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2 article(s) from Kulhánek, Jiří

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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Review

Published 05 Jan 2012

Full text

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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Supp Info

Full Research Paper

Published 14 Apr 2009

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