Journal
SUPRAMOLECULAR CHEMISTRY
Volume 29, Issue 1, Pages 8-16Publisher
TAYLOR & FRANCIS LTD
DOI: 10.1080/10610278.2016.1158408
Keywords
Porphyrin analogue; pyrazole; self-assembly; DDQ adduct
Categories
Funding
- Ministry of Education, Culture, Sports, Science and Technology, Japan [25248039, 26810024]
- Grants-in-Aid for Scientific Research [26708003, 15K13646, 15K17825, 25248039, 15H00756, 15H01001, 16K05700] Funding Source: KAKEN
Ask authors/readers for more resources
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 b-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 a-pyrrolic positions. The X-ray crystallographic analysis of the macrocycle revealed a twisted core structure, and nonaromatic nature was elucidated. [GRAPHICS] .
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available