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3 article(s) from Bureš, Filip

Structure–property relationships and third-order nonlinearities in diketopyrrolopyrrole based D–π–A–π–D molecules

Jan Podlesný,
Lenka Dokládalová,
Oldřich Pytela,
Adam Urbanec,
Milan Klikar,
Numan Almonasy,
Tomáš Mikysek,
Jaroslav Jedryka,
Iwan V. Kityk and
Filip Bureš

Beilstein J. Org. Chem. 2017, 13, 2374–2384, doi:10.3762/bjoc.13.235

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Graphical Abstract

Figure 1: General structure of investigated DPP derivatives 1–5.

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Scheme 1: Synthesis of target DPP chromophores 1–5. (i) PdCl₂(PPh₃)₂, Na₂CO₃, THF, H₂O; (ii) PdCl₂(PPh₃)₂, TH...

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Figure 2: Thermograms of representative chromophores 4a and 4b.

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Figure 3: Energy level diagram of the electrochemical (black) and DFT (red) derived energies of the E_HOMO/LUMO...

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Figure 4: UV–vis absorption spectra of chromophores 1a and 1b in 1,4-dioxane at a concentration of 1 × 10⁻⁵ M....

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Figure 5: UV–vis absorption spectra of chromophores 1b–5b in 1,4-dioxane at a concentration of 1 × 10⁻⁵ M.

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Figure 6: Typical THG dependences vs the fundamental energy density.

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Figure 7: HOMO (red) and LUMO (blue) localizations in 1a (ethylhexyl chains truncated).

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Full Research Paper

Published 08 Nov 2017

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Imidazole as a parent π-conjugated backbone in charge-transfer chromophores

Jiří Kulhánek and
Filip Bureš

Beilstein J. Org. Chem. 2012, 8, 25–49, doi:10.3762/bjoc.8.4

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Graphical Abstract

Figure 1: Schematic representation of organic D-π-A system featuring ICT.

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Figure 2: Two principal orientations of the imidazole-derived charge-transfer chromophores.

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Scheme 1: Common synthetic approach to triarylimidazole-, diimidazole-, and benzimidazole-derived CT chromoph...

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Scheme 2: Syntheses of important 4,5-dicyanoimidazole derivatives 1–3 [27-30].

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Figure 3: Donor–acceptor triaryl push–pull azoles 4a–h [31,32].

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Figure 4: Y-shaped CT chromophores with an extended π-conjugated pathway and various donor and acceptor subst...

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Figure 5: Molecular structures of chromophores 9–14 [13,15,37-41].

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Figure 6: General structure of 4,5-bis(4-aminophenyl)imidazole-derived chromophores 15a–g with various π-link...

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Figure 7: Various orientations of the substituents on the parent lophine π-conjugated backbone (16–19) and th...

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Figure 8: Structure and electronic absorption spectra of chromophores 21–26 [12].

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Figure 9: Typical D-π-A diimidazole CT chromophore [16-18,50-53].

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Figure 10: Typical D-π-D diimidazoles 28–31 [19,54-56] and photochromic diimidazoles 32,33 [57,58].

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Scheme 3: Oxidation of 1H-diimidazoles to 2H-diimidazoles (quinoids).

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Figure 11: Typical benzimidazoles-derived D-π-A push–pull systems 35–43 [25,62-66].

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Figure 12: Structure of benzimidazoles (44–47), imidazophenanthrolines (48–57), imidazophenanthrenes (58–60), ...

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Scheme 4: Acidoswitchable NLO-phores 64,65 and ESIPT mechanism [72-74].

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Figure 13: General structures of bis(benzimidazole) chromophores 67–71 and pyridinium betaines 72 [75-79].

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Figure 14: Overview of 4,5-dicyanoimidazole derivatives investigated by Rasmussen et al. [29,81-94].

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Figure 15: 4,5-Dicyanoimidazole-derived chromophores 84–87 [103-106].

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Figure 16: Push–pull chromophores 88–93 with systematically extended π-linker [30].

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Figure 17: pH-triggered NLO switches 88c–93c [109].

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Figure 18: Dibromoolefin 94 and branched chromophores 95–100 [112,113].

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Figure 19: Imidazole as a donor–acceptor unit in CT-chromophores 101–111 [20].

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Figure 20: Diimidazoles 112–115 used as small electron acceptors in organic solar cells [115,116].

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Figure 21: Amino- and hydroxy-functionalized chromophores incorporated into a polymer backbone R^pol [18,50-53,122-124].

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Figure 22: Structure of polyphosphazene polymers bearing NLO-phores [125-127] and some other recent examples of nonline...

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Figure 23: Epoxy- and silica-based polymers functionalized with 4,5-dicyanoimidazole unit [105,130].

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Published 05 Jan 2012

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Convenient methods for preparing π-conjugated linkers as building blocks for modular chemistry

Jiří Kulhánek,
Filip Bureš and
Miroslav Ludwig

Beilstein J. Org. Chem. 2009, 5, No. 11, doi:10.3762/bjoc.5.11

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Figure 1: Basic and newly proposed π-conjugated linkers designed for the Suzuki–Miyaura and Sonogashira cross...

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Scheme 1: Convenient synthetic methods leading to π-linkers 3–6.

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Scheme 2: Sonogashira cross-coupling leading to π-linkers 7c–9c.

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Published 14 Apr 2009

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