Triflic acid mediated cascade cyclization of aryldiynes for the synthesis of indeno[1,2-c]chromenes: application to dye-sensitized solar cells.
Triflic acid mediated cascade cyclization of aryldiynes for the synthesis of indeno[1,2-c]chromenes: application to dye-sensitized solar cells.
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DOI：
10.1002/chem.201405860
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发表时间：
2015-03
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通讯作者：
Hua Jiang;Giovanni Ferrara;Xuan Zhang;K. Oniwa;A. Islam;Liyuan Han;Ying-Ji Sun;M. Bao;N. Asao;Yoshinori Yamamoto;T. Jin
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作者：
Hua Jiang;Giovanni Ferrara;Xuan Zhang;K. Oniwa;A. Islam;Liyuan Han;Ying-Ji Sun;M. Bao;N. Asao;Yoshinori Yamamoto;T. Jin
报道了一种新的三氟酸(TfOH)催化的邻苯甲醚取代芳基二炔的级联环化反应，用于合成吲哚并[1，2-c]色烯。级联环化反应是通过不寻常的TfOH诱导的炔烃环化和甲氧基对亚甲基阳离子的亲核攻击进行的，这与邻苯胺基或邻硫代苯甲醚取代的芳基二炔的环化反应完全不同。合成了一类以吲哚并[1，2-c]色烯为给电子体和π连接物的新型有机染料。这些化合物在染料敏化太阳能电池(DSCs)中表现出高的光伏性能。
A new triflic acid (TfOH)-mediated cascade cyclization of ortho-anisole-substituted aryldiynes is described for the construction of indeno[1,2-c]chromenes. The cascade cyclization proceeds through an unusual TfOH-induced alkyne-alkyne cyclization followed by nucleophilic attack of the methoxy group on the benzylidene cation, which is completely different to the cyclization of ortho-aniline- or ortho-thioanisole-substituted aryldiynes. A new class of organic dyes with the indeno[1,2-c]chromene framework as both donor and π-linker were synthesized. These compounds exhibit high photovoltaic performances in dye- sensitized solar cells (DSCs).