Tautomerization in fluorescent states of bipyridyl-diols: A direct confirmation of the intramolecular double proton transfer by electro-optical emission measurements
作者： Paweł Borowicz , Anna Grabowska , Rüdiger Wortmann , Wolfgang Liptay
DOI: 10.1016/0022-2313(92)90029-9
关键词:
摘要: Abstract Integral electro-optical emission measurements (IEOEM) and INDO/S calculations were carried out for 2,2′-bipyridyl- 3,3′-diol (BP(OH)2), its 5-methyl- (MeBP(OH)2) 5,5′-dimethyl- (Me2BP(OH)2) derivatives. All three molecules reported earlier as effective lasing dyes [5,6] undergoing photoautomerization in the S1 state. From IEOEM experiment an upper limit of about 1.0 D (debye) is derived fluorescent state dipole moment, μe, each case, while predict μe excited singlet (π, π∗) diketo monoketo forms range: 0.0–0.5 4.0–4.9 D, respectively. Comparison both results leads to unequivocal discrimination between two possible photoreactions, single or double proton transfer (SPT DPT), shows that species are tautomers produced by DPT.
harvard.edu
elsevier.com
sci-hub.se 参考文章(20)
Hanna Bulska, Anna Grabowska, Zbigniew R. Grabowski, Single and double proton transfer in excited hydroxy derivatives of bipyridyl Journal of Luminescence. ,vol. 35, pp. 189- 197 ,(1986) , 10.1016/0022-2313(86)90010-4
Ł. Kaczmarek, B. Nowak, J. Z̊ukowski, P. Borowicz, J. Sepiol, A. Grabowska, New proton transfer lasing systems—derivatives of 2,2′-bipyridyl. Synthesis and photophysical characteristics Journal of Molecular Structure. ,vol. 248, pp. 189- 200 ,(1991) , 10.1016/0022-2860(91)85013-S
Michael J. S. Dewar, Walter Thiel, Ground states of molecules. 38. The MNDO method. Approximations and parameters Journal of the American Chemical Society. ,vol. 99, pp. 4899- 4907 ,(1977) , 10.1021/JA00457A004
Anna Grabowska, Andrzej Mordzinski, Naoto Tamai, Keitaro Yoshihara, Reversible intramolecular proton-transfer reactions of electronically excited “double” benzoxazoles: A direct observation of the effect of the intrinsic barrier Chemical Physics Letters. ,vol. 169, pp. 450- 456 ,(1990) , 10.1016/0009-2614(90)87076-4
L. H. Vogt, J. G. Wirth, Crystal and molecular structure of 2,2'-bis(6-methyl-3-pyridinol) Journal of the American Chemical Society. ,vol. 93, pp. 5402- 5405 ,(1971) , 10.1021/JA00750A015
Noboru Mataga, Yozo Kaifu, Masao Koizumi, Solvent Effects upon Fluorescence Spectra and the Dipolemoments of Excited Molecules Bulletin of the Chemical Society of Japan. ,vol. 29, pp. 465- 470 ,(1956) , 10.1246/BCSJ.29.465
Jerzy Sepioł, Hanna Bulska, Anna Grabowska, The dihydroxy derivative of 2,2'-bipyridyl as a new proton-transfer lasing dye Chemical Physics Letters. ,vol. 140, pp. 607- 610 ,(1987) , 10.1016/0009-2614(87)80496-7
Jan Jasny, Multifunctional spectrofluorimetric system Journal of Luminescence. ,vol. 17, pp. 149- 173 ,(1978) , 10.1016/0022-2313(78)90082-0
Joan E. Ridley, Michael C. Zerner, Triplet states via intermediate neglect of differential overlap: Benzene, pyridine and the diazines Theoretical Chemistry Accounts. ,vol. 42, pp. 223- 236 ,(1976) , 10.1007/BF00574445
Michael J. S. Dewar, Walter Thiel, Ground states of molecules. 39. MNDO results for molecules containing hydrogen, carbon, nitrogen, and oxygen Journal of the American Chemical Society. ,vol. 99, pp. 4907- 4917 ,(1977) , 10.1021/JA00457A005