Influence of methoxy substitution on flavonoid photophysics: A steady state and laser flash photolysis study

被引:20
作者
Christoff, M [1 ]
Toscano, VG [1 ]
Baader, WJ [1 ]
机构
[1] UNIV SAO PAULO,INST QUIM,BR-05599970 SAO PAULO,BRAZIL
基金
巴西圣保罗研究基金会;
关键词
flavonoid photophysics; laser flash photolysis; methoxy substitution; steady state photolysis;
D O I
10.1016/S1010-6030(96)04422-X
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
A comparative study of the photophysical properties of three flavonoids (flavone (F), 7-methoxyflavone (7MF) and 3-methoxyflavone (3MF)), which may serve as models for naturally occurring flavonoids, shows a distinct behaviour of the 3-methoxy derivative. Steady state and transient spectroscopic investigations reveal an almost quantitative formation of the triplet states of F and 7MF, which can be observed as transient absorptions and show electron donor and acceptor properties. In contrast, 3MF shows reduced triplet formation, and the transient observed is identified as a I,4-biradical, formed by intramolecular hydrogen abstraction, which behaves as an electron donor.
引用
收藏
页码:11 / 20
页数:10
相关论文
共 42 条
[1]  
AGRAWAL PK, 1981, HETEROCYCLES, V16, P2181
[2]  
AVILA V, 1995, J CHEM SOC P2, P228
[3]   ELECTROSTATIC PROPERTIES OF ZWITTERIONIC MICELLES [J].
BAPTISTA, MD ;
CUCCOVIA, I ;
CHAIMOVICH, H ;
POLITI, MJ ;
REED, WF .
JOURNAL OF PHYSICAL CHEMISTRY, 1992, 96 (15) :6442-6449
[4]   NANOSECOND TRANSIENT PROCESSES IN THE TRIETHYLAMINE QUENCHING OF BENZOPHENONE TRIPLETS IN AQUEOUS ALKALINE MEDIA - SUBSTITUENT EFFECT, KETYL RADICAL DEPROTONATION, AND SECONDARY PHOTOREDUCTION KINETICS [J].
BHATTACHARYYA, K ;
DAS, PK .
JOURNAL OF PHYSICAL CHEMISTRY, 1986, 90 (17) :3987-3993
[5]   A LASER FLASH-PHOTOLYSIS STUDY OF 2,6-DIMETHYL-3,5-DIPHENYL-4-PYRONE AND RELATED CHROMONES - EVIDENCE FOR TRIPLET-STATE STRUCTURAL RELAXATION FROM QUENCHING BEHAVIORS [J].
BHATTACHARYYA, K ;
RAMAIAH, D ;
DAS, PK ;
GEORGE, MV .
JOURNAL OF PHYSICAL CHEMISTRY, 1986, 90 (22) :5984-5989
[6]   PROTON-TRANSFER AND SOLVENT POLARIZATION DYNAMICS IN 3-HYDROXYFLAVONE [J].
BRUCKER, GA ;
SWINNEY, TC ;
KELLEY, DF .
JOURNAL OF PHYSICAL CHEMISTRY, 1991, 95 (08) :3190-3195
[7]  
Caldwell M.M., 1971, Photophysiology, V6, P131, DOI DOI 10.1016/B978-0-12-282606-1.50010-6
[8]   EXTINCTION COEFFICIENTS OF TRIPLET-TRIPLET ABSORPTION-SPECTRA OF ORGANIC-MOLECULES IN CONDENSED PHASES - A LEAST-SQUARES ANALYSIS [J].
CARMICHAEL, I ;
HELMAN, WP ;
HUG, GL .
JOURNAL OF PHYSICAL AND CHEMICAL REFERENCE DATA, 1987, 16 (02) :239-260
[9]  
CHRISTOFF M, UNPUB
[10]   SOLVENT REORDERING OF LOW LYING TRIPLET STATES IN SOME AROMATIC CARBONYLS [J].
GALLIVAN, JB ;
BRINEN, JS .
CHEMICAL PHYSICS LETTERS, 1971, 10 (04) :455-&