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Issue 48, 2016
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Fluorescent mesomorphic pyrazinacenes

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We report the synthesis of highly fluorescent pyrazinacenes (6,13-dihydrohexaazapentacene; fluorubine) containing groups at 6,13 positions that promote their solubility in non-polar organic solvents and their self-assembly properties. Hydrophilic 3,4,5-tris[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]benzyl (TEG3Bz) and hydrophobic 3,4,5-tris(1-n-dodecyloxy)benzyl (C123Bz) groups were incorporated in a series of compounds 1–9 where the fluorubine core was modified either by 2-bromination or by introduction of four peripheral benzo groups. Thus, 1–3 are respectively hydrophilic 6,13-(TEG3Bz)2, hydrophobic 6,13-(C123Bz)2 and amphiphilic 6-(TEG3Bz)(C123Bz) with 4–6 being the corresponding 2-brominated compounds and 7–9 the corresponding [a,c,l,n]-tetrabenzo compounds. Several of the compounds exhibit thermotropic mesophases: 4 and 7 have lamellar structures even at room temperature; 8 and 9 form columnar rectangular phases at higher temperatures. All the compounds are highly fluorescent exhibiting quantum yields (QY) up to 60% in solution. Solid state fluorescence spectra reveal that while the unmodified 6,13-dihydrohexaazapentacene compounds 1–3 maintain their large QYs in the solid state, 2-bromination (4–6) reduces the QY substantially (to 10% approx.). 7–9 give QY similar to 1–3 in solution but their QYs are attenuated in solid state due to chromophore aggregation.

Graphical abstract: Fluorescent mesomorphic pyrazinacenes

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Publication details

The article was received on 25 Oct 2016, accepted on 18 Nov 2016 and first published on 21 Nov 2016

Article type: Paper
DOI: 10.1039/C6TC04628B
Citation: J. Mater. Chem. C, 2016,4, 11514-11523
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    Fluorescent mesomorphic pyrazinacenes

    G. J. Richards, S. Ishihara, J. Labuta, D. Miklík, T. Mori, S. Yamada, K. Ariga and J. P. Hill, J. Mater. Chem. C, 2016, 4, 11514
    DOI: 10.1039/C6TC04628B

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