Abstract
Quenching of the triplet state of 7,7,9-trimethyl-6,7-dihydrofuro[3,2-f]quinoline (FDHQ) by thymidine 5’-monophosphate disodium salt (TMP) has been observed in the water-alcohol solution with a bimolecular rate constant close in value to the diffusion-limited constant (2.2 × 109 L mol−1 s−1). The products of the steady-state photolysis of a FDHQ-TMP mixture in the water-alcohol solution have been isolated by HPLC and identified by mass spectrometry. Four isomers with a molecular weight of 580 Da equal to the sum of the molecular weights of FDHQ + TMP and with identical mass spectra are the major products of the photolysis. The fragmentation of the molecular ion for all the isomers gives an ion with a weight of 340 Da, indicating the cleavage of the saccharide residue and the formation of the rigid cyclobutane cycle as a result of interaction between the double bond of the nitrogen- or oxygen-containing heterocycle of FDHQ in the triplet state and the C(5)=C(6) double bond of TMP. Diadducts have not been found in the photolysis products. Possible structures of the isomeric products of interaction of FDHQ with TMP have been considered.
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Original Russian Text © O.N. Lygo, T.D. Nekipelova, E.N. Khodot, V.V. Shakhmatov, A.S. Kononikhin, E.N. Nikolaev, V.A. Kuzmin, 2012, published in Khimiya Vysokikh Energii, 2012, Vol. 46, No. 6, pp. 452–457.
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Lygo, O.N., Nekipelova, T.D., Khodot, E.N. et al. Photocycloaddition reaction between 7,7,9-trimethyl-6,7-dihydrofuro[3,2-f]quinoline and thymidine 5′-monophosphate. High Energy Chem 46, 358–362 (2012). https://doi.org/10.1134/S0018143912060069
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DOI: https://doi.org/10.1134/S0018143912060069