Synthesis and properties of polyaromatic dendrimers possessing a repetitive amide-ester coupling sequence

Romagnoli, B., Ashton, P.R., Harwood, L.M. ORCID: https://orcid.org/0000-0002-8442-7380, Philp, D., Price, D.W., Smith, M.H. and Hayes, W. ORCID: https://orcid.org/0000-0003-0047-2991 (2003) Synthesis and properties of polyaromatic dendrimers possessing a repetitive amide-ester coupling sequence. Tetrahedron, 59 (22). pp. 3975-3988. ISSN 0040-4020 doi: 10.1016/s0040-4020(03)00466-6

Abstract/Summary

A series of novel polyaromatic dendrimers that feature tris-(2-ethylamino)amine as the central core unit has been synthesized up to the third generation by employing a convergent growth strategy. The building blocks 1,3-diamino-2-hydroxypropane and 4-carboxybenzaldehyde were used for dendron construction, a process that involved the cyclic repetition of esterification, oxidation and selective amidation steps. Molecular modelling of this class of dendrimers has been used to predict potential solution state conformations employing molecular mechanics and molecular dynamic simulations. In addition, the results of preliminary metal binding studies using the first generation dendritic system are also outlined. (C) 2003 Elsevier Science Ltd. All rights reserved.