Synthesis and characterization of 2H-pyrano[3,2-c]coumarin derivatives and their photochromic and redox properties

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Title:	Synthesis and characterization of 2H-pyrano[3,2-c]coumarin derivatives and their photochromic and redox properties
Authors:	Huang, C.-N., Kuo, P.-Y., Lin, C.-H., Yang, D.-Y.
Contributors:	Department of Chemistry, Tunghai University
Keywords:	Coumarin;Flindersine;Photochromism;Redox switch
Date:	2007
Issue Date:	2013-05-14T09:03:13Z (UTC)
Abstract:	A series of 2H-pyrano[3,2-c]chromen-5-one derivatives were synthesized and characterized. Their photochromic and redox properties were investigated by the UV-vis absorption spectroscopy. While compounds with one or two phenyl groups incorporated at the 2-position were present in both ring-opened (5a and 10a) and ring-closed (6a and 11a) forms, the incorporation of an N,N-dimethylamino group on either side of the aromatic ring resulted in formation of the ring-opened (5b and 10b) forms only. The ring-closed forms 13 and 18 with a methyl substituent at the 3-position of the pyran moiety failed to exhibit photochromic behavior. Compound 23 with an N,N-dimethylamino group on the aromatic ring displayed increasing shoulder absorption in the visible region and a distinct change of color upon UV irradiation. The non-fluorescent 10b instantly changed from dark red to colorless, when treated with sodium borohydride. The reduced 28 was blue fluorescent with a quantum yield of 0.46 and could be returned to its original color via DDQ oxidation. ? 2007 Elsevier Ltd. All rights reserved.
Relation:	Tetrahedron Volume 63, Issue 40, 1 October 2007, Pages 10025-10033
Appears in Collections:	[Department of Chemistry ] Periodical Articles

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