1. Supramolecular dimeric structures of pyrazole-containing meso -oxo carbaphlorin analogues.
- Author
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Ishida, Masatoshi, Fujimoto, Hiroyuki, Morimoto, Tatsuki, Mori, Shigeki, Toganoh, Motoki, Shimizu, Soji, and Furuta, Hiroyuki
- Subjects
- *
SUPRAMOLECULAR chemistry , *PYRAZOLES , *BENZYL compounds , *DICARBOXYLIC acids , *FERRIC chloride - Abstract
Synthesis and properties of a novelmeso-oxo carbaphlorin analogue embedded with anN-free pyrazole moiety are described. TheN-benzyl precursor was prepared by a [3 + 1]-MacDonald condensation ofN-benzyl pyrazole dialdehyde andβ-alkyl-substituted tripyrrane dicarboxylic acid and subsequent oxidation by ferric chloride. Upon deprotection of the benzyl group, the resultingN-free oxophlorin analogue formed a unique supramolecular dimer through mutual hydrogen bonding interactions between the pyrazole NH andmeso-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 ofmeso-phenyl-substituted tripyrrane derivative afforded an unprecedented tetrapyrrolic macrocycle fused with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone unit at theirα-pyrrolic positions. The X-ray crystallographic analysis of the macrocycle revealed a twisted core structure, and nonaromatic nature was elucidated. [ABSTRACT FROM AUTHOR]
- Published
- 2017
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