Molecular Recognition of Nitro- and Cyanoarenes by Podand Diazacoronands

Adam Sobczuk 1Marcin Pawlak 1Jarosław Kalisiak 1Janusz Jurczak 2

1. Polish Academy of Sciences, Institute of Physical Chemistry, Kasprzaka 44/52, Warszawa 01-224, Poland
2. Uniwersytet Warszawski, Wydział Chemii, Warszawa, Poland


Molecular recognitions, the keystone of supramolecular chemistry [1], depends on a variety of noncovalent interaction. Among them an arene-arene interaction play a fundamental role in the selective complexation of π-neutral guests. The interaction between simple arenes compromise π-acid/base (charge-transfer), van der Walls (dispersive), and polar electrostatic (coulombic) components [2]. The understanding of electron transfer processes is essential for future progress in many diverse fields of science, spinning from biological enzymes [3] via organic synthesis [4] to optoelectronic devices [5].

In this communication we would like to present the synthesis and complexation study of O-benzylated diazacoronands of type 1.


The above-mentioned electron-rich macrocyclic donor compounds with electron-poor acceptor like nitro- and cyanoarenes, forming 1:1 charge-transfer complexes. Their formation was confirmed by NMR and UV-vis spectroscopy as well as X-ray analysis.

[1] J.-M. Lehn, Angew. Chem., Int. Ed. 1990, 29, 1304.

[2] C. A. Hunter, K. R. Lawson, C. J. Urch, J. Chem. Soc. Perkin Trans. 2 2001, 651.

[3] C. A. Hunter, J. Mol. Biol.1993, 230, 1025.

[4] J. F. Stoddart, D. J. Williams, J. Org. Chem. 1997, 62, 26.

[5] P. Günter, C. Bosshard, V. Gramlich, Adv. Mater. 1998, 10, 777.

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Presentation: poster at 18th Conference on Physical Organic Chemistry, Posters, by Adam Sobczuk
See On-line Journal of 18th Conference on Physical Organic Chemistry

Submitted: 2006-06-08 16:51
Revised:   2009-06-07 00:44
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