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Versatile Colorant Syntheses by Multiple Condensations of Acetyl Anilines with Perylene Anhydrides
Author(s) -
Jänsch Daniel,
Li Chen,
Chen Long,
Wagner Manfred,
Müllen Klaus
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201409634
Subject(s) - intramolecular force , chemistry , aldol condensation , aniline , malononitrile , perylene , imide , chromophore , surface modification , organic chemistry , combinatorial chemistry , polymer chemistry , molecule , catalysis
We report a key step forward in rylene chemistry: the transformation of rylenes into novel chromophore families. The imidization of rylene anhydrides with 2‐acetyl anilines could be controlled by the choice of the solvent, thus causing a transformation into either a 4‐hydroxyquinoline (4‐HQ) or a 4‐oxoquinoline (4‐OQ) unit. The 4‐OQ motif contains an aminoenone group formed by intramolecular aldol condensation and is the first vinylogous rylene imide. The concept of vinylogy was further developed by utilizing 2,6‐diacetyl aniline leading to an 3a‐aza‐1,6‐phenalenedione‐extended rylene skeleton fully embracing the nitrogen atom. By functionalization of the aminoenone motifs, for example, malononitrile addition at the carbonyl groups, the optical and electronic properties could be further tuned.