Maurer-Chronakis K, Hager K, Hirsch A (2006)
Publication Type: Journal article, Original article
Publication year: 2006
Original Authors: Maurer K., Hager K., Hirsch A.
Publisher: Wiley-VCH Verlag
Pages Range: 3338-3347
Journal Issue: 15
The synthesis and characterisation of a new type of porphyrin-based tetrakis(Hamilton receptor) 1 is presented and the complexation of 1 with the chiral depsipeptide dendrons 7-12, with cyanuric acid functionalities as their focal points, is reported. The resulting first- to third-generation chiral supramolecular dendrimers 13-18 were characterised by NMR, UV/Vis and CD spectroscopy. Chirality transfer from the depsipeptide dendrons to the porphyrin core was demonstrated by CD spectroscopy in the case of the second- and third-generation complexes 15-18, whereas no chirality transfer and hence no diastereoselectiye formation of a chiral superstructure could be determined in the case of the first-generation systems. The intensities of the complexes' CD absorptions in the porphyrin region are inversely proportional to the size of the dendrons, pointing to a size-dependent cooperativity of the fourfold complexation of the dendrons with the more effective binding of the second-generation dendrons 9 and 10 relative to their bulkier third-generation counterparts 11 and 12. Pronounced cooperativity during the formation of the second-generation 1:L complexes (L = 9, 10) is considered to be the reason for the diastereoselective formation of a preferred chiral conformation of the Hamilton receptor 1 in the complexes 15 and 16. © Wiley-VCH Verlag GmbH & Co. KGaA, 2006.
APA:
Maurer-Chronakis, K., Hager, K., & Hirsch, A. (2006). Self-assembly and chiroptical properties of chiral dendrimers consisting of a Hamilton receptor substituted porphyrin and depsipeptide cyanurates. European Journal of Organic Chemistry, 15, 3338-3347. https://doi.org/10.1002/ejoc.200500951
MLA:
Maurer-Chronakis, Katja, Kristine Hager, and Andreas Hirsch. "Self-assembly and chiroptical properties of chiral dendrimers consisting of a Hamilton receptor substituted porphyrin and depsipeptide cyanurates." European Journal of Organic Chemistry 15 (2006): 3338-3347.
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