Molecules 2003, 8(7), 565-592; doi:10.3390/80700565
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,* email, 2, 2, 3 and 3
Received: 7 December 2002; in revised form: 26 June 2003 / Accepted: 27 June 2003 / Published: 15 July 2003
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
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
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MDPI and ACS Style

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.

AMA Style

Howell RC, Edwards SH, Gajadhar-Plummer AS, Kahwa IA, McPherson GL, Mague JT, White AJP, Williams DJ. Phthalimides: Supramolecular Interactions in Crystals, Hypersensitive Solution 1H-NMR Dynamics and Energy Transfer to Europium(III) and Terbium(III) States. Molecules. 2003; 8(7):565-592.

Chicago/Turabian Style

Howell, Robertha C.; Edwards, Selvin H.; Gajadhar-Plummer, Alison S.; Kahwa, Ishenkumba A.; McPherson, Gary L.; Mague, Joel T.; White, Andrew J.P.; Williams, David J. 2003. "Phthalimides: Supramolecular Interactions in Crystals, Hypersensitive Solution 1H-NMR Dynamics and Energy Transfer to Europium(III) and Terbium(III) States." Molecules 8, no. 7: 565-592.

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