Dynamic NMR studies of a potential chiroptical switch based on dithiocarbamate-iminodithiolane interconversion

被引：13

作者：

Aubin, LB

Wagner, TM

Thoburn, JD ^{[1
]}

Kesler, BS

Hutchison, KA

Schumaker, RR

Parakka, JP

机构：

[1] Santa Clara Univ, Dept Chem, Santa Clara, CA 95053 USA

[2] San Jose State Univ, Dept Chem, San Jose, CA 95192 USA

[3] Calif Mol Elect Corp, San Jose, CA 95110 USA

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 21期

关键词：

D O I：

10.1021/ol016671z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Variable temperature NMR spectra of the chiral spiro[(4-N,N-dimethyldithiocarbamato)-(2-N,N-dimethylimino)-1,3-dithiolane-5,9'-xanthene] show complex dynamics including degenerate interconversion of the dithiocarbamate and iminodithiolane groups. The rate of this switching process can be controlled by chemical modification: the analogous spiro[dithiolane-fluorene] derivative shows no interconversion. These novel materials have potential application as molecular switching elements in information storage devices.

引用

收藏

页码：3413 / 3416

页数：4

相关论文

共 13 条

[1] A UNIFIED THEORY OF EXCHANGE EFFECTS ON NUCLEAR MAGNETIC RESONANCE LINE SHAPES [J].

BINSCH, G .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (06) :1304-&

[2] DERIVATIVES OF HYDRAZINE .12. ROTATIONAL-ISOMERISM OF METHYL DITHIOCARBAMATES AND DITHIOCARBAZATES [J].

DAHL, BM ;

NIELSEN, H .

ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1974, B 28 (09) :1091-1095

[3] Chiroptical molecular switches [J].

Feringa, BL ;

van Delden, RA ;

Koumura, N ;

Geertsema, EM .

CHEMICAL REVIEWS, 2000, 100 (05) :1789-1816

[4] ROTATIONAL BARRIER IN DITHIOCARBAMATE ESTERS [J].

HOLLOWAY, CE ;

GITLITZ, MH .

CANADIAN JOURNAL OF CHEMISTRY, 1967, 45 (22) :2659-&

[5] Chiropticenes: Molecular chiroptical dipole switches for optical data storage [J].

Hutchison, KA ;

Parakka, JP ;

Kesler, BS ;

Schumaker, RR .

MICRO- AND NANO-PHOTONIC MATERIALS AND DEVICES, 2000, 3937 :64-72

[6] Photochromism: Memories and switches - Introduction [J].

Irie, M .

CHEMICAL REVIEWS, 2000, 100 (05) :1683-1683

[7]

Irie M., 1994, Photoreactive Materials for Ultrahigh-Density Optical Memory

[8] DITHIOCARBAMATES .2. THE FORMATION OF 1,3-DITHIANE, 1,3-DITHIOLANE, AND 1,3-DITHIEPANE QUATERNARY SALTS [J].

KENNARD, KC ;

VANALLAN, JA .

JOURNAL OF ORGANIC CHEMISTRY, 1959, 24 (04) :470-473

[9] DITHIOCARBAMATES IN ORGANIC SYNTHESIS .1. NEW REAGENT FOR ALDEHYDE SYNTHESIS - METHYLENEBIS(N,N-DIMETHYLDITHIOCARBAMATE) [J].

NAKAI, T ;

OKAWARA, M .

CHEMISTRY LETTERS, 1974, (07) :731-732

[10] Molecular-based chiroptical dipole switches [J].

Parakka, JP ;

Schumaker, RR ;

Kesler, BS ;

Thoburn, JD .

OPTICAL ENGINEERING FOR SENSING AND NANOTECHNOLOGY (ICOSN 2001), 2001, 4416 :301-304