Hydrogen-bonded perylene bisimide J-aggregate aqua material

Chemical Science
Vincenzo GrandeFrank Würthner

Abstract

A new twelvefold methoxy-triethyleneglycol-jacketed tetraphenoxy-perylene bisimide (MEG-PBI) amphiphile was synthesized that self-assembles into two types of supramolecular aggregates in water: red-coloured aggregates of low order and with weak exciton coupling among the PBIs and blue-coloured strongly coupled J-aggregates consisting of a highly ordered hydrogen-bonded triple helix of PBIs. At room temperature this PBI is miscible with water at any proportions which enables the development of robust dye aggregates in solution, in hydrogel states and in lyotropic liquid crystalline states. In the presence of 60-95 wt% water, self-standing coloured hydrogels exhibit colour changes from red to blue accompanied by a fluorescence light-up in the far-red region upon heating in the range of 30-50 °C. This phenomenon is triggered by an entropically driven temperature-induced hydrogen-bond-directed slipped stacking arrangement of the MEG-PBI chromophores within structurally well-defined J-aggregates. This versatile aqua material is the first example of a stable PBI J-aggregate in water. We anticipate that this study will open a new avenue for the development of biocompatible functional materials based on self-assembled dyes and inspire ...Continue Reading

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Citations

Aug 10, 2019·Physical Chemistry Chemical Physics : PCCP·Elisa AlloaSophia C Hayes
Nov 27, 2019·Chemical Communications : Chem Comm·José Augusto BerrocalAnja R A Palmans
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Dec 9, 2020·Accounts of Chemical Research·Markus Hecht, Frank Würthner
Dec 10, 2019·Journal of the American Chemical Society·Kotagiri Venkata RaoTakuzo Aida
Dec 28, 2019·Biomacromolecules·Eduardo CastellanosAntonio Costa
Nov 12, 2020·Journal of the American Chemical Society·Mathijs F J MabesooneE W Meijer
Oct 2, 2021·Chemistry : a European Journal·Robert S Wilson-KovacsCharl F J Faul
Dec 11, 2021·Journal of Materials Chemistry. B, Materials for Biology and Medicine·Prabhpreet SinghSatwinderjeet Kaur

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Methods Mentioned

BETA
fluorescence spectroscopy
atomic force microscopy
AFM
NMR
optical microscopy
differential scanning calorimetry
X-ray
polarized optical microscopy

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