bjoc.17.88

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Graphical Abstract

Figure 1: 5-Halo-substituted porphyrins.

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Figure 2: Expanded view (thermal ellipsoid) of compound 1 in the crystal showing (A) stacking, (B) tilted edg...

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Figure 3: Expanded view (ball and stick) of compound 2 in the crystal showing (A) stacking, (B) bromine atoms...

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Figure 4: Expanded view (ball and stick) of compound 3 in the crystal showing (A) stacking and (B) edge-on in...

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Figure 5: Hirshfeld surfaces of compounds 1–3.

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Figure 6: Contact percentages of compounds 1–3.

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Figure 7: NSD charts for compounds 1–3.

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Figure 8: Expanded view (thermal ellipsoid plot) of compound 2A showing (A) the edge-on and stacking interact...

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Figure 9: 5-Halo-15-phenyl-substituted porphyrins.

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Figure 10: Expanded view (thermal ellipsoid plot) of compound 4 showing (A) tilted alignment of porphyrin ring...

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Figure 11: Expanded view (thermal ellipsoid plot) of compound 5 showing (A) porphyrin stacking and (B) Br···H ...

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Figure 12: Expanded view (thermal ellipsoid plot) of compounds 6 (A and C) and 7 (B and D) showing (A) Br···H ...

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Figure 13: 5,15-Di-halo-substituted porphyrins.

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Figure 14: Expanded view (thermal ellipsoid plot) of compound 9 showing the Br···H interactions with (A) pyrro...

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Figure 15: Expanded view (thermal ellipsoid plot) of compound 10 showing the (A) Br···H interactions with toly...

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Figure 16: Expanded view (thermal ellipsoid plot) of compound 11 showing the (A) edge-on interactions, (B) edg...

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Figure 17: Expanded view (thermal ellipsoid plot) of compound 13 showing (A) Br···H interactions with pyrrole ...

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Figure 18: Expanded view (ball and stick) of compound 13A showing (A) Br···H interactions with pyrrole units a...

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Figure 19: 5,10-Di-halo-substituted porphyrins.

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Figure 20: Expanded view (ball and stick) of compound 16 showing (A) stacking, (B) head-to-tail alignment, (C)...

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Figure 21: Honorable mentions of halogen-substituted porphyrins taken from the CSD database.

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Figure 22: Series 1 – 5,15-di-halo-substituted porphyrins.

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Figure 23: Series 2 – increasing number of halogen substituents.

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Figure 24: Series 3 – 5,10-di-halo-substituted porphyrins.

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Published 14 May 2021

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Towards triptycene functionalization and triptycene-linked porphyrin arrays

Gemma M. Locke,
Keith J. Flanagan and
Mathias O. Senge

Beilstein J. Org. Chem. 2020, 16, 763–777, doi:10.3762/bjoc.16.70

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Graphical Abstract

Figure 1: Triptycene as a scaffold and selected porphyrin and BODIPY arrays.

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Scheme 1: Sonogashira cross-coupling reactions to form symmetric porphyrin and BODIPY triptycene-linked dyads....

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Scheme 2: Sonogashira cross-coupling reactions to form a triptycene-substituted porphyrin monomer and an unsy...

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Scheme 3: Synthesis of the triptycene-porphyrin-triptycene complex 18.

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Figure 2: Single crystal X-ray structure of triptycene 5. (a) Molecular structure of 5 in the crystal with hy...

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Figure 3: Single crystal X-ray structure of triptycene-linked zinc-nickel porphyrin dimer 16 showing the conf...

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Figure 4: Views of the single crystal X-ray structure of triptycene-linked zinc-nickel porphyrin dimer 16 sho...

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Figure 5: Expanded structure view of the triptycene-linked zinc-nickel porphyrin dimer 16 showing the repeati...

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Figure 6: UV–vis of symmetric and unsymmetric triptycene porphyrin dimers 9 and 16, and the triptycene porphy...

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Figure 7: Emission spectrum of symmetric and unsymmetric triptycene-linked porphyrin dimers 9 and 16, and a t...

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Figure 8: Compounds used for spectroscopic comparisons.

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Figure 9: UV–vis spectra of various porphyrin/BODIPY dimers with different linker groups in CHCl₃.

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Figure 10: Fluorescence emission spectrum of various porphyrin/BODIPY dimers with different linker groups in C...

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Published 17 Apr 2020

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