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Solvent‐ and Guest‐Responsive Self‐Assembly of Hamilton Receptor Tethered Bis(merocyanine) Dyes
Author(s) -
Schmidt Ralf,
Uemura Shinobu,
Würthner Frank
Publication year - 2010
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201002159
Subject(s) - merocyanine , supramolecular chemistry , self assembly , chemistry , micelle , dynamic light scattering , amphiphile , hydrogen bond , barbituric acid , supramolecular polymers , solvent , molecule , photochemistry , polymer , materials science , copolymer , nanotechnology , organic chemistry , aqueous solution , nanoparticle
A novel supramolecular building block ( 8 ) that consists of a Hamilton receptor and two merocyanine dyes has been synthesized, and the self‐assembly based on orthogonal hydrogen bonding and dipolar interactions has been studied in detail. Different self‐assembled species, including oligomers, polymers, and inverted micelles could be observed upon variation of the solvent polarity and the concentration. Moreover, this system is highly responsive toward molecular stimuli such as merocyanine molecules with the barbituric acid motif that are bound by the Hamilton receptors. Detailed UV/Vis absorption studies provided insight into isodesmic or cooperative steps during the self‐assembly of 8 into different species. The size of the aggregates in solution and the morphology on substrates have been explored by a combination of dynamic light scattering (DLS), atomic force microscopy (AFM), and TEM investigations.