Amphiphilic Perylene-Calix[4]arene Hybrids: Synthesis and Tunable Self-Assembly

Rodler F, Schade B, Jaeger CM, Backes S, Hampel F, Boettcher C, Clark T, Hirsch A (2015)

Publication Status: Published

Publication Type: Journal article

Publication year: 2015

Journal

Publisher: American Chemical Society

Book Volume: 137

Pages Range: 3308-3317

Journal Issue: 9

DOI: 10.1021/ja512048t

Abstract

The first highly water-soluble perylene-calix[4]arene hybrid with the calixarene scaffold acting as a structure-determining central platform is presented. In this tetrahedrally shaped amphiphilic architecture the hydrophilic and hydrophobic subunits are oriented at the opposite side of the calixarene platform. The hydrophobic part contains the two perylene diimide moieties, which enable strong pi-pi interactions in self-assembly processes. Two hydrophilic Newkome-type dendrons provide sufficient water solubility at slightly basic conditions. The tetrahedrally shaped amphiphile displays an unprecedented aggregation behavior down to concentrations as low as 10(-7) mol L-1. The intriguing self-assembly process of the compound in water as well as under changed polarity conditions, achieved by addition of THF, could be monitored by the complemented use of cryogenic transmission electron microscopy (cryo-TEM), UV-vis spectroscopy, and fluorescence spectroscopy. Molecular-dynamics and molecular modeling simulations helped in understanding the interplay of supramolecular and optical behavior.

Authors with CRIS profile

Additional Organisation(s)

Involved external institutions

University of Nottingham United Kingdom (GB) Freie Universität Berlin Germany (DE)

How to cite

APA:

Rodler, F., Schade, B., Jaeger, C.M., Backes, S., Hampel, F., Boettcher, C.,... Hirsch, A. (2015). Amphiphilic Perylene-Calix[4]arene Hybrids: Synthesis and Tunable Self-Assembly. Journal of the American Chemical Society, 137(9), 3308-3317. https://dx.doi.org/10.1021/ja512048t

MLA:

Rodler, Fabian, et al. "Amphiphilic Perylene-Calix[4]arene Hybrids: Synthesis and Tunable Self-Assembly." Journal of the American Chemical Society 137.9 (2015): 3308-3317.

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