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Bodzioch A, Marciniak B, Różycka-Sokołowska E, et al. Synthesis and optoelectronic properties of hexahydroxylated 10-O-R-substituted anthracenes via a new modification of the Friedel-Crafts reaction using O-protected ortho-acetal diarylmethanols. Chemistry. 2012;18(16):4866-76doi: 10.1002/chem.201101909.
Bodzioch, A., Marciniak, B., Różycka-Sokołowska, E., Jeszka, J. K., Uznański, P., Kania, S., Kuliński, J., & Bałczewski, P. (2012). Synthesis and optoelectronic properties of hexahydroxylated 10-O-R-substituted anthracenes via a new modification of the Friedel-Crafts reaction using O-protected ortho-acetal diarylmethanols. Chemistry (Weinheim an der Bergstrasse, Germany), 18(16), 4866-76. https://doi.org/10.1002/chem.201101909
Bodzioch, Agnieszka, et al. "Synthesis and optoelectronic properties of hexahydroxylated 10-O-R-substituted anthracenes via a new modification of the Friedel-Crafts reaction using O-protected ortho-acetal diarylmethanols." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 18,16 (2012): 4866-76. doi: https://doi.org/10.1002/chem.201101909
Bodzioch A, Marciniak B, Różycka-Sokołowska E, Jeszka JK, Uznański P, Kania S, Kuliński J, Bałczewski P. Synthesis and optoelectronic properties of hexahydroxylated 10-O-R-substituted anthracenes via a new modification of the Friedel-Crafts reaction using O-protected ortho-acetal diarylmethanols. Chemistry. 2012 Apr 16;18(16):4866-76. doi: 10.1002/chem.201101909. Epub 2012 Mar 21. PMID: 22438194.
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Chemistry. 2012 Apr 16;18(16):4866-76. doi: 10.1002/chem.201101909. Epub 2012 Mar 21.

Synthesis and optoelectronic properties of hexahydroxylated 10-O-R-substituted anthracenes via a new modification of the Friedel-Crafts reaction using O-protected ortho-acetal diarylmethanols.

Chemistry (Weinheim an der Bergstrasse, Germany)

Agnieszka Bodzioch, Bernard Marciniak, Ewa Różycka-Sokołowska, Jeremiasz K Jeszka, Paweł Uznański, Sylwester Kania, Janusz Kuliński, Piotr Bałczewski

Affiliations

  1. Department of Heteroorganic Chemistry, Center of Molecular and Macromolecular Studies, Polish Academy of Science, Sienkiewicza 112, 90-363 ?ód?, Poland.

PMID: 22438194 DOI: 10.1002/chem.201101909

Abstract

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.

Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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