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Issue 10, 2013
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Synthesis of helically twisted [1 + 1]macrocycles assisted by amidinium–carboxylate salt bridges and control of their chiroptical properties

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Abstract

A series of optically active, helically twisted [1 + 1]macrocycles connected via o-, m-, and p-linkages (o-2, m-2, and p-2) 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.

Graphical abstract: Synthesis of helically twisted [1 + 1]macrocycles assisted by amidinium–carboxylate salt bridges and control of their chiroptical properties

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Publication details

The article was received on 22 Oct 2012, accepted on 19 Nov 2012 and first published on 20 Nov 2012


Article type: Paper
DOI: 10.1039/C2OB27054D
Citation: Org. Biomol. Chem., 2013,11, 1614-1623
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    Synthesis of helically twisted [1 + 1]macrocycles assisted by amidinium–carboxylate salt bridges and control of their chiroptical properties

    Y. Nakatani, Y. Furusho and E. Yashima, Org. Biomol. Chem., 2013, 11, 1614
    DOI: 10.1039/C2OB27054D

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