A new modification of the Friedel-Crafts type intramolecular cyclization involving O-protected ortho-acetal diarylmethanols as a new type of reactant, was carried out for the first time in a medium containing a large amount of water at room temperature and enabled synthesis of a series of electron-rich, hexahydroxylated 10-O-R-substituted anthracenes, where R is an alkyl (Me, nBu, n-C(16)H(33)) or arylalkyl group (CH(2)Ph, CH(2)-2-Napht, CH(2)C(6)H(4)CH(2)OAr) and also evaluation of their electronic and optoelectronic properties in solution, crystal, and solid thin film. In this transformation, a central 10-O-R-substituted benzene ring was formed, fused to rings originating from two independent aromatic aldehydes. The reaction proceeded via two identified mechanisms involving acetal and/or free aldehyde groups. The acid sensitive acetal and dibenzyl alkoxy functions have never been used together in the intramolecular Friedel-Crafts type cyclization. The new compounds revealed deep blue fluorescence and quantum yields in solution around 0.3. The electrical properties investigated for thin films obtained by vacuum deposition on glass were 10-O-R-substituent dependent and showed much faster transient current decay in the case of the 10-O-CH(2)Ph derivative than for the material with a 10-O-Me substituent (the lifetime of charge carriers was 25 times shorter in this case). The AFM images of thin films, Stokes shifts, and X-ray analysis of π-stacking interactions in crystals of the new materials have been also obtained.

The kinetics of activation currents induced by ethanol into thin layers of two aromatic hydrocarbons were investigated. The results indicate a partial chemisorption process with injection of carriers. Assuming that the increase of the current over the initial value is proportional to the covered surface, the enthalpies determined from the slope of the C 2 H 5 OH adsorption dependence were nearly identical for tetracene and for p-quaterphenyl. This suggests a similar mechanism for the effect of adsorption on the electron structure of the adsorbing molecule for both of the substances. Variations of the conductivity were observed due to the adsorption of ethanol, which suggests that hopping through localized states is the dominant mode of charge transport.

Diarylmethyl ethers (I) bearing an ortho‐acetal group at one arene ring undergo the cyclization under much milder reaction conditions compared to reported similar cyclization methods.

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