A Facile Synthesis of Elusive Alkoxy-Substituted Hexa-peri-hexabenzocoronene

被引：65

作者：

Wadumethrige, Shriya H. ^{[1
]}

Rathore, Rajendra ^{[1
]}

机构：

[1] Marquette Univ, Dept Chem, Milwaukee, WI 53201 USA

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 22期

基金：

美国国家科学基金会;

关键词：

D O I：

10.1021/ol8020429

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Oxidative cyclodehydrogenation of hexakis(4-alkoxyphenyl)benzene produces a quantitative yield of an indenofluorene derivative rather than the expected alkoxy-substituted hexa-peri-hexabenzocoronene (HBC). The structure of the unexpected indenofluorene was established by X-ray crystallography. The mechanistic considerations for the formation of the indenofluorene derivative led us to devise an alternative synthesis of elusive alkoxy-substituted HBC-a potentially important, disk-shaped structure for the preparation of liquid crystalline materials for practical applications in the emerging areas of molecular electronics and nanotechnology.

引用

页码：5139 / 5142

页数：4

共 38 条

[1] A modified in situ Suzuki cross-coupling of haloarenes for the preparation of C-2-symmetric biaryls [J].

Andersen, NG ;

Maddaford, SP ;

Keay, BA .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (26) :9556-9559

[2] Low molar mass and polymer discotics: Structure, dynamics and opto-electronic properties [J].

Bayer, A ;

Zimmermann, S ;

Wendorff, JH .

MOLECULAR CRYSTALS AND LIQUID CRYSTALS, 2003, 396 :1-22

[3] Polyphenylene nanostructures [J].

Berresheim, AJ ;

Müller, M ;

Müllen, K .

CHEMICAL REVIEWS, 1999, 99 (07) :1747-1785

[4] Synthesis and electronic properties of iso-alkyl substituted hexa-peri-hexabenzocoronenes (HBC's) from a versatile new HBC synthon, hexakis(4-acetylphenyl)benzene [J].

Chebny, Vincent J. ;

Gwengo, Chengeto ;

Gardinier, James R. ;

Rathore, Rajendra .

TETRAHEDRON LETTERS, 2008, 49 (33) :4869-4872

[5] Toroidal hopping of a single hole through the circularly-arrayed naphthyl groups in hexanaphthylbenzene cation radical [J].

Chebny, Vincent J. ;

Shukla, Ruchi ;

Rathore, Rajendra .

JOURNAL OF PHYSICAL CHEMISTRY A, 2006, 110 (48) :13003-13006

[6] Unexpected phenyl group rearrangement during an intramolecular Scholl reaction leading to an alkoxy-substituted hexa-peri-hexabenzocoronene [J].

Dou, Xi ;

Yang, Xiaoyin ;

Bodwell, Graham J. ;

Wagner, Manfred ;

Enkelmann, Volker ;

Muellen, Klaus .

ORGANIC LETTERS, 2007, 9 (13) :2485-2488

[7]

Fechtenkötter A, 1999, ANGEW CHEM INT EDIT, V38, P3039, DOI 10.1002/(SICI)1521-3773(19991018)38:20<3039::AID-ANIE3039>3.3.CO

[8]

2-X

[9] Synthesis, helical organization, and fibrous formation of C3 symmetric methoxy-substituted discotic hexa-peri-hexabenzocoronene [J].

Feng, Xinliang ;

Pisula, Wojciech ;

Takase, Masayoshi ;

Dou, Xi ;

Enkelmann, Volker ;

Wagner, Manfred ;

Ding, Ning ;

Muellen, Klaus .

CHEMISTRY OF MATERIALS, 2008, 20 (09) :2872-2874

[10] Hexa-peri-hexabenzocoronenes by efficient oxidative cyclodehydrogenation:: The role of the oligophenylene precursors [J].

Feng, XL ;

Wu, JS ;

Enkelmann, V ;

Mullen, K .

ORGANIC LETTERS, 2006, 8 (06) :1145-1148

← 1 2 3 4 →