Electron-Deficient Bipyrrole Boomerangs: Bright Fluorophores Obtained via Double C−H Bond Activation

Marika Żyła-Karwowska, Liliia Moshniaha, Yongseok Hong, Halina Zhylitskaya, Joanna Cybińska, Piotr J. Chmielewski, Tadeusz Lis, Dongho Kim, Marcin Stępień

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Abstract

PdII-mediated annulative double C−H activation is shown to efficiently convert 1,n-dipyrrolylalkanes into extensively π-conjugated bipyrroles not accessible by conventional oxidative coupling protocols. This approach is applicable to both electron-rich and electron-deficient systems, and has been further developed into tandem processes involving further cyclization of substituents or oxygenation of pyrrolic α-positions. The new bipyrrole intermediates show enhanced fluorescence as well as tunable optical properties controlled by the alignment of chromophore subunits. Photophysical data, including femtosecond transient absorptions, reveal solvent-induced intramolecular charge transfer in their excited states, dependent on the polarity of the medium.

Original languageEnglish
Pages (from-to)7525-7530
Number of pages6
JournalChemistry - A European Journal
Volume24
Issue number29
DOIs
Publication statusPublished - 2018 May 23

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All Science Journal Classification (ASJC) codes

  • Chemistry(all)

Cite this

Żyła-Karwowska, M., Moshniaha, L., Hong, Y., Zhylitskaya, H., Cybińska, J., Chmielewski, P. J., Lis, T., Kim, D., & Stępień, M. (2018). Electron-Deficient Bipyrrole Boomerangs: Bright Fluorophores Obtained via Double C−H Bond Activation. Chemistry - A European Journal, 24(29), 7525-7530. https://doi.org/10.1002/chem.201801199