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

Research output: Contribution to journalArticle

7 Citations (Scopus)

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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Fluorophores
Chemical activation
Oxygenation
Electrons
Cyclization
Chromophores
Excited states
Charge transfer
Optical properties
Fluorescence

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

Cite this

Żyła-Karwowska, M., Moshniaha, L., Hong, Y., Zhylitskaya, H., Cybińska, J., Chmielewski, P. J., ... 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
Żyła-Karwowska, Marika ; Moshniaha, Liliia ; Hong, Yongseok ; Zhylitskaya, Halina ; Cybińska, Joanna ; Chmielewski, Piotr J. ; Lis, Tadeusz ; Kim, Dongho ; Stępień, Marcin. / Electron-Deficient Bipyrrole Boomerangs : Bright Fluorophores Obtained via Double C−H Bond Activation. In: Chemistry - A European Journal. 2018 ; Vol. 24, No. 29. pp. 7525-7530.
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Żyła-Karwowska, M, Moshniaha, L, Hong, Y, Zhylitskaya, H, Cybińska, J, Chmielewski, PJ, Lis, T, Kim, D & Stępień, M 2018, 'Electron-Deficient Bipyrrole Boomerangs: Bright Fluorophores Obtained via Double C−H Bond Activation', Chemistry - A European Journal, vol. 24, no. 29, pp. 7525-7530. https://doi.org/10.1002/chem.201801199

Electron-Deficient Bipyrrole Boomerangs : Bright Fluorophores Obtained via Double C−H Bond Activation. / Żyła-Karwowska, Marika; Moshniaha, Liliia; Hong, Yongseok; Zhylitskaya, Halina; Cybińska, Joanna; Chmielewski, Piotr J.; Lis, Tadeusz; Kim, Dongho; Stępień, Marcin.

In: Chemistry - A European Journal, Vol. 24, No. 29, 23.05.2018, p. 7525-7530.

Research output: Contribution to journalArticle

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AU - Żyła-Karwowska, Marika

AU - Moshniaha, Liliia

AU - Hong, Yongseok

AU - Zhylitskaya, Halina

AU - Cybińska, Joanna

AU - Chmielewski, Piotr J.

AU - Lis, Tadeusz

AU - Kim, Dongho

AU - Stępień, Marcin

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Żyła-Karwowska M, Moshniaha L, Hong Y, Zhylitskaya H, Cybińska J, Chmielewski PJ et al. Electron-Deficient Bipyrrole Boomerangs: Bright Fluorophores Obtained via Double C−H Bond Activation. Chemistry - A European Journal. 2018 May 23;24(29):7525-7530. https://doi.org/10.1002/chem.201801199