Piperazine Bridged Resorcinarene Cages

Ngong Kodiah Beyeh; Arto Valkonen; Kari Rissanen

doi:10.1021/ol100407f

Piperazine Bridged Resorcinarene Cages

Ngong Kodiah Beyeh, Arto Valkonen, Kari Rissanen

Not published at Aalto University

Research output: Contribution to journal › Article › Scientific › peer-review

25 Citations (Scopus)

Abstract

The one-pot Mannich condensation of resorcinarenes with piperazine and an excess of formaldehyde under high dilution conditions results in a helical cage, namely, a covalently linked dimer of two resorcinarenes connected via four piperazine bridges in yields ranging from 20 to 40%. The compounds were analyzed by NMR spectroscopy, ESI mass spectrometry, and single crystal X-ray diffraction. The helical cages can encapsulate small guest molecules by adapting the cavity volume by changing the helical pitch according to the guest size.

Original language	English
Pages (from-to)	1392–1395
Journal	ORGANIC LETTERS
Volume	12
Issue number	7
DOIs	https://doi.org/10.1021/ol100407f
Publication status	Published - Mar 2010
MoE publication type	A1 Journal article-refereed

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10.1021/ol100407f

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title = "Piperazine Bridged Resorcinarene Cages",

abstract = "The one-pot Mannich condensation of resorcinarenes with piperazine and an excess of formaldehyde under high dilution conditions results in a helical cage, namely, a covalently linked dimer of two resorcinarenes connected via four piperazine bridges in yields ranging from 20 to 40%. The compounds were analyzed by NMR spectroscopy, ESI mass spectrometry, and single crystal X-ray diffraction. The helical cages can encapsulate small guest molecules by adapting the cavity volume by changing the helical pitch according to the guest size.",

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AU - Rissanen, Kari

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N2 - The one-pot Mannich condensation of resorcinarenes with piperazine and an excess of formaldehyde under high dilution conditions results in a helical cage, namely, a covalently linked dimer of two resorcinarenes connected via four piperazine bridges in yields ranging from 20 to 40%. The compounds were analyzed by NMR spectroscopy, ESI mass spectrometry, and single crystal X-ray diffraction. The helical cages can encapsulate small guest molecules by adapting the cavity volume by changing the helical pitch according to the guest size.

AB - The one-pot Mannich condensation of resorcinarenes with piperazine and an excess of formaldehyde under high dilution conditions results in a helical cage, namely, a covalently linked dimer of two resorcinarenes connected via four piperazine bridges in yields ranging from 20 to 40%. The compounds were analyzed by NMR spectroscopy, ESI mass spectrometry, and single crystal X-ray diffraction. The helical cages can encapsulate small guest molecules by adapting the cavity volume by changing the helical pitch according to the guest size.

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