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

doi:10.1002/chem.201801199

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

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

18 Citations (Scopus)

Abstract

Pd^II-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 language	English
Pages (from-to)	7525-7530
Number of pages	6
Journal	Chemistry - A European Journal
Volume	24
Issue number	29
DOIs	https://doi.org/10.1002/chem.201801199
Publication status	Published - 2018 May 23

Bibliographical note

Funding Information:
Financial support from the National Science Center of Poland (UMO-2014/13/B/ST5/04394, UMO-2015/19/N/ST5/00877) is gratefully acknowledged. Quantum chemical calculations were performed at the Wrocław Center for Networking and Supercomputing. The work at Yonsei University was supported by Strategic Research (NRF-2016R1E1A1A01943379) through the National Research Foundation of Korea (NRF) funded by the Ministry of Science, ICT (Information and Communication Technologies) and Future Planning.

Publisher Copyright:
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

All Science Journal Classification (ASJC) codes

Catalysis
Organic Chemistry

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10.1002/chem.201801199

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

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.",

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note = "Funding Information: Financial support from the National Science Center of Poland (UMO-2014/13/B/ST5/04394, UMO-2015/19/N/ST5/00877) is gratefully acknowledged. Quantum chemical calculations were performed at the Wroc{\l}aw Center for Networking and Supercomputing. The work at Yonsei University was supported by Strategic Research (NRF-2016R1E1A1A01943379) through the National Research Foundation of Korea (NRF) funded by the Ministry of Science, ICT (Information and Communication Technologies) and Future Planning. Publisher Copyright: {\textcopyright} 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

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AU - Hong, Yongseok

AU - Zhylitskaya, Halina

AU - Cybińska, Joanna

AU - Chmielewski, Piotr J.

AU - Lis, Tadeusz

AU - Kim, Dongho

AU - Stępień, Marcin

N1 - Funding Information: Financial support from the National Science Center of Poland (UMO-2014/13/B/ST5/04394, UMO-2015/19/N/ST5/00877) is gratefully acknowledged. Quantum chemical calculations were performed at the Wrocław Center for Networking and Supercomputing. The work at Yonsei University was supported by Strategic Research (NRF-2016R1E1A1A01943379) through the National Research Foundation of Korea (NRF) funded by the Ministry of Science, ICT (Information and Communication Technologies) and Future Planning. Publisher Copyright: © 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

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AB - 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.

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

Abstract

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