Synthesis and aggregation properties of water-soluble newkome-dendronized perylenetetracarboxdiimides
Schmidt C, Boettcher C, Hirsch A (2007)
Publication Type: Journal article, Original article
Publication year: 2007
Journal
Original Authors: Schmidt C.D., Böttcher C., Hirsch A.
Publisher: Wiley-VCH Verlag
Pages Range: 5497-5505
Journal Issue: 33
Abstract
The synthesis and characterization of three highly water-soluble perylenetetracarboxdiimide ("perylene bisimide", PBI) dyes 1 and 2b is presented. The water solubility is provided by peripheral dendronization with 1G- and 2G-Newkome dendrons. The aggregation behaviour of these amphiphiles in water and that of their tert-butyl-protected precursor molecules 3 and 4 in organic solvents was investigated by UV/Vis- and fluorescence spectroscopy. The symmetric 1G-dendronized dye la forms aggregates more easily than its 2G-counterpart 1b. The asymmetric derivatives 2b reveals pronounced aggregation properties due to the presence of both a 2G-dendron and a flexible and non-bulky dodecyl substituent. The 1G-analogue 2a is insoluble in water as a result of insufficient overall hydrophilicity caused by only one 1G-Newkome dendron. Within the series of water-soluble perylenes 1 and 2b the asymmetric derivative 2b forms the most regularly shaped micelles in water (pH = 7.2) with a mean diameter of 16 nm as demonstrated by transition electron microscopy (TEM). The bola-amphiphiles 1a and 1b form a distribution of smaller aggregates on average with less defined shape. © Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
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APA:
Schmidt, C., Boettcher, C., & Hirsch, A. (2007). Synthesis and aggregation properties of water-soluble newkome-dendronized perylenetetracarboxdiimides. European Journal of Organic Chemistry, 33, 5497-5505. https://dx.doi.org/10.1002/ejoc.200700567
MLA:
Schmidt, Cordula, Christoph Boettcher, and Andreas Hirsch. "Synthesis and aggregation properties of water-soluble newkome-dendronized perylenetetracarboxdiimides." European Journal of Organic Chemistry 33 (2007): 5497-5505.
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