Benzoid-quinoid tautomerism of azomethines and their structural analogs: LIV. Dibenzo(benzo)-18-crown-6-containing Imines of 5-hydroxy-2,3-tetramethylene- and 5-Hydroxy-2,3-diphenylbenzo[b]furan-4-carbaldehydes
Dibenzo(benzo)-18-crown-6-containing N-arylimines of 5-hydroxy-2,3-tetramethylene- and 5-hydroxy-2,3-diphenylbenzo[b]-furan-4-carbaldehydes were synthesized and their spectral luminescence properties were investigated. In solutions of 6-bromo- and 6-nitro-substituted compounds a tautomeric equilibrium exists between the benzoid and quinoid forms. In the course of complexing of crown-ether-imines of 5-hydroxy-6-nitro-2,3-diphenylbenzo[b]furan-4-carbaldehyde and 5-hydroxy-6-nitro-2,3-tetramethylenebenzo[b]furan-4-carbaldehyde with cations of alkali and alkaline earth metals the content of the quinoid form was found to decrease. This phenomenon was accompanied by essential changes in the absorption and fluorescence spectra characteristic of chemosensor systems with an intramolecular charge transfer (ICT).
KeywordsTetramethylene Intramolecular Charge Transfer Carbaldehyde Spectral Luminescence Property Quinoid Form
Unable to display preview. Download preview PDF.
- 1.Shepelenko, E.N., Tsukanov, A.V., Revinskii, Yu.V., Dubonosov, A.D., Bren’, V.A., and Minkin, V.I., Zh. Org. Khim., 2007, vol. 43, p. 561.Google Scholar
- 2.Minkin, V.I., Gribanova, T.N., Dubonosov, A.D., Bren’, V.A., Minyaev, R.M., Shepelenko, E.N., Tsukanov, A.V., Ros. Khim. Zh., 2004, vol. 48, p. 30.Google Scholar
- 3.Tsivadze, A.Yu., Varnek, A.A., and Khutorskii, V.E., Koordinatsionnye soedineniya metallov s kraunligandami (Coordination Compounds of Metals with Crown-Ethers), Moscow: Nauka, 1991, 397 p.Google Scholar
- 5.Rybalkin, V.P., Bushkov, A.Ya., Bren’, V.A., and Minkin, V.I., Zh. Org. Khim., 1986, vol. 22, p. 565.Google Scholar
- 6.Rybalkin, V.P., Shepelenko, E.N., Popova, L.L., Dubonosov, A.D., Bren’, V.A., and Minkin, V.I., Zh. Org. Khim., 1996, vol. 32, p. 101.Google Scholar
- 9.Knyazhanskii, M.I. and Metelitsa, A.V., Fotoinitsiirovannye protsessy v molekulakh azometinov i ikh strukturnykh analogov (Photoinitiated Processes in Azomethine Molecules and in Their Structural Analogs), Rostov-na-Donu: Izd. RGU, 1992, 208 p.Google Scholar