Conjugated Ladder-Type Heteroacenes Bearing Pyrrole and Thiophene Ring Units: Facile Synthesis and Characterization

被引：61

作者：

Gao, Peng ^{[1
]}

Feng, Xinliang ^{[1
]}

Yang, Xiaoyin ^{[1
]}

Enkelmann, Volker ^{[1
]}

Baumgarten, Martin ^{[1
]}

Muellen, Klaus ^{[1
]}

机构：

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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 23期

关键词：

D O I：

10.1021/jo801898g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Ladder-type heteroacenes containing pyrrole and thiophene rings, dibenzo [b'b']thieno[2,3-f:5,4-f']-carbazoles (BBTCZ, 1) and diindolo[3,2-b:2'3'-h]benzol[1,2-b:4,5-b']bis[1]benzothiophene (DIBBBT), 2). were facilely synthesized through proper precursors (7, 11, and 18) respectively. The key step is a triflic acid induced intramolecular electrophilic coupling reaction of corresponding aromatic methyl Sulfoxides with activated aromatic building, blocks, which enables regioselective rim, closure. Both precursors (7 and 11) toward DBTCZ gave the symmetrical product but with solubilizing alkyl chains in two different Fashions. DIBBBT was also synthesized as the extended ladder-type heteroacene with defined Structure. These obtained heteroacenes are fully characterized (mass spectrometry, NMR, elemental analysis). and their X-ray analysis and optical and electrochemical properties are reported.

引用

页码：9207 / 9213

页数：7

共 30 条

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