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Fluorescent mesomorphic pyrazinacenes

Authors: Richards Gary J. | Ishihara Shinsuke | Labuta Jan | Miklík David | Mori Toshiyuki | Yamada Shinji | Ariga Katsuhiko | Hill Jonathan P.

Year: 2016

Type of publication: článek v odborném periodiku

Name of source: Journal of Materials Chemistry C

Page from-to: 11514-11523

Titles:

Language	Name	Abstract	Keywords
cze	Fluorescentní mezomorfní pyrazinaceny	Je popsána syntéza vysoce fluorescentních pyrazinacenů (6,13-dihydrohexaazapentacen; fluorubin), které v polohách 6 a 13 nesou skupiny zvyšující jejich samoorganizující vlastnosti a jejich rozpustnost v nepolárních organických rozpouštědlech. Některé sloučeniny vykazují termotropní mezofáze: při laboratorní teplotě mají lamelární struktury, jiné mají při vyšších teplotách sloupovou strukturu. Byla měřena fluorescenční spektra všch látek v pevné fázi.	pyrazinaceny; fluorescence; mezofáze
eng	Fluorescent mesomorphic pyrazinacenes	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.	pyrazinacenes; fluorescence; mesophases