Supramolecular assembly of self-labeled amphicalixarenes

Chemistry : a European Journal
Miriam S BechererAndreas Hirsch

Abstract

The synthesis and precise supramolecular organization of new amphicalixarene 4 bearing four rodlike aligned fluorescent terephthalic benzamide moieties in the upper rim is reported. The aggregation of 4 was monitored by a combination of fluorescence, conductometry, and cryo-TEM measurements at different pH values and revealed significant structural differences. Most interestingly, we found that exactly 12 molecules of 4 assemble to form a spherical and structurally persistent micelle at pH 7, which coexists with rodlike micelles. In contrast to other examples of structurally defined micelles reported previously, this new type of self-labeled amphiphile serves as a fluorescence reporter with the terephthalic units additionally providing an extended cavity structure in the hydrophilic part, which facilitates the inclusion of guest molecules. In addition to the observed formation of well-defined micelles, the other highly important finding from this study is the fact that guest molecules directly influence the micellar organization because they can interact with both the free amphiphiles below the critical micelle concentration (cmc) or the micellar aggregate itself. These two types of interactions are especially pronounced in the...Continue Reading

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Citations

Dec 17, 2015·Chemical Reviews·Bala N S ThotaRainer Haag
Oct 11, 2016·Langmuir : the ACS Journal of Surfaces and Colloids·Maxim VarenikOren Regev
May 12, 2017·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Khalid KhanYahia Mabkhot
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May 22, 2018·Macromolecular Bioscience·Suchita PrasadSunil K Sharma
Oct 30, 2015·Angewandte Chemie·Stefano TommasonePlacido Neri
Jul 27, 2010·Chemistry : a European Journal·Karin RosenlehnerAndreas Hirsch
Aug 28, 2010·Angewandte Chemie·Immanuel Willerich, Franziska Gröhn
Feb 11, 2011·Chemistry : a European Journal·K YoosafNicola Armaroli
Dec 2, 2011·Organic & Biomolecular Chemistry·Hong HuangYan-Song Zheng
Apr 20, 2011·Chemistry : a European Journal·Roman V RodikYves Mély
Apr 27, 2013·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Andreas T HaedlerHans-Werner Schmidt
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Jul 16, 2019·Chemical Reviews·Rajesh KumarJong Seung Kim

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