Papers

Peer-reviewed
Feb, 2019

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

The Journal of Organic Chemistry
  • Yutaka Matsuo
  • ,
  • Chu-Guo Yu
  • ,
  • Takafumi Nakagawa
  • ,
  • Hiroshi Okada
  • ,
  • Hiroshi Ueno
  • ,
  • Tian-Ge Sun
  • ,
  • Yu-Wu Zhong

Language
Publishing type
Research paper (scientific journal)
DOI
10.1021/acs.joc.8b03083
Publisher
American Chemical Society ({ACS})

© 2019 American Chemical Society. 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.

Link information
DOI
https://doi.org/10.1021/acs.joc.8b03083
PubMed
https://www.ncbi.nlm.nih.gov/pubmed/30656930
URL
http://orcid.org/0000-0001-9084-9670
Scopus
https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=85061232545&origin=inward
Scopus Citedby
https://www.scopus.com/inward/citedby.uri?partnerID=HzOxMe3b&scp=85061232545&origin=inward
ID information
  • DOI : 10.1021/acs.joc.8b03083
  • ISSN : 0022-3263
  • eISSN : 1520-6904
  • ORCID - Put Code : 53509717
  • Pubmed ID : 30656930
  • SCOPUS ID : 85061232545

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