Synthesis of Anthradan analogues by regioselective FriedelaCrafts reactions on N,N-dihexylanthracen-2-amine

Synthesis of Anthradan analogues by regioselective FriedelaCrafts reactions on N,N-dihexylanthracen-2-amine

An efficient synthetic route using a FriedelaCrafts acylation approach was developed to obtain fluorophores such as 1-(6-(dihexylamino)anthracen-1-yl)propan-1-one (1b) and 1-(7-(dihexylamino)anthracen-1-yl)propan-1-one (1c) with a pushapull electronic conjugation starting from 2-aminoanthracene-9,10...

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Bibliographic Details
Published in:Tetrahedron letters Vol. 54; no. 21; pp. 2587 - 2590
Main Authors: de Miranda, Maicon G, de Oliveira, Matheus FG, Lopes, Rosangela SC, da Silva, Antonio JR, Albert, Andre LM, Lopes, Claudio C
Format: Journal Article
Language:English
Published: 22-05-2013
Subjects:
Chemical compounds
Conjugation
Derivatives
Electronics
Emission
Fluorescence
Red shift
Tetrahedrons
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Summary:An efficient synthetic route using a FriedelaCrafts acylation approach was developed to obtain fluorophores such as 1-(6-(dihexylamino)anthracen-1-yl)propan-1-one (1b) and 1-(7-(dihexylamino)anthracen-1-yl)propan-1-one (1c) with a pushapull electronic conjugation starting from 2-aminoanthracene-9,10-dione (4). These compounds are analogues of 1-(6-(dihexylamino)anthracen-2-yl)propan-1-one (Anthradan) and they exhibit the same additional redshift emission and absorption spectra. Furthermore, we have synthesized other derivatives of Anthradan via the FriedelaCrafts approach in good yields.
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ISSN:0040-4039