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Near‐IR Absorbing J‐Aggregate of an Amphiphilic BF 2 ‐Azadipyrromethene Dye by Kinetic Cooperative Self‐Assembly
Author(s) -
Chen Zhijian,
Liu Yong,
Wagner Wolfgang,
Stepanenko Vladimir,
Ren Xiangkui,
Ogi Soichiro,
Würthner Frank
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201701788
Subject(s) - j aggregate , amphiphile , transmission electron microscopy , self assembly , absorption (acoustics) , laser linewidth , metastability , spectroscopy , absorption spectroscopy , materials science , aggregate (composite) , infrared spectroscopy , chemistry , photochemistry , analytical chemistry (journal) , nanotechnology , molecule , optics , polymer , organic chemistry , copolymer , physics , laser , quantum mechanics , composite material
A new amphiphilic BF 2 ‐azadipyrromethene (aza‐BODIPY) dye 1 has been synthesized using a Cu I ‐catalyzed “click” reaction. For this dye, two self‐assembly pathways that lead to different type of J‐aggregates with distinct near‐infrared optical properties have been discovered. The metastable off‐pathway product displays a broad, structureless absorption band while the thermodynamically stable on‐pathway aggregate exhibits the characteristic spectral features of a J‐aggregate, that is, red‐shifted intense absorption band with significantly narrowed linewidth. The morphology and structure of the aggregates were studied by atomic force microscopy, transmission and scanning electron microscopy. The aggregation processes of 1 were investigated by temperature‐ and concentration‐dependent UV/Vis spectroscopy and evaluated by models for cooperative self‐assembly.