Efficient synthesis of a novel, twisted and stable, electroluminescent "Twistacene"

被引：182

作者：

Duong, HM ^{[1
]}

Bendikov, M ^{[1
]}

Steiger, D ^{[1
]}

Zhang, QC ^{[1
]}

Sonmez, G ^{[1
]}

Yamada, J ^{[1
]}

Wudl, F ^{[1
]}

机构：

[1] Univ Calif Los Angeles, Dept Chem & Biochem, Exot Mat Inst, Los Angeles, CA 90095 USA

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 23期

关键词：

D O I：

10.1021/ol035751v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A twistacene, 6,8,15,17-tetraphenyl-1.18,4.5,9.10,13.14-tetrabenzoheptacene (3), was synthesized using a mild and novel bisbenzyne precursor. It was characterized by X-ray crystallography, NMR, UV-vis, and IR spectroscopies, as well as cyclic voltammetry and DFT calculations. The heptacene derivative possesses a nonpropeller twist topology and is unusually stable for a highly conjugated oligoacene. In addition, it is fluorescent, with a quantum efficiency of 15%. Distortion from planarity, mostly due to the phenyl substituents, causes only marginal changes in electronic properties and is beneficial for redox reversibility, which is required for efficient OLED devices.

引用

页码：4433 / 4436

页数：4

共 24 条

[1]

[Anonymous], 1986, THESIS U CALIFORNIA

[2]

[Anonymous], ELECT MAT OLIGOMER A

[3] DIELS-ALDER REACTIVITY OF POLYCYCLIC AROMATIC-HYDROCARBONS .1. ACENES AND BENZOLOGS [J].

BIERMANN, D ;

SCHMIDT, W .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (09) :3163-3173

[4]

BOCK H, 1995, Z NATURFORSCH B, V50, P595

[5]

Clar E., 1964, POLYCYCLIC HYDROCARB, VI

[6]

CLAR E, 1964, POLYCYCLIC HYDROCARB, V2, P200

[7] Organic thin-film transistors: A review of recent advances [J].

Dimitrakopoulos, CD ;

Mascaro, DJ .

IBM JOURNAL OF RESEARCH AND DEVELOPMENT, 2001, 45 (01) :11-27

[8]

Dimitrakopoulos CD, 2002, ADV MATER, V14, P99, DOI 10.1002/1521-4095(20020116)14:2<99::AID-ADMA99>3.0.CO

[9]

2-9

[10] TETRABENZO[DE,NO,ST,C1D1]HEPTACENE [J].

FERGUSON, G ;

PARVEZ, M .

ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE, 1979, 35 (OCT) :2419-2421

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