• 한국자기공명학회논문지
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• 제22권4호
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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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• 제22권8호
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• pp.932-934
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• 2001

• 한국진공학회지
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• 제17권5호
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• pp.375-380
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• 2008

Dipyrromethene 유도체 분자 중 하나인 삼각형 모양의 Co-DPM 거대분자 (Co-DPM-trimer, Fig. 1)를 이용하여 흑연 표면에서 다양한 저차원 분자 나노구조를 형성할 수 있었으며, 이를 주사 터널링 현미경(scanning tunneling microscope)으로 관찰하였다. Co-DPM-trimer 분자를 $CH_2Cl_2$ 용매에 녹여 흑연 표면에 뿌리면, 용매가 증발되며 그 동안 표면에 분자 나노구조가 형성된다. 본 연구에서는 다양한 두께의 긴 1차원 분자선과 2차원 구조인 육각형 패턴을 관찰하였다. 1차원 분자선과 2차원 육각형 패턴의 높낮이 및 구조를 분석한 결과, 1차원 분자선의 경우 흑연 표면에 'edge-on'정렬로 연속된 $\pi-\pi$ stacking 상호작용에 의해서, 그리고 육각형 패턴 구조는 'face-on'정렬을 통해서 형성된 것으로 보인다.

• Bulletin of the Korean Chemical Society
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• 제29권3호
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• pp.693-696
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• 2008

• Bulletin of the Korean Chemical Society
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• 제25권10호
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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.

• 공업화학
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• 제10권6호
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• pp.828-831
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• 1999

Meso-(mesityl)dipyrromethane(MS-DPM)과 4-nitrobenaldehyde로부터 5,15-bis(mesityl)-10,20-bis(4-amino)porphyrin[mesityl-$TPP(NH_2)$]을 합성하였다. Mesityl-$TPP(NH_2)$는 UV spectrophotometer[Soret-band(438 nm), Q-band(526, 572, 611 nm)]와 $^1H$-NMR spectroscopy에 의해 그 구조를 확인하였다. 3,3',4,4'-Benzophenone tetracarboxylic dianhydride(BTDA)와 2,2-bis(4-(4-aminophenoxy)-phenyl)hexafluoropropane(BAPHF)를 mesityl-$TPP(NH_2)$와 축합시켜 porphyrin 구조를 포함하는 copolyimide를 합성하였다. 제조된 copolyimide 역시 UV spectrophotometer [Soret-band (428 nm), Q-band (558 nm, 599 nm)]와 FT-IR spectrophotometer를 이용하여 그 구조를 확인하였고, 열분석 결과 $T_g$와 $T_m$은 각각 220.7와 $369.2^{\circ}C$였다.