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

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 fu...

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Published in:Chemistry : a European journal 2018-05, Vol.24 (29), p.7525-7530
Main Authors: Żyła‐Karwowska, Marika, Moshniaha, Liliia, Hong, Yongseok, Zhylitskaya, Halina, Cybińska, Joanna, Chmielewski, Piotr J., Lis, Tadeusz, Kim, Dongho, Stępień, Marcin
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Language:English
Subjects:
Activation
Charge transfer
Chemical compounds
Chemistry
Chromophores
C−H activation
Electrons
Fluorescence
Fluorophores
helical structures
heterocycles
Intermediates
Optical properties
Oxygenation
Polarity
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cited_by cdi_FETCH-LOGICAL-c4769-754d29bcc97af086c3eda4768e3367d0e4583ef6dbec5aa92f805e559522623c3
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container_end_page 7530
container_issue 29
container_start_page 7525
container_title Chemistry : a European journal
container_volume 24
creator Żyła‐Karwowska, Marika
Moshniaha, Liliia
Hong, Yongseok
Zhylitskaya, Halina
Cybińska, Joanna
Chmielewski, Piotr J.
Lis, Tadeusz
Kim, Dongho
Stępień, Marcin
description 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. Break it with a boomerang! A new family of aromatic molecules with a distinct boomerang shape (see graphic) has been developed through annulative double C−H bond activation. This chemistry provides access to boomerangs with variable bends and twists, and tunable donor–acceptor properties. These new chromophores fluoresce strongly in solvents of varying polarity and undergo photoinduced intramolecular charge transfer in the excited state.
doi_str_mv 10.1002/chem.201801199
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subjects Activation
Charge transfer
Chemical compounds
Chemistry
Chromophores
C−H activation
Electrons
Fluorescence
Fluorophores
helical structures
heterocycles
Intermediates
Optical properties
Oxygenation
Polarity
title Electron‐Deficient Bipyrrole Boomerangs: Bright Fluorophores Obtained via Double C−H Bond Activation
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