Chemistry, photophysics, and ultrafast kinetics of two structurally related Schiff bases containing the naphthalene or quinoline ring

被引:66
作者
Fita, P.
Luzina, E.
Dziembowska, T.
Radzewicz, Cz.
Grabowska, A.
机构
[1] Univ Warsaw, Inst Expt Phys, PL-00681 Warsaw, Poland
[2] Polish Acad Sci, Inst Phys Chem, PL-01224 Warsaw, Poland
[3] Tech Univ Szczecin, Inst Fundamental Chem, PL-71065 Szczecin, Poland
关键词
D O I
10.1063/1.2371058
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
The two structurally related Schiff bases, 2-hydroxynaphthylidene-(8-aminoquinoline) (HNAQ) and 2-hydroxynaphthylidene-1'-naphthylamine (HNAN), were studied by means of steady-state and time resolved optical spectroscopies as well as time-dependent density functional theory (TDDFT) calculations. The first one, HNAQ, is stable as a keto tautomer in the ground state and in the excited state in solutions, therefore it was used as a model of a keto tautomer of HNAN which exists mainly in its enol form in the ground state at room temperature. Excited state intramolecular proton transfer in the HNAN molecule leads to a very weak (quantum yield of the order of 10(-4)) strongly Stokes-shifted fluorescence. The characteristic time of the proton transfer (about 30 fs) was estimated from femtosecond transient absorption data supported by global analysis and deconvolution techniques. Approximately 35% of excited molecules create a photochromic form whose lifetime was beyond the time window of the experiment (2 ns). The remaining ones reach the relaxed S-1 state (of a lifetime of approximately 4 ps), whose emission is present in the decay associated difference spectra. Some evidence for the back proton transfer from the ground state of the keto form with the characteristic time of approximately 13 ps was also found. The energies and orbital characteristics of main electronic transitions in both molecules calculated by TDDFT method are also discussed. (c) 2006 American Institute of Physics.
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页数:11
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共 41 条
[1]  
Abbas KA, 1996, CAN J APPL SPECTROSC, V41, P119
[2]   Solid-state electronic absorption, fluorescence and C-13 CPMAS NMR spectroscopic study of thermo- and photo-chromic aromatic Schiff bases [J].
Alarcon, SH ;
Olivieri, AC ;
Nordon, A ;
Harris, RK .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1996, (11) :2293-2296
[3]   Substituent and solvent effects on the proton transfer equilibrium in anils and azo derivatives of naphthol.: Multinuclear NMR study and theoretical calculations [J].
Alarcón, SH ;
Olivieri, AC ;
Sanz, D ;
Claramunt, RM ;
Elguero, J .
JOURNAL OF MOLECULAR STRUCTURE, 2004, 705 (1-3) :1-9
[4]   C-13 NMR SPECTROSCOPIC AND AM1 STUDY OF THE INTRAMOLECULAR PROTON-TRANSFER IN ANILS OF SALICYLALDEHYDE AND 2-HYDROXYNAPHTHALENE-1-CARBALDEHYDE [J].
ALARCON, SH ;
OLIVIERI, AC ;
GONZALEZSIERRA, M .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1994, (05) :1067-1070
[5]  
ALDOSHIN SM, 2004, INT C HYDR BOND MOS, pL12
[6]  
ALDOSHIN SM, 1984, PROBLEMY KRISTALOKHI, P35
[7]  
Antonov L, 2000, J CHEM SOC PERK T 2, V6, P1173
[8]   PHOTOCHEMICAL KINETICS OF SALICYLIDENANILINE [J].
BARBARA, PF ;
RENTZEPIS, PM ;
BRUS, LE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (08) :2786-2791
[9]  
DEMTROEDER W, 1981, LASER SPECTROSCOPY B
[10]   SPECTROSCOPIC STUDIES OF KETO-ENOL EQUILIBRIA .13. N-15-SUBSTITUTED IMINES [J].
DUDEK, G ;
DUDEK, EP .
JOURNAL OF THE CHEMICAL SOCIETY B-PHYSICAL ORGANIC, 1971, (07) :1356-&