194936-80-6

Upstream product

• 623-27-8 terephthalaldehyde, 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 15517-45-0 1,4-phenylenebis[(4-methoxypheny)lmethanone] 

Downstream Products

• 1186025-59-1 1,4-bis((p-methoxyphenyl)(2-pyrrolyl)methyl)benzene 

Relevant academic research and scientific papers

Synthesis of Nonaromatic and Aromatic Dithia Benzisapphyrins

A series of [24?€] dithia meta-benzisapphyrins and [22?€] dithia para-benzisapphyrins were synthesized by 3 + 2 condensation of appropriate benzitripyrrane with bithiophene diol under mild acid catalyzed conditions. The dithia m-benzisapphyrins and dithia p-benzisapphyrins were thoroughly characterized by HR-MS, 1D and 2D NMR, absorption, and electrochemical techniques. Our studies showed that dithia m-benzisapphyrins are nonaromatic, whereas the dithia p-benzisapphyrins are aromatic in nature. Thus, we demonstrated here that the dithiabenzisapphyrins can be made aromatic by replacing the m-phenylene moiety of the benzisapphyrin macrocycle with a p-phenylene unit. Furthermore, the studies also indicated that the aromaticity of the dithia p-benzisapphyrins was relatively more compared to the reported heterosapphyrins. The structural and spectral characteristics including aromaticity of the m-benzisapphyrins and p-benzisapphyrins were also discussed with the help of DFT, NICS, and TD-DFT studies.

Crowned Macrocycles Containing Two Pyrrolo[1,2-a] Indoles Created By Intramolecular Fusion

Heterocyclic fused-ring systems are of utmost importance because of their presence in many natural products with biological activity. Pyrroloindoles are tricyclic heterocycles that are present in various bioactive and medicinally valuable compounds. Herein, we report the synthesis of phenylene-bridged bis-pyrrolo[1,2-a]indole crowned macrocycles 1–3 in which the pyrrolo[1,2-a]indole moieties were formed via intramolecular fusion. The macrocycles were thoroughly characterized by 1D and 2D NMR, HRMS and X-ray crystallographic studies. The X-ray structure revealed that the two pyrrolo[1,2-a]indole moieties were parallel to each other, and one pyrrolo[1,2-a]indole unit was deviated by an angle of 9.54° while the other pyrrolo[1,2-a]indole unit was deviated by an angle of 12.0° from the mean plane defined by 28 core atoms. The macrocycles 1–3 absorb in the visible region and readily undergo oxidations because of their electron rich nature. The macrocycles 1–3 upon treatment with trifluoroacetic acid (TFA) generates the corresponding cation radicals 1–3.+ which were stable in the open air for a week. The cation radicals 1–3.+ absorb strongly in the NIR region and the experimental observations on crowned macrocycles 1–3 were corroborated by DFT and TD-DFT studies.

Steric control in the synthesis of p-benziporphyrins. formation of a doubly n-confused benzihexaphyrin macrocycle

The use of 1,4-phenylene-containing tripyrrane analogs provides a general route to expanded p-benziporphyrins. The course of macrocyclization shows a striking dependence on the steric bulk of meso substituents.