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Molecules 2003, 8(7), 565-592; doi:10.3390/molecules8070565
Article

Phthalimides: Supramolecular Interactions in Crystals, Hypersensitive Solution 1H-NMR Dynamics and Energy Transfer to Europium(III) and Terbium(III) States

1, 1, 1, 1,* , 2, 2, 3 and 3
1 Department of Chemistry, University of the West Indies, Mona Campus, Kingston 7, Jamaica, West Indies 2 Department of Chemistry, Tulane University, New Orleans, Louisiana 70118, USA 3 Chemical Crystallography Laboratory, Department of Chemistry, Imperial College of Science, Technology and Medicine, South Kensington, London SW7 2AY, UK
* Author to whom correspondence should be addressed.
Received: 7 December 2002 / Revised: 26 June 2003 / Accepted: 27 June 2003 / Published: 15 July 2003
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Abstract

Detailed crystal structures and 1H-NMR characteristics of some alkylaminephthalimides, including dendritic polyphthalimides, are reported. These investigations were undertaken in order to obtain a better understanding of the relationship between solid-state supramolecular interactions, their persistence in solution and associated dynamics of magnetically hypersensitive phthalimide aromatic AA'BB'-AA'XX' proton NMR resonances. Some alkylamine phthalimides feature folded molecular geometries, which we attribute to n-π interactions among proximal amine-phthalimide sites; those alkylamine-phthalimides that have no possibility for such interactions feature fully extended phthalimide functionalities. Accordingly, alkylamine phthalimide compounds with folded solid-state geometries feature solvent and temperature dependent hypersensitive AA'BB'-AA'XX' 1H-NMR line profiles, which we attribute to the n-π interactions. Luminescence of Eu3+(5D0) and Tb3+(5D4) states show well defined metal ion environments in their complexes with dendritic phthalimides, as well as relatively weak phthalimide-lanthanide(III) interactions.
Keywords: Phthalimides; n-π interactions; dynamic NMR chemical shifts; lanthanides luminescence Phthalimides; n-π interactions; dynamic NMR chemical shifts; lanthanides luminescence
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Howell, R.C.; Edwards, S.H.; Gajadhar-Plummer, A.S.; Kahwa, I.A.; McPherson, G.L.; Mague, J.T.; White, A.J.P.; Williams, D.J. Phthalimides: Supramolecular Interactions in Crystals, Hypersensitive Solution 1H-NMR Dynamics and Energy Transfer to Europium(III) and Terbium(III) States. Molecules 2003, 8, 565-592.

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