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Inclusion of alkyl nitriles by tetra-armed cyclens with styrylmethyl groups

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Abstract

Synthesis of tetra-armed cyclens (2a–2e), with substituted styrylmethyl groups as side-arms, and their Ag+ complexes is reported. The Ag+ complex with a tetra styrylmethyl-armed cyclen (2a) incorporates alkyl nitriles in a pseudo-cavity formed by the four styrylmethyl side-arms. This prompted us to apply this system to the determination of the absolute configurations of chiral nitriles with low [α]D and low circular dichroism (CD) intensity. In the CD spectra of the 2a/Ag+ complex, (S)- and (R)-G1 did not show a specific Cotton effect, while when chiral nitriles were added to the 2a/Ag+ complex, drastic spectral changes were observed. The (S)-G1@2a/Ag+ system exhibited first a negative and then a positive Cotton effect, whereas the (R)-G1@2a/Ag+ system showed the mirror image of the Cotton effect of (S)-G1@2a/Ag+. We have, therefore, demonstrated a new technique for determining the absolute configurations of weak optical rotation molecules using the Ag+ complex with 2a.

Graphical abstract: Inclusion of alkyl nitriles by tetra-armed cyclens with styrylmethyl groups

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Article information


Submitted
30 Jan 2020
Accepted
05 Feb 2020
First published
12 Feb 2020

Dalton Trans., 2020, Advance Article
Article type
Paper

Inclusion of alkyl nitriles by tetra-armed cyclens with styrylmethyl groups

H. Ju, H. Tenma, M. Iwase, E. Lee, M. Ikeda, S. Kuwahara and Y. Habata, Dalton Trans., 2020, Advance Article , DOI: 10.1039/D0DT00335B

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