5,15-(di-3,5-di-tert-butylphenyl)porphyrin

5,15-(di-3,5-di-tert-butylphenyl)porphyrin

Molecular Formula: C48H54N4

CAS#: 173613-63-3

SMILES: CC(C)(C)C1=CC(/C(C2=N/C(C=C2)=C\3)=C(C=C/4)/NC4=C/C(C=C/5)=NC5=C(C6=CC(C(C)(C)C)=CC(C(C)(C)C)=C6)/C7=CC=C3N7)=CC(C(C)(C)C)=C1

MDL#: MFCD30471365

Catalog#: D34106

Molecular weight: 686.97 g/mol

Appearance: Purple solid

Purity: >95%

Storage: room temperature

Solubility: organic solvents like dichloromethane, Chloroform, THF

Other names:

• 5,15-Bis[3,5-bis(1,1-dimethylethyl)phenyl]-21H,23H-porphine
• 5,15-Bis[3,5-di(tert -butyl)phenyl]porphyrin

Fields of Interest

porphyrin chemistry, organic synthesis, supramolecular chemistry, porphyrin arrays, light-harvesting materials, photophysics, molecular electronics, metal coordination chemistry, conjugated materials, photon upconversion, molecular spin systems, porphyrin tapes

Background & Applications

5,15-(Di-3,5-di-tert-butylphenyl)porphyrin is a free-base trans-diaryl porphyrin featuring two bulky 3,5-di-tert-butylphenyl substituents at opposite meso positions. The tert-butyl groups improve compatibility with organic solvents and provide steric bulk around the porphyrin framework, while the unsubstituted 10- and 20-meso positions offer useful sites for further chemical functionalization. Bulky alkyl-substituted diarylporphyrins are particularly useful when good solution handling and controlled intermolecular interactions are desirable.

This porphyrin is a versatile building block for functional porphyrins, metalloporphyrins, and extended porphyrin architectures. The free-base macrocycle can be metalated with metals such as Zn(II) or Ni(II), while its available meso positions can be modified to introduce additional aromatic, heterocyclic, or functional groups. Related derivatives have been investigated in supramolecular self-assembly, light harvesting, photon upconversion, directly linked porphyrin arrays, porphyrin tapes, conjugated molecular materials, and molecular spin systems.

Literature:

• J. Phys. Chem. A (2000) 104 (15): 3287–3298. https://doi.org/10.1021/jp9942623
• RSC Adv. (2020) 10 (12): 7048–7057 https://doi.org/10.1039/c9ra09711b
• Reis, M. J. A.; Vieira, C.; Bartolomeu, M.; et al. “A₂B₂-type porphyrins enhanced by N-donor units: Synthesis optimization and photodynamic efficiency towards S. aureus.” Bioorganic Chemistry 2025, 162, 108607. DOI: 10.1016/j.bioorg.2025.108607.
  • This study uses 5,15-bis(3,5-di-tert-butylphenyl)porphyrin directly as a starting material for the preparation of functional A₂B₂ porphyrins containing N-donor groups at the remaining meso positions. The work highlights the value of this porphyrin as a versatile synthetic scaffold for preparing substituted photoactive porphyrins.
• Ogawa, T.; Nishimoto, Y.; Ono, N.; Yoshida, N.; Osuka, A. “One-pot electrochemical formation of meso,meso-linked porphyrin arrays.” Chemical Communications 1998, 337–338. DOI: 10.1039/A707653C.
  • The Zn(II) complex of 5,15-bis(3,5-di-tert-butylphenyl)porphyrin was electrochemically oxidized to form directly meso,meso-linked porphyrin oligomers, including arrays containing up to eight porphyrin units. The study demonstrates the usefulness of this porphyrin framework in constructing extended conjugated porphyrin architectures.
• Balaban, T. S.; Goddard, R.; Linke-Schaetzel, M.; Lehn, J.-M. “2-Aminopyrimidine Directed Self-Assembly of Zinc Porphyrins Containing Bulky 3,5-Di-tert-butylphenyl Groups.” Journal of the American Chemical Society 2003, 125, 4233–4239. DOI: 10.1021/ja029548r.
  • Derivatives of the 5,15-bis(3,5-di-tert-butylphenyl)porphyrin scaffold bearing aminopyrimidine groups were prepared and studied as self-assembling Zn(II) porphyrins. Their concentration- and temperature-dependent aggregation demonstrates the potential of this structural platform for supramolecular porphyrin arrays and light-harvesting systems.