Enantiopure sulfinyl azobenzenes as chiroptical switches

被引:21
作者
Carreno, MC [1 ]
García, I
Ribagorda, M
Merino, E
Pieraccini, S
Spada, GP
机构
[1] Univ Autonoma Madrid, Dept Quim Organ, E-28049 Madrid, Spain
[2] Univ Bologna, Dipartimento Chim Organ A Mangini, Alma Mater Studiorum, I-40126 Bologna, Italy
关键词
D O I
10.1021/ol050789o
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Photoswitchable enantiopure sulfinyl azo compounds have been synthesized. A remarkable perturbation of the azo system by the stereogenic sulfinyl moiety has been observed by CD in both the trans and the cis azobenzenes resulting by photoisomerization. After five irradiation cycles, the configurational integrity of these chiral switches remains unchanged.
引用
收藏
页码:2869 / 2872
页数:4
相关论文
共 43 条
[11]   Photochromic compounds: Chemistry and application in ophthalmic lenses [J].
Crano, JC ;
Flood, T ;
Knowles, D ;
Kumar, A ;
VanGemert, B .
PURE AND APPLIED CHEMISTRY, 1996, 68 (07) :1395-1398
[12]  
DURR H, 1900, PHOTOCHROMISM MOL SY
[13]   Recent developments in the synthesis and utilization of chiral sulfoxides [J].
Fernández, I ;
Khiar, N .
CHEMICAL REVIEWS, 2003, 103 (09) :3651-3705
[14]  
FERRINGA L, 2001, MOL SWITCHERS, pCH5
[15]   ASSIGNMENT OF SULPHOXIDE CONFIGURATION BY NUCLEAR MAGNETIC RESONANCE METHOD [J].
FOSTER, AB ;
INCH, TD ;
QADIR, MH ;
WEBBER, JM .
CHEMICAL COMMUNICATIONS, 1968, (18) :1086-&
[16]   Synthesis and characterization of two chiral azobenzene-containing copolymers [J].
Iftime, G ;
Natansohn, A ;
Rochon, P .
MACROMOLECULES, 2002, 35 (02) :365-369
[17]   Diarylethenes for memories and switches [J].
Irie, M .
CHEMICAL REVIEWS, 2000, 100 (05) :1685-1716
[18]   Stimuli-responsive polymers. VII. Photomodulated chiroptical switches: Periodic copolyaramides containing azobenzene, phenylene, and chiral binaphthylene main-chain linkages [J].
Jaycox, GD .
JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2004, 42 (03) :566-577
[19]   MODELING CHEMICAL-REACTIVITY .3. STEREOCHEMISTRY OF MICHAEL ADDITIONS OF VINYL SULFOXIDES [J].
KAHN, SD ;
HEHRE, WJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (23) :7399-7400
[20]  
Kelker HC., 1980, Handbook of liquid crystals