Control of photoisomerization of C=C double bond by hydrogen bonding and photoinduced hydrogen atom transfer

被引:9
作者
Azechi, Yousuke [1 ]
Takemura, Keiko [1 ]
Shinohara, Yoshihiro [1 ]
Nishimura, Yoshinobu [1 ]
Arai, Tatsuo [1 ]
机构
[1] Univ Tsukuba, Grad Sch Pure & Appl Sci, Tsukuba, Ibaraki 3058571, Japan
关键词
isomerization; hydrogen atom transfer;
D O I
10.1002/poc.1239
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Olefins with a phenathroline ring and a pyrrole ring were prepared and hydrogen atom transfer reaction in the excited singlet state was observed. The tautomer produced in the excited singlet state has lifetime of 30-50 ps for cis-1 and c,t-2 and with fluorescence maximum at longer wavelength region at 640 nm. The compound 1 exhibited photochromic behavior with its absorption maximum changing between 380 nm and 440 nm, while 2 exhibited only the small change of the absorption spectra on photoirradiation. Copyright (c) 2007 John Wiley & Sons, Ltd.
引用
收藏
页码:864 / 871
页数:8
相关论文
共 22 条
[1]   Effect of formyl group on photoinduced hydrogen atom transfer and cis-trans isomerization of 2[2-(2-pyrrolyl)ethenyl]pyridine [J].
Arai, T ;
Hozumi, Y .
CHEMISTRY LETTERS, 1998, (11) :1153-1154
[2]   Photochemical behavior of 2-[2-(2-pyridyl) ethenyl] indole on triplet sensitization. Spin multiplicity dependence of the isomerization modes of an intramolecularly hydrogen-bonded compound [J].
Arai, T ;
Obi, M ;
Iwasaki, T ;
Tokumaru, K ;
Lewis, FD .
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 1996, 96 (1-3) :65-69
[3]   NOVEL PHOTOINDUCED HYDROGEN-ATOM TRANSFER THROUGH INTRAMOLECULAR HYDROGEN-BONDING COUPLED WITH CIS-TRANS ISOMERIZATION IN CIS-1-(2-PYRROLYL)-2-(2-QUINOLYL)ETHENE [J].
ARAI, T ;
MORIYAMA, M ;
TOKUMARU, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (07) :3171-3172
[4]  
Arai T, 1999, CHEM LETT, P965
[5]   PICOSECOND KINETIC AND VIBRATIONALLY RESOLVED SPECTROSCOPIC STUDIES OF INTRAMOLECULAR EXCITED-STATE HYDROGEN-ATOM TRANSFER [J].
BARBARA, PF ;
WALSH, PK ;
BRUS, LE .
JOURNAL OF PHYSICAL CHEMISTRY, 1989, 93 (01) :29-34
[6]   PICOSECOND SINGLE PHOTON TIMING MEASUREMENTS WITH A PROXIMITY TYPE MICROCHANNEL PLATE PHOTOMULTIPLIER AND GLOBAL ANALYSIS WITH REFERENCE CONVOLUTION [J].
BOENS, N ;
TAMAI, N ;
YAMAZAKI, I ;
YAMAZAKI, T .
PHOTOCHEMISTRY AND PHOTOBIOLOGY, 1990, 52 (04) :911-917
[7]   Intramolecular proton or hydrogen-atom transfer in the ground and excited states of 2-hydroxybenzoyl compounds [J].
Catalan, J ;
Palomar, J ;
dePaz, JLG .
JOURNAL OF PHYSICAL CHEMISTRY A, 1997, 101 (42) :7914-7921
[8]  
FORMOSINHO SJ, 1993, J PHOTOCH PHOTOBIO A, V75, P1
[9]   Photoisomerization and fluorescence properties of hemiindigo compounds having intramolecular hydrogen bonding [J].
Ikegami, M ;
Arai, T .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2003, 76 (09) :1783-1792
[10]   The photoinduced hydrogen atom transfer and trans-cis isomerization of the C=C double bond in 1-(1-hydroxy-2-naphthyl)-3-(1-naphthyl)-2-propen-1-one and related compounds studied using nanosecond time-resolved infrared spectroscopy [J].
Kaneda, K ;
Sato, S ;
Hamaguchi, H ;
Arai, T .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2004, 77 (08) :1529-1535