Adding Four Extra K-Regions to Hexa-peri-hexabenzocoronene

被引：48

作者：

Dumslaff, Tim ^{[1
]}

Yang, Bo ^{[1
]}

Maghsoumi, Ali ^{[2
]}

Velpula, Gangamallaiah ^{[3
]}

Mali, Kunal S. ^{[3
]}

Castiglioni, Chiara ^{[3
]}

De Feyter, Steven ^{[3
]}

Tommasini, Matteo ^{[2
]}

Narita, Akimitsu ^{[1
]}

Feng, Xinliang ^{[4
,5
]}

Muellen, Klaus ^{[1
]}

机构：

[1] Max Planck Inst Polymer Res, Ackermannweg 10, D-55128 Mainz, Germany

[2] Politecn Milan, Dipartimento Chim Mat & Ingn Chim G Natta, Piazza Leonardo da Vinci 32, I-20133 Milan, Italy

[3] Univ Leuven, KU Leuven, Dept Chem, Div Mol Imaging & Photon, Celestijnenlaan 200 F, B-3001 Heverlee, Belgium

[4] Tech Univ Dresden, Ctr Adv Elect Dresden, D-01062 Dresden, Germany

[5] Tech Univ Dresden, Dept Chem & Food Chem, D-01062 Dresden, Germany

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2016年 / 138卷 / 14期

基金：

欧洲研究理事会;

关键词：

POLYCYCLIC AROMATIC-HYDROCARBONS; MOLECULES;

D O I：

10.1021/jacs.6b01976

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A multistep synthesis of hexa-peri-hexabenzocoronene (HBC) with four additional K-regions was developed through a precursor based on two benzotetraphene units bridged with p-phenylene, featuring preinstalled zigzag moieties. Characterization by laser desorption/ionization time-of-flight mass spectrometry, Raman and IR spectroscopy, and scanning tunneling microscopy unambiguously validated the successful formation of this novel zigzag edge-rich HBC derivative. STM imaging of its monolayers revealed large-area, defect free adlayers. The optical properties of the modified HBC were investigated by UV/visible absorption spectroscopy.

引用

页码：4726 / 4729

页数：4

共 28 条

[1] Sensor Arrays Based on Polycyclic Aromatic Hydrocarbons: Chemiresistors versus Quartz-Crystal Microbalance [J].

Bachar, Nadav ;

Liberman, Lucy ;

Muallem, Fairouz ;

Feng, Xinliang ;

Muellen, Klaus ;

Haick, Hossam .

ACS APPLIED MATERIALS & INTERFACES, 2013, 5 (22) :11641-11653

[2]

Clar E., 1972, The Aromatic Sextet

[3]

Clar E., 1964, POLYCYCLIC HYDROCARB

[4] Synthesis and Controlled Self-Assembly of Covalently Linked Hexa-peri-hexabenzocoronene/Perylene Diimide Dyads as Models To Study Fundamental Energy and Electron Transfer Processes [J].

Doessel, Lukas F. ;

Kamm, Valentin ;

Howard, Ian A. ;

Laquai, Frederic ;

Pisula, Wojciech ;

Feng, Xinliang ;

Li, Chen ;

Takase, Masayoshi ;

Kudernac, Tibor ;

De Feyter, Steven ;

Muellen, Klaus .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (13) :5876-5886

[5] Triangle-shaped polycyclic aromatic hydrocarbons [J].

Feng, Xinliang ;

Wu, Jishan ;

Ai, Min ;

Pisula, Wojciech ;

Zhi, Linjie ;

Rabe, Juergen P. ;

Muellen, Klaus .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (17) :3033-3036

[6] Synthesis of ethynyl-substituted quinquephenyls and conversion to extended fused-ring structures [J].

Goldfinger, MB ;

Crawford, KB ;

Swager, TM .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (05) :1676-1686

[7] Directed electrophilic cyclizations: Efficient methodology for the synthesis of fused polycyclic aromatics [J].

Goldfinger, MB ;

Crawford, KB ;

Swager, TM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (20) :4578-4593

[8] Bishexa-peri-hexabenzocoronenyl:: A "superbiphenyl'' [J].

Ito, S ;

Herwig, PT ;

Böhme, T ;

Rabe, JP ;

Rettig, W ;

Müllen, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (32) :7698-7706

[9] Synthesis of electron-poor hexa-peri-hexabenzocoronenes [J].

Jones, David J. ;

Purushothaman, Balaji ;

Ji, Shaomin ;

Holmes, Andrew B. ;

Wong, Wallace W. H. .

CHEMICAL COMMUNICATIONS, 2012, 48 (65) :8066-8068

[10] Conformational identification of individual adsorbed molecules with the STM [J].

Jung, TA ;

Schlittler, RR ;

Gimzewski, JK .

NATURE, 1997, 386 (6626) :696-698

← 1 2 3 →