期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 144, 期 14, 页码 6343-6348出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.2c00156
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资金
- Queensland University of Technology (QUT)
- Centre for Materials Science
- Australian Research Council (ARC)
- ARC
This article introduces a novel photochemically active compound, PyPy, which possesses a pH-active moiety to control the reaction pathways. By incorporating PyPy into the design of single-chain nanoparticles, the repulsive forces can be overcome and the halochromic shift can be utilized to induce chemical reactions.
We introduce a new photochemically active compound, i.e., pyridinepyrene (PyPy), entailing a pH-active moiety that effects a significant halochromic shift into orange-light (lambda = 590 nm) activatable photoreactivity while concomitantly exerting control over its reaction pathways. With blue light (lambda = 450 nm) in neutral to basic pH, a [2 + 2] photocycloaddition can be triggered to form a cyclobutene ring in a reversible fashion. If the pH is decreased to acidic conditions, resulting in a halochromic absorption shift, photocycloaddition on the small-molecule level is blocked due to repulsive interactions and exclusive trans-cis isomerization is observed. Through implementation of PyPy into the confined environment of a single-chain nanoparticle (SCNP) design, one can overcome the repulsive forces and exploit the halochromic shift for orange light (lambda = 590 nm)-induced cycloaddition and formation of macromolecular three-dimensional (3D) architectures.
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