Chiral discrimination in photochromic helicenes

被引：182

作者：

Wigglesworth, TJ ^{[1
]}

Sud, D ^{[1
]}

Norsten, TB ^{[1
]}

Lekhi, VS ^{[1
]}

Branda, NR ^{[1
]}

机构：

[1] Simon Fraser Univ, Dept Chem, Burnaby, BC V5A 1S6, Canada

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2005年 / 127卷 / 20期

关键词：

D O I：

10.1021/ja050190j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A photoresponsive dithienylethene derivative bearing chiral pinene-based arms underwent a stereoselective photoinduced cyclization reaction to produce greater than 98% of a single diastereomer. The magnitude of the optical rotation changed as much as Δ[α]373 = 8698° upon alternate irradiation with 400 nm and greater than 434 nm light. Copyright © 2005 American Chemical Society.

引用

页码：7272 / 7273

页数：2

共 30 条

[1] Beer G, 2000, ANGEW CHEM INT EDIT, V39, P3252, DOI 10.1002/1521-3773(20000915)39:18<3252::AID-ANIE3252>3.3.CO
[2] 2-G
[3] Berova N., 2000, CIRCULAR DICHROISM P
[4] Photochemical synthesis and optical properties of high membered thiohelicenes
Caronna, T
Sinisi, R
Catellani, M
Luzzati, S
Abbate, S
Longhi, G
[J]. SYNTHETIC METALS, 2001, 119 (1-3) : 79 - 80
[5] Reversible optical transcription of supramolecular chirality into molecular chirality
de Jong, JJD
Lucas, LN
Kellogg, RM
van Esch, JH
Feringa, BL
[J]. SCIENCE, 2004, 304 (5668) : 278 - 281
[6] Feringa B.L., 2001, Molecular Switches
[7] Electron-induced switching of the supramolecular chirality of optically active polythiophene aggregates
Goto, H
Yashima, E
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (27) : 7943 - 7949
[8] OPTICAL PROPERTIES OF SOME HETEROHELICENES - ABSOLUTE CONFIGURATION
GROEN, MB
WYNBERG, H
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (12) : 2968 - &
[9] Electrochiroptical response of 2,2′-(2,2-diarylethenyl)binaphthyl-type electron donors that undergo reversible C-C bond formation/breaking upon two-electron transfer
Higuchi, H
Ohta, E
Kawai, H
Fujiwara, K
Tsuji, T
Suzuki, T
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (17) : 6605 - 6610
[10] Dynamic control and amplification of molecular chirality by circular polarized light
Huck, NPM
Jager, WF
deLange, B
Feringa, BL
[J]. SCIENCE, 1996, 273 (5282) : 1686 - 1688

← 1 2 3 →