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4 article(s) from Senge, Mathias O

Unprecedented visible light-initiated topochemical [2 + 2] cycloaddition in a functionalized bimane dye

Metodej Dvoracek,
Brendan Twamley,
Mathias O. Senge and
Mikhail A. Filatov

Beilstein J. Org. Chem. 2025, 21, 500–509, doi:10.3762/bjoc.21.37

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Figure 1: Structures of a) the unfunctionalized bimane scaffold and b) the two isomers of bimanes with their ...

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Figure 2: a) Structures of the bimanes studied and b) the reaction scheme of the [2 + 2] photocycloaddition o...

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Figure 3: Synthetic approach to bimanes.

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Figure 4: View of the molecular structures in the crystal of the functionalized bimanes studied: a) Cl₂B (B),...

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Figure 5: View of the molecular structure in the crystal of a) symmetry generated by inversion bimanes Cl₂B (...

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Figure 6: View of the packing of the unit cells of a) Me₂B viewed normal to the c-axis and b) Me₄B viewed nor...

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Figure 7: UV–vis spectrum of Cl₂B after irradiation in DCM.

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Figure 8: Proposed mechanism for the topochemical [2 + 2] photocycloaddition of Cl₂B.

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Published 05 Mar 2025

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C–C Coupling in sterically demanding porphyrin environments

Liam Cribbin,
Brendan Twamley,
Nicolae Buga,
John E. O’ Brien,
Raphael Bühler,
Roland A. Fischer and
Mathias O. Senge

Beilstein J. Org. Chem. 2024, 20, 2784–2798, doi:10.3762/bjoc.20.234

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Figure 1: (A) Structures of tetrasubstituted 5,10,15,20-tetraphenylporphyrin (TPP, 1), dodecasubstituted 2,3,...

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Scheme 1: Reaction scheme for the synthesis of OET-xBrPPs and subsequent Ni(II) metalation.

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Figure 2: Substrates used for the investigations for the Suzuki–Miyaura coupling reactions.

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Scheme 2: Scope of arm-extended dodecasubstituted porphyrins synthesized via modification of the meso-para-ph...

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Scheme 3: Scope of arm-extended dodecasubstituted porphyrins synthesized via reaction at the meso-meta-phenyl...

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Scheme 4: Attempts of arm-extension of dodecasubstituted porphyrins at the meso-ortho-phenyl position.

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Scheme 5: Borylation and subsequent Suzuki–Miyaura coupling of porphyrin 13.

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Figure 3: View of the molecular structure of compounds 26 (top left) and 27 (top right) with atomic displacem...

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Figure 4: Left: packing diagram of 27 viewed normal to the c-axis showing the channels in the lattice with th...

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Figure 5: Left: view of part 0 2 in the molecular structure of the α₂β₂-atropisomer, 11 in the crystal, hydro...

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Figure 6: Schematic representation of porphyrin 37 showing a doubly intercalated structure.

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Published 04 Nov 2024

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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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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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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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