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Living Supramolecular Polymerization of a Perylene Bisimide Dye into Fluorescent J‐Aggregates
Author(s) -
Wagner Wolfgang,
Wehner Marius,
Stepanenko Vladimir,
Ogi Soichiro,
Würthner Frank
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201709307
Subject(s) - perylene , polymerization , fluorescence , supramolecular chemistry , monomer , photochemistry , chemistry , intermolecular force , j aggregate , hydrogen bond , molecule , polymer , organic chemistry , physics , quantum mechanics
The self‐assembly of a new perylene bisimide (PBI) organogelator with 1,7‐dimethoxy substituents in the bay position affords non‐fluorescent H‐aggregates at high cooling rates and fluorescent J‐aggregates at low cooling rates. Under properly adjusted conditions, the kinetically trapped “off‐pathway” H‐aggregates are transformed into the thermodynamically favored J‐aggregates, a process that can be accelerated by the addition of J‐aggregate seeds. Spectroscopic studies revealed a subtle interplay of π–π interactions and intra‐ and intermolecular hydrogen bonding for monomeric, H‐, and J‐aggregated PBIs. Multiple polymerization cycles initiated from the seed termini demonstrate the living character of this chain‐growth supramolecular polymerization process.