The Cascade Reactions of Indigo with Propargyl Substrates for Heterocyclic and Photophysical Diversity
McCosker, Patrick M., Butler, Nicholas M., Shakoori, Alireza, Volland, Michel K., Perry, Matthew, Mullen, Jesse W., Willis, Anthony C., Clark, Timothy, Bremner, John B., Guldi, Dirk M., and Keller, Paul A. (2021) The Cascade Reactions of Indigo with Propargyl Substrates for Heterocyclic and Photophysical Diversity. Chemistry: A European Journal, 27 (11). pp. 3708-3721.
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Abstract
The synthesis of structurally diverse heterocycles for chemical space exploration was achieved via the cascade reactions of indigo with propargylic electrophiles. New pyrazinodiindolodione, naphthyridinedione, azepinodiindolone, oxazinoindolone and pyrrolodione products were prepared in one pot reactions by varying the leaving group (-Cl, -Br, -OMs, -OTs) or propargyl terminal functionality (-H, -Me, -Ph, -Ar). Mechanistic and density functional theory studies revealed that the unsaturated propargyl moiety can behave as an electrophile when aromatic terminal substitutions are made, and therefore competes with leaving group substitution for new outcomes. Selected products from the cascade reactions were investigated for their absorption and fluorescence properties, including transient absorption spectroscopy. This revealed polarity dependent excited state relaxation pathways, fluorescence, and triplet formation, thus highlighting these reactions as a means to access diverse functional materials rapidly.
| Item ID: | 80599 |
|---|---|
| Item Type: | Article (Research - C1) |
| ISSN: | 0947-6539 |
| Keywords: | density functional calculations, domino reactions, dyes/pigments, molecular diversity, photophysics |
| Copyright Information: | © 2021 Wiley-VCH GmbH. |
| Date Deposited: | 29 Sep 2023 02:27 |
| FoR Codes: | 34 CHEMICAL SCIENCES > 3405 Organic chemistry > 340503 Organic chemical synthesis @ 65% 34 CHEMICAL SCIENCES > 3405 Organic chemistry > 340505 Physical organic chemistry @ 35% |
| SEO Codes: | 28 EXPANDING KNOWLEDGE > 2801 Expanding knowledge > 280105 Expanding knowledge in the chemical sciences @ 100% |
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