The Cascade Reactions of Indigo with Propargyl Substrates for Heterocyclic and Photophysical Diversity
Mccosker PM, Butler NM, Shakoori A, Volland M, Perry MJ, Mullen JW, Willis AC, Clark T, Bremner JB, Guldi DM, Keller PA (2021)
Publication Type: Journal article
Publication year: 2021
Journal
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.
Authors with CRIS profile
Michel Volland
Lehrstuhl für Physikalische Chemie I
Timothy Clark
Computer-Chemie-Centrum
Dirk Michael Guldi
Lehrstuhl für Physikalische Chemie I
Involved external institutions
Australia (AU)How to cite
APA:
Mccosker, P.M., Butler, N.M., Shakoori, A., Volland, M., Perry, M.J., Mullen, J.W.,... Keller, P.A. (2021). The Cascade Reactions of Indigo with Propargyl Substrates for Heterocyclic and Photophysical Diversity. Chemistry - A European Journal. https://doi.org/10.1002/chem.202003662
MLA:
Mccosker, Patrick M., et al. "The Cascade Reactions of Indigo with Propargyl Substrates for Heterocyclic and Photophysical Diversity." Chemistry - A European Journal (2021).
BibTeX: Download