抄録
Synthesis and properties of a novel meso-oxo carbaphlorin analogue embedded with an N-free pyrazole moiety are described. The N-benzyl precursor was prepared by a [3 + 1]-MacDonald condensation of N-benzyl pyrazole dialdehyde and β-alkyl-substituted tripyrrane dicarboxylic acid and subsequent oxidation by ferric chloride. Upon deprotection of the benzyl group, the resulting N-free oxophlorin analogue formed a unique supramolecular dimer through mutual hydrogen bonding interactions between the pyrazole NH and meso-carbonyl group. The assembled behaviour was characterised by various spectroscopies, X-ray crystallographic analysis and vapour pressure osmometry. Under the similar reaction conditions, the condensation of meso-phenyl-substituted tripyrrane derivative afforded an unprecedented tetrapyrrolic macrocycle fused with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone unit at their α-pyrrolic positions. The X-ray crystallographic analysis of the macrocycle revealed a twisted core structure, and nonaromatic nature was elucidated.
| 元の言語 | 英語 |
|---|---|
| ページ（範囲） | 8-16 |
| ページ数 | 9 |
| ジャーナル | Supramolecular Chemistry |
| 巻 | 29 |
| 発行部数 | 1 |
| DOI | |
| 出版物ステータス | 出版済み - 1 2 2017 |
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All Science Journal Classification (ASJC) codes
- Chemistry(all)
これを引用
Supramolecular dimeric structures of pyrazole-containing meso-oxo carbaphlorin analogues. / Ishida, Masatoshi; Fujimoto, Hiroyuki; Morimoto, Tatsuki; Mori, Shigeki; Toganoh, Motoki; Shimizu, Soji; Furuta, Hiroyuki.
：: Supramolecular Chemistry, 巻 29, 番号 1, 02.01.2017, p. 8-16.研究成果: ジャーナルへの寄稿 › 記事
}
TY - JOUR
T1 - Supramolecular dimeric structures of pyrazole-containing meso-oxo carbaphlorin analogues
AU - Ishida, Masatoshi
AU - Fujimoto, Hiroyuki
AU - Morimoto, Tatsuki
AU - Mori, Shigeki
AU - Toganoh, Motoki
AU - Shimizu, Soji
AU - Furuta, Hiroyuki
PY - 2017/1/2
Y1 - 2017/1/2
N2 - Synthesis and properties of a novel meso-oxo carbaphlorin analogue embedded with an N-free pyrazole moiety are described. The N-benzyl precursor was prepared by a [3 + 1]-MacDonald condensation of N-benzyl pyrazole dialdehyde and β-alkyl-substituted tripyrrane dicarboxylic acid and subsequent oxidation by ferric chloride. Upon deprotection of the benzyl group, the resulting N-free oxophlorin analogue formed a unique supramolecular dimer through mutual hydrogen bonding interactions between the pyrazole NH and meso-carbonyl group. The assembled behaviour was characterised by various spectroscopies, X-ray crystallographic analysis and vapour pressure osmometry. Under the similar reaction conditions, the condensation of meso-phenyl-substituted tripyrrane derivative afforded an unprecedented tetrapyrrolic macrocycle fused with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone unit at their α-pyrrolic positions. The X-ray crystallographic analysis of the macrocycle revealed a twisted core structure, and nonaromatic nature was elucidated.
AB - Synthesis and properties of a novel meso-oxo carbaphlorin analogue embedded with an N-free pyrazole moiety are described. The N-benzyl precursor was prepared by a [3 + 1]-MacDonald condensation of N-benzyl pyrazole dialdehyde and β-alkyl-substituted tripyrrane dicarboxylic acid and subsequent oxidation by ferric chloride. Upon deprotection of the benzyl group, the resulting N-free oxophlorin analogue formed a unique supramolecular dimer through mutual hydrogen bonding interactions between the pyrazole NH and meso-carbonyl group. The assembled behaviour was characterised by various spectroscopies, X-ray crystallographic analysis and vapour pressure osmometry. Under the similar reaction conditions, the condensation of meso-phenyl-substituted tripyrrane derivative afforded an unprecedented tetrapyrrolic macrocycle fused with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone unit at their α-pyrrolic positions. The X-ray crystallographic analysis of the macrocycle revealed a twisted core structure, and nonaromatic nature was elucidated.
UR - http://www.scopus.com/inward/record.url?scp=84965032394&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84965032394&partnerID=8YFLogxK
U2 - 10.1080/10610278.2016.1158408
DO - 10.1080/10610278.2016.1158408
M3 - Article
AN - SCOPUS:84965032394
VL - 29
SP - 8
EP - 16
JO - Supramolecular Chemistry
JF - Supramolecular Chemistry
SN - 1061-0278
IS - 1
ER -