Reduced Knoevenagel Reaction of Acetetracenylene-1,2-dione with Acceptor Units for Luminescent Tetracene Derivatives

Yutaka Matsuo, Chu Guo Yu, Takafumi Nakagawa, Hiroshi Okada, Hiroshi Ueno, Tian Ge Sun, Yu Wu Zhong

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

Acetetracenylene-1,2-dione reacted with 3-ethylrhodanine in the presence of piperidine and Hantzsch ester via a Knoevenagel condensation-reduction sequence to give a tetracene-rhodanine adduct. This reduced Knoevenagel product exhibited magenta luminescence with a fluorescence quantum yield of = 0.34 and fluorescence lifetime of = 13.2 ns in toluene. Electrochemical studies and charge carrier transport measurements revealed ambipolar properties with hole and electron mobilities of 5.1 × 10 -7 and 1.6 × 10 -4 cm 2 /(V s), respectively.

Original languageEnglish
JournalJournal of Organic Chemistry
DOIs
Publication statusPublished - 2019 Jan 1
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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