AI Article Synopsis
- A series of BODIPY derivatives with α- and β-ethynyl substituents were created using a gold(I)-catalyzed reaction that selectively adds ethynyl groups to dipyrromethane.
- The positioning of the ethynyl substituents affects the photophysical characteristics of these compounds, with an increase in substituents leading to longer-wavelength absorbance and fluorescence.
- This synthesis approach allows researchers to fine-tune the light-absorbing properties of BODIPY dyes, making it useful for developing advanced materials in photonics and electronic applications.
Article Abstract
A series of α- and β-ethynyl-substituted BODIPY derivatives (, , , ) were synthesized by gold(I)-catalyzed direct C-H alkynylation reactions of dipyrromethane and BODIPY, respectively, with ethynylbenziodoxolone (EBX) in a regioselective manner. Depending on the position of the ethynyl substituent in the BODIPY skeleton, the photophysical properties of the resulting α- and β-substituted BODIPYs are notably altered. The lowest S-S transition absorbance and fluorescence bands are both bathochromically shifted as the number of substituents increases, while the emission quantum yields of the β-ethynylated derivatives are significantly lower than those of α-ethynylated ones. The current method should be useful for fine-tuning of the photophysical properties of BODIPY dyes as well as for constructing BODIPY-based building cores for functional π-materials.
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7136566 | PMC |
| http://dx.doi.org/10.3762/bjoc.16.53 | DOI Listing |
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