Meso-Tetra (p-3-acetylthiopropoxyphenyl) Porphine
Molecular Formula: C64H62N4O8S4
CAS#: None
SMILES: CC(SCCCOC1=CC=C(/C2=C3C=CC(/C(C4=CC=C(OCCCSC(C)=O)C=C4)=C(N/5)/C=CC5=C(C6=CC=C(OCCCSC(C)=O)C=C6)\C7=N/C(C=C7)=C(C8=CC=C(OCCCSC(C)=O)C=C8)\C9=CC=C2N9)=N\3)C=C1)=O
MDL#: None
Catalog#: 41232
Molecular weight: 1143.48 g/mol
Appearance: Purple solid
Purity: >95%
Storage: -20 C
Solubility: Organic solvents
Other names:
- S,S’,S”,S”’-(((porphyrin-5,10,15,20–tetrayltetrakis (benzene-4,1-diyl)) tetrakis(oxy)) tetrakis(propane-3,1-diyl)) tetraethanethioate
Fields of Interest
surface functionalization, self assembled monolayers SAMS, nanosheets, porphyrin chemistry, nanomaterials, 2D materials, transition metal dichalcogenides (TMDCs), MoSe₂ functionalization, photocatalysis, electrocatalysis, hydrogen evolution, photoelectrochemistry, molecular electronics, surface chemistry
Background & Applications
meso-Tetra(p-3-acetylthiopropoxyphenyl) Porphine is a sulfur-functionalized free-base porphyrin containing four thioacetate-protected groups positioned around the porphyrin macrocycle. The acetylthio groups provide protected precursors to reactive thiol functionalities, enabling the porphyrin to be incorporated into surfaces, nanosheets, and organic–inorganic hybrid materials while retaining the characteristic optical and electronic properties of the porphyrin core.
This porphyrin scaffold is particularly useful in surface functionalization and advanced nanomaterials research. Thiolated derivatives have been used to covalently functionalize chemically exfoliated MoSe₂ nanosheets, producing porphyrin–MoSe₂ hybrid materials with modified electrocatalytic and photoelectrochemical behavior. Related sulfur-functionalized porphyrins can also bind to gold surfaces through strong sulfur–gold interactions. Potential applications include TMDC functionalization, photocatalysis, light-assisted hydrogen evolution, electrocatalysis, molecular sensing, photoactive interfaces, and porphyrin-based hybrid nanomaterials.
Literature:
- Blanco, M.; Lunardon, M.; Bortoli, M.; et al. “Tuning on and off chemical- and photo-activity of exfoliated MoSe₂ nanosheets through morphologically selective ‘soft’ covalent functionalization with porphyrins.” Journal of Materials Chemistry A 2020, 8, 11019–11030. DOI: 10.1039/D0TA03302B.
This study describes the covalent functionalization of exfoliated MoSe₂ nanosheets with thiol-functionalized porphyrins. The resulting porphyrin–MoSe₂ hybrid materials were evaluated for their photochemical and electrocatalytic properties, including light-assisted hydrogen evolution. - Suárez, S. A.; Fonticelli, M. H.; Rubert, A. A.; et al. “A Surface Effect Allows HNO/NO Discrimination by a Cobalt Porphyrin Bound to Gold.” Inorganic Chemistry 2010, 49, 6955–6966. DOI: 10.1021/ic1007022. This work investigates a cobalt porphyrin containing acetylthiopropoxy substituents for immobilization on gold surfaces. The sulfur-containing groups facilitate surface attachment, demonstrating the utility of this porphyrin framework in electrochemical interfaces, sensing, and surface-functionalized materials.