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. 2024 Oct 24;9(Pt 10):x241028.
doi: 10.1107/S2414314624010289. eCollection 2024 Oct.

meso-5,15-Bis[3-(iso-propyl-idenegalacto-pyran-oxy)phen-yl]-10,20-bis-(4-methyl-phen-yl)porphyrin

Mickey Vinodh  1 , Fatemeh H Alipour  1 , Talal F Al-Azemi  1
Affiliations

meso-5,15-Bis[3-(iso-propyl-idenegalacto-pyran-oxy)phen-yl]-10,20-bis-(4-methyl-phen-yl)porphyrin

Mickey Vinodh et al. IUCrdata. .

Abstract

The crystal structure of a glycosyl-ated porphyrin (P_Gal2) system, C70H70N4O12, where two iso-propyl-idene protected galactose moieties are attached to the meso position of a substituted tetra-aryl porphyrin is reported. This structure reveals that the parent porphyrin is planar, with the galactose moieties positioned above and below the porphyrin macrocycle. This orientation likely prevents porphyrin-porphyrin H-type aggregation, potentially enhancing its efficiency as a photosensitizer in photodynamic therapy. Notable non-bonding C-H⋯O and C-H⋯π inter-actions among adjacent P_Gal2 systems are observed in this crystal network. Additionally, the tolyl groups of each porphyrin can engage in π-π inter-actions with the delocalized π-systems of neighboring porphyrins.

Keywords: crystal structure; glycosyl­ated porphyrin; photosensitizers.

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Figures

Figure 1
Figure 1
Crystal structure (displacement ellipsoid representation; 30% probability) of P_Gal2. Hydrogen atoms are omitted for clarity.
Figure 2
Figure 2
Crystal structure (ball-and-stick representation) of P_Gal2 showing exact orientations of toluyl and galacto­pyran­ose moieties with respect to the porphyrin plane.
Figure 3
Figure 3
Inter­molecular inter­actions experienced by a given P_Gal2 system with its neighboring counterparts; Symmetry codes: (i) 1 − x, −formula image + y, −z; (ii) 1 − x, formula image + y, −z; (iii) x, 1 + y, z; (iv) x, −1 + y, z; (v) 3 − x, −formula image + y, 1 − z; (vi) 3 − x, formula image + y, 1 - z.
Figure 4
Figure 4
Inter­molecular π–π inter­actions between neighbouring porphyrin units in the P_Gal2 crystal.
Figure 5
Figure 5
Packing pattern of P_Gal2 systems in the crystal network.
See this image and copyright information in PMC

References

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