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Org Biomol Chem. 2013 Feb 13;11(10):1614-23. doi: 10.1039/c2ob27054d.

Synthesis of helically twisted [1 + 1]macrocycles assisted by amidinium-carboxylate salt bridges and control of their chiroptical properties.

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1
Department of Molecular Design and Engineering, Graduate School of Engineering, Nagoya University, Nagoya 464-8603, Japan.

Abstract

A series of optically active, helically twisted [1 + 1]macrocycles connected via o-, m-, and p-linkages (o-, m-, and p-) was prepared from the corresponding linear duplexes stabilized by complementary amidinium-carboxylate salt bridges bearing two arms with terminal vinyl groups at both ends through the ring-closing metathesis reaction in the good yields of 67, 92, and 96%, respectively. The chiroptical properties of the macrocycles were dependent on the linker geometries and could be controlled by acid-base interactions and zinc coordination, the changes in which were detected by their CD and absorption spectral changes and fluorescence colors.

PMID:
23223850
DOI:
10.1039/c2ob27054d
[Indexed for MEDLINE]
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