Max Planck Institute for Polymer Research, Ackermannweg 10, D-55128, Mainz, Germany.
J Org Chem. 2008 Dec 5;73(23):9207-13. doi: 10.1021/jo801898g.
Ladder-type heteroacenes containing pyrrole and thiophene rings, dibenzo[b,b']thieno[2,3-f:5,4-f']-carbazoles (DBTCZ, 1), and diindolo[3,2-b:2',3'-h]benzo[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 ring 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.
包含吡咯和噻吩环的梯形杂芳烃，二苯并[b,b']噻吩并[2,3-f:5,4-f']咔唑（DBTCZ，1）和二吲哚并[3,2-b:2',3'-h]苯并[1,2-b:4,5-b']双[1]苯并噻吩（DIBBBT，2），分别通过适当的前体（7、11 和 18）简便地合成。关键步骤是相应的芳基甲基砜与活化的芳族构建块在三氟磺酸诱导下进行分子内亲电偶联反应，从而实现区域选择性环闭合。两种前体（7 和 11）都能得到 DBTCZ 的对称产物，但带有不同方式的可溶性烷基链。DIBBBT 也作为具有确定结构的扩展梯形杂芳烃合成。这些得到的杂芳烃都经过了充分的表征（质谱、NMR、元素分析），并报告了它们的 X 射线分析、光学和电化学性质。
