389799-72-8

Upstream product

• 109-97-7 pyrrole 
• 128376-64-7 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde 
• 87199-17-5 4-formylphenylboronic acid, 
• 76-09-5 2,3-dimethyl-2,3-butane diol 

Downstream Products

• 290356-48-8 5,15-bis(4-dioxylborylphenyl)porphyrin 

Relevant academic research and scientific papers

Methods and intermediates for the synthesis of dipyrrin-substituted porphyrinic macrocycles

The present invention provides dipyrrin substituted porphyrinic macrocycles, intermediates useful for making the same, and methods of making the same. Such compounds may be used for purposes including the making of molecular memory devices, solar cells and light harvesting arrays.

Investigation of two rational routes for preparing p-phenylene-linked porphyrin trimers

Multiporphyrin arrays with p-phenylene linkers, aryl groups at the non-linking meso positions, and no β-substituents are attractive constructs for light-harvesting applications. Condensation of a free base porphyrin-benzaldehyde and 5-mesityldipyrromethane (10 mM each) in CH2Cl2 containing 100 mM TFA at room temperature for 30-40 min followed by oxidation with DDQ afforded a p-phenylene-linked porphyrin trimer in 36% yield. Suzuki coupling of an iodo-porphyrin and a bis(dioxaborolane)-porphyrin (20 and 10 mM, respectively) in toluene/DMF (2:1) containing K2CO3 (8 equiv.) at 90-95°C for ～20 h afforded the same trimer in 66% yield. The former route was used to prepare a diethynyl substituted p-phenylene-linked porphyrin trimer. While the two routes are somewhat complementary in scope, both are convergent and proceed in a rational manner.