Fluorescent mesomorphic pyrazinacenes
The result's identifiers
Result code in 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>
Result on the web
<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>
Alternative languages
Result language
angličtina
Original language name
Fluorescent mesomorphic pyrazinacenes
Original language description
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.
Czech name
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Czech description
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Classification
Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CC - Organic chemistry
OECD FORD branch
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Result continuities
Project
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Continuities
S - Specificky vyzkum na vysokych skolach
Others
Publication year
2016
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Journal of Materials Chemistry C
ISSN
2050-7526
e-ISSN
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Volume of the periodical
4
Issue of the periodical within the volume
48
Country of publishing house
GB - UNITED KINGDOM
Number of pages
10
Pages from-to
11514-11523
UT code for WoS article
000390787600019
EID of the result in the Scopus database
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