Angewandte Chemie - International Edition
Angewandte Chemie - International Edition
5 years ago

Near-IR Absorbing J-Aggregate of an Amphiphilic BF2-Azadipyrromethene Dye by Kinetic Cooperative Self-Assembly

Near-IR Absorbing J-Aggregate of an Amphiphilic BF2-Azadipyrromethene Dye by Kinetic Cooperative Self-Assembly
Vladimir Stepanenko, Zhijian Chen, Xiangkui Ren, Soichiro Ogi, Yong Liu, Frank Würthner, Wolfgang Wagner
A new amphiphilic BF2-azadipyrromethene (aza-BODIPY) dye 1 has been synthesized using a CuI-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. Chlorophyll analog: An amphiphilic BF2-azadipyrromethene (aza-BODIPY) dye 1 forms two types of aggregates with distinct optical properties and nanoscale morphologies through competing cooperative self-assembly pathways. The observed rod-like morphology and exciton characteristics for the aza-BODIPY-based J-aggregates are comparable to those of natural chlorophyll dye assemblies.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201701788

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