Fluorescent mesomorphic pyrazinacenes

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216275%3A25310%2F16%3A39902357" target="_blank" >RIV/00216275:25310/16:39902357 - isvavai.cz</a>

Výsledek na webu

<a href="http://pubs.rsc.org/en/content/articlelanding/2016/tc/c6tc04628b#!divAbstract" target="_blank" >http://pubs.rsc.org/en/content/articlelanding/2016/tc/c6tc04628b#!divAbstract</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1039/c6tc04628b" target="_blank" >10.1039/c6tc04628b</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Fluorescent mesomorphic pyrazinacenes

Popis výsledku v původním jazyce

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.

Název v anglickém jazyce

Fluorescent mesomorphic pyrazinacenes

Popis výsledku anglicky

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.

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

CC - Organická chemie

OECD FORD obor

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Projekt

—

Návaznosti

S - Specificky vyzkum na vysokych skolach

Rok uplatnění

2016

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Journal of Materials Chemistry C

ISSN

2050-7526

e-ISSN

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Svazek periodika

4

Číslo periodika v rámci svazku

48

Stát vydavatele periodika

GB - Spojené království Velké Británie a Severního Irska

Počet stran výsledku

10

Strana od-do

11514-11523

Kód UT WoS článku

000390787600019

EID výsledku v databázi Scopus

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