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Azobenzene-Based Organic Salts with Ionic Liquid and Liquid Crystalline Properties

TitleAzobenzene-Based Organic Salts with Ionic Liquid and Liquid Crystalline Properties
Publication TypeJournal Article
Year of Publication2015
AuthorsStappert, K, Muthmann, J, Spielberg, ET, Mudring, AV
Journal Design
Volume15
Pagination4701-4712
Date Published09
Type of ArticleArticle
ISBN Number1528-7483
Accession NumberWOS:000360867300060
Keywordsanisotropy, behavior, films, solvents, storage, surfactants
Abstract

(Cn-Im) bearing a terminal azobenzene unit (C1-Azo) substituted with an alkoxy chain (O-Cm) of either two (2) or six (3) carbon atoms: [C1-Azo-O-Cm-Im-Cn]; m = 2, n = 8, 10, 12 and m = 6, n = 8, 10, 12, 14, 16. For both cation classes, the influence of alkyl chains of varying length on the thermal phase behavior was investigated by differential scanning calorimetry (DSC) and polarizing optical microscopy (POW. For five compounds (Azo(-C1-Im-C12)(2) (Id), Azo(-C1-Im-C12)(2) (1e), C1-Azo-O-C2-Im-C10 (2b), C1-Azo-O-C2-Im-C12 (2c), and C1-Azo-O-C6-Im-C16 (3e)), the formation of a liquid crystalline phase was observed. The biscationic salts (1) are all comparatively high melting organic salts (180-240 degrees C), and only the two representatives with long alkylchains (C12 and C14) exhibit liquid crystallinity. The monocationic salts with an O-C2 bridge (2) melt between 140 and 170 degrees C depending on the alkyl chain length, but from an alkyl chain of 10 and more carbon atoms on they form a smectic A liquid crystalline phase. The representatives of the third set with a O-C6 bridge qualify as ionic liquids with melting points less than 100 degrees C. However, only the representative with a hexadecyl chain forms a liquid crystalline phase. Representative single crystals for all sets of cations could be grown that allowed for single crystal structure analysis. Together with small-angle X-ray scattering experiments they allow for a more detailed understanding of the thermal properties. Through irradiation with UV-light (320-366 nm) all compounds undergo trans-cis isomerization, which reverses under visible light (440 nm).

DOI10.1021/acs.cgd.5b01024
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