Transition-metal-free synthesis and photophysical studies of highly functionalized ()-stilbenes

Metal-free synthesis of highly functionalized ( E )-stilbenes cored with electronic donor and acceptor functionalities was achieved through a carbanion-induced ring transformation reaction between ( E )-4-(4-(dimethylamino)phenyl)but-3-en-2-one 12 and 6-aryl-2 H -pyran-2-ones 9 in the presence of a...

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Bibliographic Details
Published in:New journal of chemistry 2023-12, Vol.48 (1), p.342-35
Main Authors: Mamgain, Ritu, , Malik, Abhrajeet, Singh, Fateh V
Format: Article
Language:English
Subjects:
Synthesis
Thermal stability
Transition metals
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Summary:Metal-free synthesis of highly functionalized ( E )-stilbenes cored with electronic donor and acceptor functionalities was achieved through a carbanion-induced ring transformation reaction between ( E )-4-(4-(dimethylamino)phenyl)but-3-en-2-one 12 and 6-aryl-2 H -pyran-2-ones 9 in the presence of a base. The procedure has several advantages, including mild reaction conditions, readily available precursors, metal-free synthesis, simple setup, and the synthesis of various substituted regioselective ( E )-stilbenes in good yields. All the synthesized compounds 13a-j were found to be thermally stable and exhibited fluorescence in the range of 436-490 nm. A considerable positive solvatochromic behaviour in different solvents of varying polarity was observed, and the concentration study indicated the non-aggregating behaviour of all the synthesized compounds. Functionalized blue florescent ( E )-stilbenes 13 were synthesized by the carbanion-induced ring transformation of α-pyranones 9 with ketones and their photophysical behaviour was studied by using UV-visible and fluorescence spectroscopy.
ISSN:1144-0546
1369-9261
DOI:10.1039/d3nj03458e