Synthesis and photophysics of a 2,7-disubstituted donor-acceptor pyrene derivative: an example of the application of sequential ir-catalyzed c-h borylation and substitution chemistry

Lei Ji, Andreas Lorbach, Robert M. Edkins, Todd B. Marder

Research output: Contribution to journalArticle

38 Citations (Scopus)

Abstract

We report a general and selective method to synthesize 2,7-disubstituted pyrene derivatives containing two different substituents by sequential Ir-catalyzed borylation and substitution chemistry. To demonstrate the utility of our approach, we synthesized 2-cyano-7-(N,N-diethylamino)pyrene (3), a pyrene analogue of the widely studied chromophore 4-(N,N-dimethylamino)benzonitrile (DMABN). Compound 3 and the monosubstituted compounds 2-(N,N-diethylamino)pyrene (1) and 2-cyanopyrene (2) have been structurally characterized. Their electronic and optical properties have been studied by a combination of absorption and emission spectroscopies, lifetime and quantum yield measurements, and modeling by DFT and TD-DFT. The photophysical properties of 3 are compared to those of DMABN and 2-cyano-7-(N,N-dimethylamino)-4,5,9,10-tetrahydropyrene, and we show that 2,7-disubstituted pyrene is a moderately effective π-bridge for the construction of donor-acceptor compounds. It is also shown that donor or acceptor groups are only effective at the 2,7-positions of pyrene if they are suitably strong, leading to a switch in the energetic ordering of the HOMO-1 and HOMO or the LUMO and LUMO+1 of pyrene, respectively.

Original languageEnglish
Pages (from-to)5658-5665
Number of pages8
JournalJournal of Organic Chemistry
Volume80
Issue number11
DOIs
Publication statusPublished - 5 Jun 2015

Keywords

  • substitution chemistry
  • electronic and optical properties

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