Triflic acid mediated cascade cyclization of aryldiynes for the synthesis of indeno[1,2-c]chromenes: Application to dye-sensitized solar cells

Hua Jiang, Giovanni Ferrara, Xuan Zhang, Kazuaki Oniwa, Ashraful Islam, Liyuan Han, Ying Ji Sun, Ming Bao, Naoki Asao, Yoshinori Yamamoto, Tienan Jin

Research output: Contribution to journalArticlepeer-review

26 Citations (Scopus)

Abstract

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 dyesensitized solar cells (DSCs).

Original languageEnglish
Pages (from-to)4065-4070
Number of pages6
JournalChemistry - A European Journal
Volume21
Issue number10
DOIs
Publication statusPublished - 2014 Oct 7

Keywords

  • Aryldiynes
  • Cyclization
  • Domino reactions
  • Indeno[1,2-c]chromenes
  • Organic dyes
  • Triflic acid

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Fingerprint

Dive into the research topics of 'Triflic acid mediated cascade cyclization of aryldiynes for the synthesis of indeno[1,2-c]chromenes: Application to dye-sensitized solar cells'. Together they form a unique fingerprint.

Cite this