Synthesis of Large Polycyclic Aromatic Hydrocarbons from Bis(biaryl)acetylenes: Large Planar PAHs with Low π-Sextets

被引：48

作者：

Chen, Tse-An ^{[1
]}

Liu, Rai-Shung ^{[1
]}

机构：

[1] Natl Tsing Hua Univ, Dept Chem, Hsinchu 30013, Taiwan

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 17期

关键词：

DISCOTIC LIQUID-CRYSTALS; SCHOLL REACTION; DERIVATIVES; ELECTRONICS; CYCLIZATION; CHEMISTRY; OXIDANT; DDQ;

D O I：

10.1021/ol201854g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new synthesis of large PAHs with low Clar sextets was developed. This synthesis involves initial bis(biaryl)acetylene 1, which undergoes initial ICI-aromatization and a subsequent Mizoroki-Heck coupling reaction to give dibenzochrysene derivative 3 that can be transformed into planar PAHs 4 using DDQ-oxidation.

引用

页码：4644 / 4647

页数：4

共 30 条

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

Anthony, John E. .

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

[2] 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

[3] Current-voltage characteristics of a homologous series of polycyclic aromatic hydrocarbons [J].

Boehme, Thilo ;

Simpson, Christopher D. ;

Muellen, Klaus ;

Rabe, Juergen P. .

CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (26) :7349-7357

[4] Functionalized dibenzo[g,p]chrysenes:: Variable photophysical and electronic properties and liquid-crystal chemistry [J].

Chaudhuri, Rupsha ;

Hsu, Ming-Yu ;

Li, Chia-Wen ;

Wang, Cheng-l ;

Chen, Chun-Jung ;

Lai, Chung K. ;

Chen, Li-Yin ;

Liu, Su-Hao ;

Wu, Chung-Chih ;

Liu, Rai-Shung .

ORGANIC LETTERS, 2008, 10 (14) :3053-3056

[5] Synthesis of Polyaromatic Hydrocarbons from Bis(biaryl)diynes: Large PAHs with Low Clar Sextets [J].

Chen, Tse-An ;

Liu, Rai-Shung .

CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (29) :8023-8027

[6]

CLAR E, 1952, J AM CHEM SOC, V62, P6235

[7]

Clar E., 1972, The Aromatic Sextet

[8]

Clar E., 1964, Polycyclic hydrocarbons, V1, P2

[9] Domino Diels-Alder Cycloadditions of Arynes: New Approach to Elusive Perylene Derivatives [J].

Criado, Alejandro ;

Pena, Diego ;

Cobas, Agustin ;

Guitian, Enrique .

CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (32) :9736-9740

[10] Synthesis of large polycyclic aromatic hydrocarbons:: Variation of size and periphery [J].

Dötz, F ;

Brand, JD ;

Ito, S ;

Gherghel, L ;

Müllen, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (32) :7707-7717

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