ISMSC 2007 - Università degli Studi di Pavia

PSA 81
Reaction of phthalic aldehydes with a,w-diamines for generation of Dynamic
Combinatorial Libraries
Magdalena Jarosz, a Janusz Jurczak a,b
a) Department of Chemistry, Warsaw University, Pasteura 1, 02-093 Warsaw, Poland
b) Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52,
01-224 Warsaw, Poland
Dynamic Combinatorial Chemistry[1] [2] explores various reversible reactions and thus is a
useful tool in supramolecular chemistry. As a result of such reaction the dynamic combinatorial
library, consisting of various components, is obtained. By changing the conditions, e.g.
templating cation, distribution of obtained products can be changed favouring the desired one.
We present our studies on imination reaction between phthalic aldehydes and three different in
length linear diamines exemplified by that shown in Scheme 1.
Scheme 1
Dynamic Combinatorial Libraries of obtained macrocyclic imines were analysed using
electrospray ionization mass spectrometry (ESI-MS). The libraries were "frozen" by the
reduction reaction (NaBH4) and obtained amines protected and analysed by HPLC technique.
[1] J.M. Lehn, Science, 2002, 295, 2400-2403
[2] S. Otto, R.L.E Furlan, J.K.M Sanders, Drug Discovery Today, 2002, 7, 117-125
Chemical Detection of Explosives
Jan O. Jeppesen, 1 Kent A. Nielsen, 1 Lise G. Jensen, 1 Andrew D. Bond, 1
Won-Seob Cho, 2 Vincent M. Lynch, 2 and Jonathan L. Sessler 2
PSA 82
1
The University of Southern Denmark, Odense University, Campusvej 55, 5230 Odense M,
Denmark; e-mail: joj@chem.sdu.dk
2
The University of Texas at Austin, Austin, 1 University Station-A5300, Texas 78712-0165, USA
The advent of supramolecular chemistry [1] has stimulated the interest in developing
chemosensors capable of recognizing [2] specific chemical species through weak, non-covalent
interactions. Calix[4]pyrroles [3] – first synthesized in the nineteenth century by Baeyer – are
endowed with four pyrrole NH hydrogen bond functionalities and have recently received
extensively attention as receptors for anionic and neutral substrates. The incorporation of redoxactive
components into chemosensors is one means of enhancing the recognition process via,
e.g., increased donor-acceptor interactions. In this context, the use of tetrathiafulvalene [4] (TTF)
appears particularly attractive and a calix[4]pyrrole incorporating four appended TTF units has
recently been synthesized. [5,6] It will be demonstrated, that this tetra(TTF)-calix[4]pyrrole is an
excellent chemosensor capable of detecting explosives – such as trinitrotoluene (TNT)
commonly used in landmines – through a simple color change from yellow to green (see figure).
[1] J.-M. Lehn, Supramolecular Chemistry, VCH, Weinheim, Germany, 1995.
[2] (a) P. D. Beer, P. A. Gale Angew. Chem. Int. Ed. 2001, 40, 486−516. (b) K. A. Nielsen, J.
O. Jeppesen, E. Levillain, J. Becher Angew. Chem. Int. Ed. 2003, 42, 187–191.
[3] J. L. Sessler, P. A. Gale in The Porphyrin Handbook, Vol. 6 (Eds.: K. M. Kadish, K. M.
Smith, R. Guilard), Academic Press, San Diego, 2000, pp. 257–278.
[4] (a) J. L. Segura, N. Martín Angew. Chem., Int. Ed. 2001, 40, 1372–1409.
(b) J. O. Jeppesen, J. Becher Eur. J. Org. Chem. 2003, 3245–3266.
[5] K. A. Nielsen, W.-S. Cho, J. O. Jeppesen, V. M. Lynch, J. Becher, J. L. Sessler J. Am.
Chem. Soc. 2004, 126, 16296–16297.
[6] K. A. Nielsen, W.-S. Cho, J. Lyskawa, E. Levillain, V. M. Lynch, J. L. Sessler, J. O.
Jeppesen J. Am. Chem. Soc. 2006, 128, 2444–2451.