A photoactivated 'molecular train' for optoelectronic applications:: light-stimulated translocation of a β-cyclodextrin receptor within a stoppered azobenzone-alkyl chain supramolecular monolayer assembly on a Au-electrode

被引：159

作者：

Willner, I ^{[1
]}

Pardo-Yissar, V ^{[1
]}

Katz, E ^{[1
]}

Ranjit, KT ^{[1
]}

机构：

[1] Hebrew Univ Jerusalem, Inst Chem, IL-91904 Jerusalem, Israel

来源：

JOURNAL OF ELECTROANALYTICAL CHEMISTRY | 2001年 / 497卷 / 1-2期

关键词：

optoelectronics; molecular machine; monolayer; self-assembly; chronoamperometry; photoisomerization;

D O I：

10.1016/S0022-0728(00)00455-1

中图分类号：

O65 [分析化学];

学科分类号：

070302 ; 081704 ;

摘要：

A light-driven molecular shuttle is organized on a gold electrode surface. The assembly consists of a ferrocene-functionalized beta -cyclodextrin, Fc-beta -CD, molecule threaded on a monolayer-immobilized long alkyl component containing a photoisomerizable azobenzene unit, and terminated with a bulky anthracene group. The Fc-beta -CD resides preferentially on the trans-azobenzene component, and photoisomerization of the trans-azobenzene to the cis-azobenzene state causes the translocation of the Fc-beta -CD to the alkyl-chain component of the assembly. The state of the molecular shuttle is electronically transduced by chronoamperometry. The interfacial electron transfer rate constants for the oxidation of the ferrocene units of Fc-beta -CD in the respective positions are k(t) = 65 s(-1) and k(c) = 15 s(-1). The light-driven translocation of Fc-beta -CD is reversible, and proceeds by the cyclic isomerization of the azobenzene component between the trans and cis states. (C) 2001 Elsevier Science B.V. All rights reserved.

引用

页码：172 / 177

页数：6

共 18 条

[1] Application of a nitrospiropyran-FAD-reconstituted glucose oxidase and charged electron mediators as optobioelectronic assemblies for the amperometric transduction of recorded optical signals: Control of the ''on''-''off'' direction of the photoswitch [J].

Blonder, R ;

Katz, E ;

Willner, I ;

Wray, V ;

Buckmann, AF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (49) :11747-11757

[2]

Carter F. L., 1988, Molecular electronic devices, V1st

[3] A MOLECULAR PHOTOIONIC AND GATE BASED ON FLUORESCENT SIGNALING [J].

DE SILVA, AP ;

GUNARATNE, HQN ;

MCCOY, CP .

NATURE, 1993, 364 (6432) :42-44

[4] Photochemically-, chemically-, and pH-controlled electrochemistry at functionalized spiropyran monolayer electrodes [J].

Doron, A ;

Katz, E ;

Tao, GL ;

Willner, I .

LANGMUIR, 1997, 13 (06) :1783-1790

[5] Amperometric transduction and amplification of optical signals recorded by a phenoxynaphthacenequinone monolayer electrode: Photochemical and pH-gated electron transfer [J].

Doron, A ;

Portnoy, M ;

LionDagan, M ;

Katz, E ;

Willner, I .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (37) :8937-8944

[6]

Drexler K. E., 1992, NANOSYSTEMS MOL MACH

[7] pH-switched electrochemistry of pyrroloquinoline quinone at Au electrodes modified by functionalized monolayers [J].

Katz, E ;

LionDagan, M ;

Willner, I .

JOURNAL OF ELECTROANALYTICAL CHEMISTRY, 1996, 408 (1-2) :107-112

[8] Kinetic separation of amperometric responses of composite redox-active monolayers assembled onto Au electrodes: Implications to the monolayers' structure and composition [J].

Katz, E ;

Willner, I .

LANGMUIR, 1997, 13 (13) :3364-3373

[9] A DUAL-MODE MOLECULAR SWITCHING DEVICE - BISPHENOLIC DIARYLETHENES WITH INTEGRATED PHOTOCHROMIC AND ELECTROCHROMIC PROPERTIES [J].

KAWAI, SH ;

GILAT, SL ;

PONSINET, R ;

LEHN, JM .

CHEMISTRY-A EUROPEAN JOURNAL, 1995, 1 (05) :285-293

[10] Peptide-based molecular shuttles [J].

Lane, AS ;

Leigh, DA ;

Murphy, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (45) :11092-11093

← 1 2 →