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Access through your institution Buy or subscribe The colourless imidazolyl-quinoline derivatives 1 and 2 are prepared using a Debus−Radziszewski method, which proves applicable to
phenanthrene- and phenanthroline-based precursors as well as a range of functionalized anilines, where X = H, OMe, Cl and Br (pictured). Following ultraviolet (UV) irradiation of 1 in a
mixed dichloromethane and methanol solution for 24 h, a dark purple species, 3, is obtained in 73% yield. Similarly, 2 could be converted to 4 (bright red species) in 69–93% yields.
Crystallographic analysis of 4 (where X = H) confirms the 1,4-aryl transfer reaction. The absorption and emission of the zwitterionic products 3 and 4 are substantially red-shifted compared
to 1 and 2, which can be explained by the extended _π_-conjugation on the quinoline moiety. Additionally, testing the absorbance of 1 and 3 in a range of solvents reveals that an increase in
solvent polarity leads to a blue shift in the absorption bands, which for 3, follows the trend of negative solvatochromism generally found in zwitterionic chromophores. This is a preview of
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during checkout ADDITIONAL ACCESS OPTIONS: * Log in * Learn about institutional subscriptions * Read our FAQs * Contact customer support AUTHOR INFORMATION AUTHORS AND AFFILIATIONS * Nature
Synthesis https://www.nature.com/natsynth/ Peter W. Seavill Authors * Peter W. Seavill View author publications You can also search for this author inPubMed Google Scholar CORRESPONDING
AUTHOR Correspondence to Peter W. Seavill. RIGHTS AND PERMISSIONS Reprints and permissions ABOUT THIS ARTICLE CITE THIS ARTICLE Seavill, P.W. Photoinduced aryl transfer. _Nat. Synth_ 2, 805
(2023). https://doi.org/10.1038/s44160-023-00402-7 Download citation * Published: 24 August 2023 * Issue Date: September 2023 * DOI: https://doi.org/10.1038/s44160-023-00402-7 SHARE THIS
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