Issue 4, 2017

Template-directed synthesis of linear porphyrin oligomers: classical, Vernier and mutual Vernier

Abstract

Three different types of template-directed syntheses of linear porphyrin oligomers are presented. In the classical approach the product has the same number of binding sites as the template, whereas in Vernier reactions the product has the lowest common multiple of the numbers of binding sites in the template and the building block. Mutual Vernier templating is like Vernier templating except that both strands of the Vernier complex undergo coupling simultaneously, so that it becomes impossible to say which is the ‘template’ and which is the ‘building block’. The template-directed synthesis of monodisperse linear oligomers is more difficult than that of cyclic oligomers, because the products of linear templating have reactive ends. All three types of templating are demonstrated here, and used to prepare a nickel(II) porphyrin dodecamer with 4-pyridyl substituents on all twelve porphyrin units. The stabilities and cooperativities of the double-strand complexes involved in these reactions were investigated by UV-vis-NIR titration. The four-rung ladder duplex has a stability constant of about 2 × 1018 M−1 in dichloromethane at 298 K.

Graphical abstract: Template-directed synthesis of linear porphyrin oligomers: classical, Vernier and mutual Vernier

Supplementary files

Article information

Article type
Edge Article
Submitted
06 12月 2016
Accepted
20 1月 2017
First published
20 1月 2017
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2017,8, 2729-2740

Template-directed synthesis of linear porphyrin oligomers: classical, Vernier and mutual Vernier

N. Kamonsutthipaijit and H. L. Anderson, Chem. Sci., 2017, 8, 2729 DOI: 10.1039/C6SC05355F

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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