Naphthalenediimides with Cyclic Oligochalcogenides in Their Core
Inga Shybeka1, Alexander Aster1, Yangyang Cheng1
1School of Chemistry and Biochemistry, University of Geneva, Geneva, Switzerland.
Chemistry (Weinheim an Der Bergstrasse, Germany)
|October 2, 2020
Summary
Novel Naphthalenediimides (NDIs) featuring cyclic trisulfides exhibit unique light absorption and emission properties. These NDI-trisulfanes undergo photoinduced ring contraction, offering new possibilities for functional materials and artificial photosystems.
Area of Science:
- Organic Chemistry
- Materials Science
- Photochemistry
Background:
- Naphthalenediimides (NDIs) are versatile scaffolds with broad applications in functional systems.
- Exploration of core-substituted NDIs is ongoing to discover novel properties.
Purpose of the Study:
- To synthesize and characterize NDI derivatives with cyclic trisulfide (trisulfane) cores.
- To investigate the photophysical properties and photoinduced transformations of these novel NDI-trisulfanes.
Main Methods:
- Synthesis of NDI core-substituted with cyclic trisulfides.
- Spectroscopic analysis (absorption and emission) to determine photophysical properties.
- Photochemical studies to observe ring contraction and spectral shifts.
Main Results:
- NDI-trisulfanes absorb at 668 nm and emit at 801 nm.
- Irradiation at <475 nm induces ring contraction to disulfides (dithietes) with a blueshift to 492 nm.
- Intramolecular 1,5-chalcogen bonds contribute to significant red-shifts.
Conclusions:
- Cyclic oligochalcogenides (COCs) in NDI cores offer tunable photophysical properties.
- These COC-NDIs show rapid ring-opening and strong retention on thiol affinity columns.
- Potential applications include artificial photosystems and thiol-mediated cellular uptake.
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