2-Formyl-meso-tetraphenylporphine
Molecular Formula: C45H30N4O
CAS#: None
SMILES: O=CC1=C(N2)/C(C3=CC=CC=C3)=C4N=C(C=C\4)/C(C5=CC=CC=C5)=C(N/6)/C=CC6=C(C7=CC=CC=C7)\C8=N/C(C=C8)=C(C9=CC=CC=C9)\C2=C1
MDL#: None
Catalog#: F36177
Molecular weight: 642.759 g/mol
Appearance: Purple solid
Purity: >95%
Storage: Room temperature
Solubility: Organic solvents
Other names:
- 2-Formyl-5,10,15,20-tetraphenylporphyrin
- 2-Formyltetraphenylporphyrin
- 5,10,15,20-Tetraphenylporphyrin-2-carbaldehyde
- β-Formyl-meso-tetraphenylporphyrin
- β-Formyl-TPP
- TPP-CHO
- β-H₂TPPCHO
Fields of Interest
organic synthesis, porphyrin functionalization, β-functionalized porphyrins, photosensitizers, photochemistry, photocatalysis, supramolecular chemistry, chemical sensing, functional materials, heterocyclic chemistry, photodynamic research
Background & Applications:
2-Formyl-meso-tetraphenylporphine is a β-functionalized free-base tetraphenylporphyrin containing an aldehyde group directly attached to a pyrrolic position of the porphyrin macrocycle. Unlike formyl groups attached to a peripheral phenyl ring, the β-formyl substituent is electronically coupled to the conjugated porphyrin system, making this compound a useful intermediate for modifying the electronic and structural properties of tetraphenylporphyrins.
The reactive aldehyde group makes 2-formyl-5,10,15,20-tetraphenylporphyrin (TPP-CHO) a versatile porphyrin building block. It has been used in condensation, cycloaddition, reductive amination, and related functionalization reactions to prepare β-substituted porphyrins, benzoporphyrins, porphyrin–heterocycle conjugates, and extended molecular architectures.
Derivatives prepared from this scaffold have been investigated for chemical sensing, photocatalysis, photodynamic applications, singlet-oxygen generation, antimicrobial photosensitization, and functional molecular materials. The formyl group also provides a convenient synthetic handle for introducing pyridyl, amino, alkene, and other functional groups while retaining the characteristic optical properties of the porphyrin macrocycle.
Literature:
- Molecules 2017, 22(8), 1269; https://doi.org/10.3390/molecules22081269
- Journal of the American Chemical Society, 1986, vol. 108, # 13, p. 3608 – 3613, 10.1021/ja00273a010
- Tetrahedron, 2008, vol. 64, # 50, p. 11404 – 11408, 10.1016/j.tet.2008.09.088
- Moura, N. M. M.; Faustino, M. A. F.; Neves, M. G. P. M. S.; et al. “A New Synthetic Approach to Benzoporphyrins and Kröhnke Type Porphyrin-2-ylpyridines.” Chemical Communications 2012, 48, 6142–6144. DOI: 10.1039/C2CC30727H.
- This study uses 2-formyl-5,10,15,20-tetraphenylporphyrin directly as a starting material for the synthesis of benzoporphyrins and porphyrin-2-ylpyridine derivatives. The work demonstrates the value of the β-formyl group as a synthetic handle for constructing more complex porphyrin architectures and heterocycle-functionalized porphyrins.
- Ladeira, B. M. F.; Dias, C. J.; Gomes, A. T. P. C.; et al. “Cationic Pyrrolidine/Pyrroline-Substituted Porphyrins as Efficient Photosensitizers against E. coli.” Molecules 2021, 26, 464. DOI: 10.3390/molecules26020464.
- The researchers used 2-formyl-5,10,15,20-tetraphenylporphyrin as the precursor for porphyrin–pyrrolidine and porphyrin–pyrroline conjugates through 1,3-dipolar cycloaddition chemistry. Cationic derivatives generated singlet oxygen under visible light and showed photobactericidal activity against E. coli, illustrating the usefulness of TPP-CHO for developing photoactive porphyrin derivatives.
- Torres, P.; Guillén, M.; Escribà, M.; Crusats, J.; Moyano, A. “Synthesis of New Amino-Functionalized Porphyrins: Preliminary Study of Their Organophotocatalytic Activity.” Molecules 2023, 28, 1997. DOI: 10.3390/molecules28041997.
- This work employs 2-formyl-tetraphenylporphyrin as a starting scaffold for β-amino-functionalized porphyrins. The resulting porphyrin–amine hybrids were investigated as bifunctional organophotocatalysts, demonstrating how the aldehyde functionality can be used to introduce catalytic groups directly onto the porphyrin framework.