Stimuli-Responsive Azulene-Based Conjugated Oligomers with Polyaniline-like Properties

被引：160

作者：

Amir, Elizabeth ^{[1
,2
]}

Amir, Roey J. ^{[1
,2
]}

Campos, Luis M. ^{[3
,4
]}

Hawker, Craig J. ^{[1
,2
]}

机构：

[1] Univ Calif Santa Barbara, Dept Mat, Mat Res Lab, Santa Barbara, CA 93106 USA

[2] Univ Calif Santa Barbara, Dept Chem & Biochem, Santa Barbara, CA 93106 USA

[3] Columbia Univ, Dept Chem, New York, NY 10027 USA

[4] Columbia Univ, Energy Frontier Res Ctr, New York, NY 10027 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2011年 / 133卷 / 26期

基金：

美国国家科学基金会;

关键词：

EMISSION; POLYTHIOPHENES; COPOLYMERS; OXIDATION; UNITS;

D O I：

10.1021/ja203267g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Novel azulene building blocks, prepared via the cycloaddition of thiophene-S,S-dioxides and fulvenes, allow for incorporation of the seven-membered ring of the azulene nucleus directly into the backbone of conjugated materials. This unique mode of incorporation gives remarkably stable, stimuli-responsive materials upon exposure to acid. This simple doping/dedoping strategy provides for effective optical band gap control and on/off fluorescence switching, reminiscent of polyaniline.

引用

页码：10046 / 10049

页数：4

共 29 条

[1] Synthesis of [all]-S,S-dioxide oligothiophenes using HOF•CH3CN [J].

Amir, E ;

Rozen, S .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (45) :7374-7378

[2] ANOMALOUS LIGHT EMISSION OF AZULENE [J].

BEER, M ;

LONGUETHIGGINS, HC .

JOURNAL OF CHEMICAL PHYSICS, 1955, 23 (08) :1390-1391

[3] Self-assembly of regioregular, amphiphilic polythiophenes into highly ordered π-stacked conjugated polymer thin films and nanocircuits [J].

Bjornholm, T ;

Greve, DR ;

Reitzel, N ;

Hassenkam, T ;

Kjaer, K ;

Howes, PB ;

Larsen, NB ;

Bogelund, J ;

Jayaraman, M ;

Ewbank, PC ;

McCullough, RD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (30) :7643-7644

[4] Approach to the blues:: A highly flexible route to the azulenes [J].

Carret, S ;

Blanc, A ;

Coquerel, Y ;

Berthod, M ;

Greene, AE ;

Deprés, JP .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (32) :5130-5133

[5] Stille Polycondensation for Synthesis of Functional Materials [J].

Carsten, Bridget ;

He, Feng ;

Son, Hae Jung ;

Xu, Tao ;

Yu, Luping .

CHEMICAL REVIEWS, 2011, 111 (03) :1493-1528

[6] Ring expansion-annulation strategy for the synthesis of substituted azulenes and oligoazulenes. 2. Synthesis of azulenyl halides, sulfonates, and azulenylmetal compounds and their application in transition-metal-mediated coupling reactions [J].

Crombie, AL ;

Kane, JL ;

Shea, KM ;

Danheiser, RL .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (25) :8652-8667

[7]

Frisch M. J., 2016, Gaussian 03 Revision B.03

[8] PROTON DISSOCIATION OF AZULENIUM CATIONS IN EXCITED STATE [J].

GRELLMANN, KH ;

HEILBRONNER, E ;

SEILER, P ;

WELLER, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (16) :4238-+

[9] THE SYNTHESIS AND CHARACTERIZATION OF A SELF-ASSEMBLING AMPHIPHILIC FULLERENE [J].

HAWKER, CJ ;

SAVILLE, PM ;

WHITE, JW .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (12) :3503-3505

[10] Creation of Stabilized Electrochromic Materials by Taking Advantage of Azulene Skeletons [J].

Ito, Shunji ;

Morita, Noboru .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (27) :4567-4579

← 1 2 3 →