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

Full Research Paper
Published 14 May 2021

PDF
Album
1. Graphical Abstract
2. Figure 1: 5-Halo-substituted porphyrins.
  
  Jump to Figure 1
3. Figure 2: Expanded view (thermal ellipsoid) of compound 1 in the crystal showing (A) stacking, (B) tilted edg...
  
  Jump to Figure 2
4. Figure 3: Expanded view (ball and stick) of compound 2 in the crystal showing (A) stacking, (B) bromine atoms...
  
  Jump to Figure 3
5. Figure 4: Expanded view (ball and stick) of compound 3 in the crystal showing (A) stacking and (B) edge-on in...
  
  Jump to Figure 4
6. Figure 5: Hirshfeld surfaces of compounds 1–3.
  
  Jump to Figure 5
7. Figure 6: Contact percentages of compounds 1–3.
  
  Jump to Figure 6
8. Figure 7: NSD charts for compounds 1–3.
  
  Jump to Figure 7
9. Figure 8: Expanded view (thermal ellipsoid plot) of compound 2A showing (A) the edge-on and stacking interact...
  
  Jump to Figure 8
10. Figure 9: 5-Halo-15-phenyl-substituted porphyrins.
  
  Jump to Figure 9
11. Figure 10: Expanded view (thermal ellipsoid plot) of compound 4 showing (A) tilted alignment of porphyrin ring...
  
  Jump to Figure 10
12. Figure 11: Expanded view (thermal ellipsoid plot) of compound 5 showing (A) porphyrin stacking and (B) Br···H ...
  
  Jump to Figure 11
13. Figure 12: Expanded view (thermal ellipsoid plot) of compounds 6 (A and C) and 7 (B and D) showing (A) Br···H ...
  
  Jump to Figure 12
14. Figure 13: 5,15-Di-halo-substituted porphyrins.
  
  Jump to Figure 13
15. Figure 14: Expanded view (thermal ellipsoid plot) of compound 9 showing the Br···H interactions with (A) pyrro...
  
  Jump to Figure 14
16. Figure 15: Expanded view (thermal ellipsoid plot) of compound 10 showing the (A) Br···H interactions with toly...
  
  Jump to Figure 15
17. Figure 16: Expanded view (thermal ellipsoid plot) of compound 11 showing the (A) edge-on interactions, (B) edg...
  
  Jump to Figure 16
18. Figure 17: Expanded view (thermal ellipsoid plot) of compound 13 showing (A) Br···H interactions with pyrrole ...
  
  Jump to Figure 17
19. Figure 18: Expanded view (ball and stick) of compound 13A showing (A) Br···H interactions with pyrrole units a...
  
  Jump to Figure 18
20. Figure 19: 5,10-Di-halo-substituted porphyrins.
  
  Jump to Figure 19
21. Figure 20: Expanded view (ball and stick) of compound 16 showing (A) stacking, (B) head-to-tail alignment, (C)...
  
  Jump to Figure 20
22. Figure 21: Honorable mentions of halogen-substituted porphyrins taken from the CSD database.
  
  Jump to Figure 21
23. Figure 22: Series 1 – 5,15-di-halo-substituted porphyrins.
  
  Jump to Figure 22
24. Figure 23: Series 2 – increasing number of halogen substituents.
  
  Jump to Figure 23
25. Figure 24: Series 3 – 5,10-di-halo-substituted porphyrins.
  
  Jump to Figure 24
Supp. Info