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
[11]   LIFETIMES AND ENERGIES OF THE RELAXED TRIPLET-STATES OF CYCLOPENTADIENE AND TETRAMETHYLBUTADIENE - A PULSE-RADIOLYSIS AND PULSED LASER STUDY [J].
GORMAN, AA ;
GOULD, IR ;
HAMBLETT, I .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (15) :4553-4558
[12]   INTERSYSTEM CROSSING AND LOWEST TRIPLET-STATES OF 4-CHROMANONE, CHROMONE, AND FLAVONE [J].
HAMANOUE, K ;
NAKAYAMA, T ;
MIYAKE, T ;
TERANISHI, H .
CHEMISTRY LETTERS, 1981, (01) :39-42
[13]  
HARBORNE JB, 1987, PLANT PIGMENTS
[14]   TRANSIENT ABSORPTION STUDY OF THE INTRAMOLECULAR EXCITED-STATE AND GROUND-STATE PROTON-TRANSFER IN 3-HYDROXYFLAVONE AND 3-HYDROXYCHROMONE [J].
ITOH, M ;
TANIMOTO, Y ;
TOKUMURA, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (10) :3339-3340
[15]   MECHANISM OF INTRAMOLECULAR EXCITED-STATE PROTON-TRANSFER AND RELAXATION PROCESSES IN THE GROUND AND EXCITED-STATES OF 3-HYDROXYFLAVONE AND RELATED-COMPOUNDS [J].
ITOH, M ;
FUJIWARA, Y ;
SUMITANI, M ;
YOSHIHARA, K .
JOURNAL OF PHYSICAL CHEMISTRY, 1986, 90 (22) :5672-5678
[16]   TIME-RESOLVED STUDIES OF BIRADICAL REACTIONS IN SOLUTION [J].
JOHNSTON, LJ ;
SCAIANO, JC .
CHEMICAL REVIEWS, 1989, 89 (03) :521-547
[17]  
Jurd L, 1962, CHEM FLAVONOID COMPO
[18]   STABLE FREE RADICALS .2. REDUCTION OF 1-METHYL-4-CYANOPYRIDINIUM ION TO METHYLVIOLOGEN CATION RADICAL [J].
KOSOWER, EM ;
COTTER, JL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (24) :5524-&
[19]   MOLECULAR PHOTOCHEMISTRY .18. TYPE-2 PHOTOELIMINATION AND 3-OXETANOL FORMATION FROM ALPHA-ALKOXYACETOPHENONES AND RELATED COMPOUNDS [J].
LEWIS, FD ;
TURRO, NJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (02) :311-&
[20]   EFFECTS OF SOLVENT AND SUBSTITUENTS ON ABSORPTION-SPECTRA OF TRIPLET ACETOPHENONE AND ACETOPHENONE KETYL RADICAL STUDIED BY NANOSECOND LASER PHOTOLYSIS [J].
LUTZ, H ;
BREHERET, E ;
LINDQVIS.L .
JOURNAL OF PHYSICAL CHEMISTRY, 1973, 77 (14) :1758-1762