Electrogenerated chemiluminescence of N,N-dimethylamino functionalized tetrakis(phenylethynyl)pyrenes

Yeon Ok Lee, Tuhin Pradhan, Kihang Choi, Dong Hoon Choi, Joung Hae Lee, Jong Seung Kim

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

The synthesis of star-shaped molecules, comprising a pyrene core with tetrakis(phenylethynyl) arms substituted with N,N-dimethylamino and propyl groups (1-5), is reported. The electrochemical and photophysical properties of 1-5 depend on the number of N,N-dimethylamino groups on the tetrakis(phenylethynyl)pyrene framework. In electrogenerated chemiluminescence (ECL) studies, the spectra of 4 and 5 show red-shifts and band broadening; in contrast, 1 exhibits a typical high-intensity pyrene ECL emission. It was confirmed that the ECL spectra arise from the intramolecular charge transfer (ICT) induced by the annihilation of radical ions owing to the presence of a strong donor.

Original languageEnglish
Pages (from-to)5908-5912
Number of pages5
JournalTetrahedron
Volume69
Issue number29
DOIs
Publication statusPublished - 2013 Jul 22

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Pyrenes
Chemiluminescence
Luminescence
Stars
Charge transfer
Ions
Molecules
pyrene

Keywords

  • Intramolecular charge transfer (ICT)
  • Radical stability
  • Substitution N,N-dimethylamino group
  • Tetrakis(phenylethynyl)pyrene

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Electrogenerated chemiluminescence of N,N-dimethylamino functionalized tetrakis(phenylethynyl)pyrenes. / Lee, Yeon Ok; Pradhan, Tuhin; Choi, Kihang; Choi, Dong Hoon; Lee, Joung Hae; Kim, Jong Seung.

In: Tetrahedron, Vol. 69, No. 29, 22.07.2013, p. 5908-5912.

Research output: Contribution to journalArticle

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AU - Pradhan, Tuhin

AU - Choi, Kihang

AU - Choi, Dong Hoon

AU - Lee, Joung Hae

AU - Kim, Jong Seung

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AB - The synthesis of star-shaped molecules, comprising a pyrene core with tetrakis(phenylethynyl) arms substituted with N,N-dimethylamino and propyl groups (1-5), is reported. The electrochemical and photophysical properties of 1-5 depend on the number of N,N-dimethylamino groups on the tetrakis(phenylethynyl)pyrene framework. In electrogenerated chemiluminescence (ECL) studies, the spectra of 4 and 5 show red-shifts and band broadening; in contrast, 1 exhibits a typical high-intensity pyrene ECL emission. It was confirmed that the ECL spectra arise from the intramolecular charge transfer (ICT) induced by the annihilation of radical ions owing to the presence of a strong donor.

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