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Amphiphilic Pyrene‐Functionalized Dendrons: Synthesis and Intermolecular Interactions
Author(s) -
Ebel Alexander,
Donaubauer Wolfgang,
Hampel Frank,
Hirsch Andreas
Publication year - 2007
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200700127
Subject(s) - chemistry , amphiphile , stacking , pyrene , hydrogen bond , perylene , intermolecular force , micelle , dendrimer , supramolecular chemistry , aqueous solution , molecule , fluorescence , fluorescence spectroscopy , photochemistry , combinatorial chemistry , organic chemistry , copolymer , polymer , physics , quantum mechanics
The synthesis of new functional amphiphiles 4 and 7 synthesized by DCC coupling of pyrenebutyric acid with first‐ and second‐generation Newkome‐type aminodendrons is reported. The crystal structure of the free amphiphilic tricarboxylic acid 4 exhibits efficient and cooperative usage of all possible hydrogen‐bonding sites as well as π‐stacking interactions. In contrast, no face‐to‐face π‐stacking is observed in the single‐crystal structure of the tert‐ butyl‐protected precursor molecule 3 . As determined by DOSY‐NMR spectroscopy, the second‐generation amphiphile 7 forms small micelles in aqueous solutions with a diameter of about 4 nm. Absorption and fluorescence spectroscopic investigations show that amphiphile 7 is able to promote the transfer of the apolar perylene dye 8 into the aqueous phase. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)