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

Mickey Vinodh; Fatemeh H Alipour; Talal F Al-Azemi

doi:10.1107/S2414314624010289

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

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

Authors

Mickey Vinodh¹, Fatemeh H Alipour¹, Talal F Al-Azemi¹

Affiliation

¹ Department of Chemistry, Kuwait University, PO Box 5969, Safat 13060, Kuwait.

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.

Grants and funding

The support of the Kuwait University (research grant No. SC 05/23) and the facilities of RSPU through grant Nos. GS 03/08 (Rigaku RAPID II, Japan), GS 01/01 (NMR-Bruker DPX Avance 400, Germany) and GS 01/03 (GC MS Thermo Scientific, Germany) are gratefully acknowledged.