Domino Diels-Alder Cycloadditions of Arynes: New Approach to Elusive Perylene Derivatives

被引：56

作者：

Criado, Alejandro ^{[1
]}

Pena, Diego ^{[1
]}

Cobas, Agustin ^{[1
]}

Guitian, Enrique ^{[1
]}

机构：

[1] Univ Santiago de Compostela, Dept Quim Organ, Fac Quim, Santiago De Compostela 15782, Spain

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2010年 / 16卷 / 32期

关键词：

arenes; arynes; cycloaddition; domino reactions; hydrocarbons; ACENES; TANDEM; CYCLOTRIMERIZATION; SEMICONDUCTORS; APPROXIMATION; ANNULATION; CHEMISTRY; HEXACENE; BENZYNE;

D O I：

10.1002/chem.201001057

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Figure Presented) A game of dominos: Domino [4+2]/ [4+2] cycloadditions between 1,8-difurylnaphthalene and arynes provide the corresponding adducts in a highly diastereoselective manner. This new synthetic methodology enables the preparation of elusive perylene derivatives with a remarkable reduced HOMO-LUMO gap, a crucial feature for organic semiconductors. © 2010 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：9736 / 9740

页数：5

共 70 条

[1]

[Anonymous], ANGEW CHEM

[2]

[Anonymous], 2009, Angew. Chem

[3]

Anthony J. E., 2008, ANGEW CHEM, V120, P460

[4] The larger acenes: Versatile organic semiconductors [J].

Anthony, John E. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (03) :452-483

[5] Functionalized acenes and heteroacenes for organic electronics [J].

Anthony, John E. .

CHEMICAL REVIEWS, 2006, 106 (12) :5028-5048

[6] MOLECULAR BELTS .2. SUBSTRATE-DIRECTED SYNTHESES OF BELT-TYPE AND CAGE-TYPE STRUCTURES [J].

ASHTON, PR ;

GIRRESER, U ;

GIUFFRIDA, D ;

KOHNKE, FH ;

MATHIAS, JP ;

RAYMO, FM ;

SLAWIN, AMZ ;

STODDART, JF ;

WILLIAMS, DJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (13) :5422-5429

[7] Treatment of electronic excitations within the adiabatic approximation of time dependent density functional theory [J].

Bauernschmitt, R ;

Ahlrichs, R .

CHEMICAL PHYSICS LETTERS, 1996, 256 (4-5) :454-464

[8] Tetrathiafulvalenes, oligoacenenes, and their buckminsterfullerene derivatives: The brick and mortar of organic electronics [J].

Bendikov, M ;

Wudl, F ;

Perepichka, DF .

CHEMICAL REVIEWS, 2004, 104 (11) :4891-4945

[9]

Berlman I. B., 1971, HDB FLUORESCENCE SPE

[10]

Cant A. A., 2009, ANGEW CHEM, V121, P5301

← 1 2 3 4 5 6 7 →