330157-43-2Relevant articles and documents
Synthesis of new benzocoumaryl oxadiazolyls as strong blue-green fluorescent brighteners
Rajesha,Kiran Kumar,Bhojya Naik,Mahadevan
, p. 88 - 94 (2012/06/18)
The benzocoumarin-3-ethylcarboxylate 2 on treatment with hydrazine hydrate at room temperature afforded benzocoumarin-3-carbohydrazide 3. The compound 3 served as key intermediate in the synthesis of the title compounds. Thus, benzocoumarin-1,3,4-oxadiazolyls 6a-e were obtained in two ways, i.e. one by direct cyclization of benzocoumarin-3-carbohydrazide 3 with substituted benzoic acids in POCl3 and the other by cyclization of Schiff bases of compounds 5a-e in the presence of bromine/acetic acid. The structures of the novel benzocoumaryl oxadiazolyls 6a-e were confirmed by spectral analysis. The benzocoumarin-1,3,4- oxadiazolyls 6a-e exhibited strong blue and green fluorescent properties. The Stoke's shifts range from 43 to 165 nm. The absorption and fluorescence maxima of the benzocoumaryl oxadiazolyls showed good bathochromic shifts.
Intramolecular phototransfer of protons and the quenching of fluorescence of derivatives of 2-(coumarinyl-3)-5-(ortho-hydroxyphenyl)-1,3,4-oxadiazole
Doroshenko,Posokhov,Sytnik,Kovalenko
, p. 633 - 644 (2007/10/03)
The spectral-luminescence properties of ortho-hydroxy derivatives of 2-(coumarinyl-3)-5-phenyl-1,3,4-oxadiazole have been studied. It is shown that the basic reason for the decreased quantum yield of emission for the compounds studied is the high-speed phototransfer of a proton (estimated as ～109 s-1). Fluorescence of the products of this reaction (phototautomers) was not observed. It was confirmed by quantum-chemical calculations that the increase in efficiency of nonradiative dissipation of the electron excitation energy in phototautomeric forms of ortho-hydroxycoumarinyloxadiazoles is explained by an increase in intramolecular donor-acceptor interaction on introduction of the coumarin unit into the molecule. As a result of the high efficiency of nonradiative deactivation of the excited state, the ortho-hydroxyderivatives studied have promise as UV photostabilizers in polymeric materials.
