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Cover Feature: The Cascade Reactions of Indigo with Propargyl Substrates for Heterocyclic and Photophysical Diversity (Chem. Eur. J. 11/2021)
Author(s) -
McCosker Patrick M.,
Butler Nicholas M.,
Shakoori Alireza,
Volland Michel K.,
Perry Matthew J.,
Mullen Jesse W.,
Willis Anthony C.,
Clark Timothy,
Bremner John B.,
Guldi Dirk M.,
Keller Paul A.
Publication year - 2021
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202004188
Subject(s) - propargyl , indigo , chemistry , electrophile , domino , photochemistry , fluorescence , combinatorial chemistry , computational chemistry , organic chemistry , catalysis , art , visual arts , physics , quantum mechanics
One‐pot domino reactions of indigo with propargyl derivatives produce structurally diverse heterocycles including new pyrazinodiindolodiones, azepinodiindolones, and oxazinoindolones. Mechanistic and DFT studies show propargyl moieties behaving as electrophiles when terminally substituted, thereby competing with leaving groups. Photophysical properties, including transient absorption spectroscopy reveal polarity‐dependent excited state relaxation pathways, fluorescence, and triplet formation. More information can be found in the Full Paper by P. A. Keller et al. on page 3708.