• Journal of the Korean Magnetic Resonance Society
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• v.22 no.4
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• pp.115-118
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• 2018

Dipyrromethane 2 functionalized with 3-chloropropyl group on the meso carbon undergoes an unusual intramolecular electrophilic aromatic substitution reaction in the presence of $NaN_3$ instead of a simple nucleophilic substitution reaction. As a result, a new chiral dipyrromethane 1 was synthesized. In this reaction, the ${\beta}$-carbon of the pyrrole ring functions as a nucleophile while the carbon next to the chlorine atom acts as an electrophile. Interestingly, this reaction progresses even in the absence of an acid catalyst. Compound 1 was fully characterized by $^1H-^1H$ and $^1H-^{13}C$ COSY NMR spectroscopic analyses and the high resolution EI mass spectrometry.

• Bulletin of the Korean Chemical Society
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• v.22 no.8
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• pp.932-934
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• 2001

• Journal of the Korean Vacuum Society
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• v.17 no.5
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• pp.375-380
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• 2008

We have investigated the low-dimensional nanostructures produced by adsorption of triangular Co coplexed dipyrromethane(DPM-trimer, Fig. 1) on graphite surface by using scanning tunneling microscope. DPM-trimer deposition on the graphite surface leads to the formation of long 1-D molecular wires and 2-D hexagonal patterns. We analyzed the heights and structures of 1-D molecular wires and 2-D hexagonal patterns. The 1-D molecular wires were formed 'edge-on' alignments on graphite surface result of continuos $\pi-\pi$ stacking interactions. The other case of 2-D hexagonal patterns were formed 'face-on' alignments on graphite surface.

• Bulletin of the Korean Chemical Society
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• v.29 no.3
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• pp.693-696
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• 2008

• Bulletin of the Korean Chemical Society
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• v.25 no.10
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• pp.1545-1550
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• 2004

meso-Functionalized dipyrromethanes 6-10 were synthesized by acid-catalyzed addition of pyrrole to ${\alpha}$-position of 2-alkenyl pyrroles. The regiochemistry of the reaction can be explained by either the formation of more stable carbocation intermediate or ${\beta}$-addition of ${\alpha},{\beta}$-unsaturated carbonyl compounds. The starting 2-alkenyl pyrroles were synthesized by Aldol condensation of 2-formylpyrrole with active methylene compounds such as nitromethane, diethylmalonate and malononitrile. Attempted ‘2+2' condensation of meso-diethylmalonyldipyrromethane, meso-(p-tolyl)dipyrromethane and p-tolualdehyde afforded three different porphyrins 12, 13 and 14 in reasonable yields. On the other hand, meso-(nitromethyl)dipyrromethane with p-(tbutyl) benzaldehyde resulted in the formation of three different porphyrins such as 5,15-dicyano-10,20-diarylporphyrin (16), 5-cyano-15-formyl-10,20-diarylporphyrin (17) and 5,15-diformyl-10,20-diarylporphyrin (18) in low yields. Conversion of nitromethyl groups to nitrile and (or) formyl group was observed under the porphyrin forming conditions.

• Applied Chemistry for Engineering
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• v.10 no.6
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• pp.828-831
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• 1999

5,15-Bis(mesityl)-10,20-bis(4-amino)porphyrin was synthesized with meso-(mesityl)dipyrromethane and 4-nitrobenzaldehyde. It was characterized with $^1H$-NMR spectroscopy, UV spectrophotometer, and GC-MASS. In UV spectrum, Soret-band(438 nm) and Q-bands(526, 572, 611 nm) were confirmed. In NMR spectrum, the characteristic peak of porphyrin was detected at -2.65 ppm. Copolyimide containing porphyrin structure was synthesized with mesityl-$TPP(NH_2)$, 3,3',4,4'-benzophenonetetracarboxylic dianhydride(BTDA) and 2,2-bis(4-(4-aminophenoxy)phenyl) hexafluoropropane(BAPHF) and characterized with UV and FT-IR spectrophotometer. The $T_g$ and $T_m$ of the synthesized copolyimide were 220.7 and $369.2^{\circ}C$, respectively.