Near‐IR Absorbing J‐Aggregate of an Amphiphilic BF 2 ‐Azadipyrromethene Dye by Kinetic Cooperative Self‐Assembly
Abstract
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.
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The formation of specific self-assembled aggregates can be guided by several parameters including salt concentration, temperature, pH, and solvent.
“Alternatively, the formation of specific self-assembled aggregates can be guided by several parameters,101 including salt concentration, temperature,102,103 pH, and solvent.104,105”
From The Pursuit of Shortwave Infrared-Emitting Nanoparticles with Bright Fluorescence through Molecular Design and Excited-State Engineering of Molecular Aggregates (2022) · cites this paper as [101]
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References 40 · Cited by 212
- Authors
- Chen, Z., Liu, Y., Wagner, W., Stepanenko, V., Ren, X., Ogi, S., & Würthner, F.
- Affiliations
- Tianjin University (CN)
- University of Würzburg (DE)
- School of Chemical Engineering and Technology Collaborative Innovation Center of Chemical Science and Chemical Engineering (Tianjin) Tianjin University Tianjin 300072 China
- Corresponding author
- Chen, Zhijian
- Würthner, Frank
- Venue
- Angewandte Chemie International Edition
- Publisher
- Wiley
- Published
- 2017-03-29
- Volume
- 56
- Issue
- 21
- Pages
- 5729-5733
- ISSN
- 1433-7851 (ISSN-L)
- 1521-3773
- OpenAlex
- W2601428009
- Cited by
- 212
- References
- 40
- Citations by year
- 2026: 6 · 2025: 17 · 2024: 23 · 2023: 24 · 2022: 28 · 2021: 24 · 2020: 35 · 2019: 22 · 2018: 23 · 2017: 10
- FWCI
- 10.38
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Angewandte Chemie International Edition (publishedVersion)
- PubMed (publishedVersion)
- Funders
- National Natural Science Foundation of China (21176184)
- Bayerisches Staatsministerium für Wissenschaft, Forschung und Kunst (BPI)
- Topics
- Physical Sciences › Materials Science › Materials Chemistry › Porphyrin and Phthalocyanine Chemistry
- Physical Sciences › Materials Science › Biomaterials › Supramolecular Self-Assembly in Materials
- Physical Sciences › Materials Science › Materials Chemistry › Luminescence and Fluorescent Materials
- Keywords
- J-aggregates, near-infrared absorption, amphiphilic dyes, cooperative self-assembly, click chemistry, aggregation pathways, aggregation morphology
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