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Synthesis, Structure and Complexing Properties of Receptors for Anions

Tomasz Zieliński 1Michał J. Chmielewski 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


The development of neutral receptors for recognition of anions has attracted much attention in supramolecular chemistry during recent years. Although there are many remarkable achievements in this area, the design of the efficient and selective receptors is still a challenging task. Our group has been focused on the relationship between the structure and binding properties of anion receptors, and in this communication we would like to present results of these studies.

We investigated properties of macrocyclic tetraamides type 1 derived from dipicolinic or isophthalic acid. Using these models, we found the correlation between the ring size and anion affinity, and showed undoubtedly the macrocyclic effect. Furthermore, we revealed that the weaker binding of the isophthalic-based receptors is due to the poor preorganisation of the ligands, and we showed how this obstacle can be overcome.
The other field of our interest is the application of benzopyrrole subunits as building blocks for anion receptors. In the course of these studies we examined the derivatives of indol-7-amine (2), diaminocarbazole (3) and dipyrrolonaphtalene (4). We found that replacement of aniline with indolamine can lead to over five times higher anion affinity. Bisamides of diaminocarbazole turned out to bind anions very efficiently, whereas, derivatives of dipyrrolonaphtalene could act as fluorescent sensors.


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Presentation: invited lecture at 18th Conference on Physical Organic Chemistry, Plenary session, by Janusz Jurczak
See On-line Journal of 18th Conference on Physical Organic Chemistry

Submitted: 2006-06-09 09:03
Revised:   2009-06-07 00:44