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| Content Provider | World Health Organization (WHO)-Global Index Medicus |
|---|---|
| Author | Kulinski, Janusz Jeszka, Jeremiasz K. Rózycka-sokolowska, Ewa Balczewski, Piotr Kania, Sylwester Marciniak, Bernard Bodzioch, Agnieszka Uznanski, Pawel |
| Description | Author Affiliation: Bodzioch A ( Department of Heteroorganic Chemistry, Center of Molecular and Macromolecular Studies, Polish Academy of Science, Sienkiewicza 112, 90-363 Lódz, Poland.) |
| 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. |
| ISSN | 09476539 |
| e-ISSN | 15213765 |
| Journal | Chemistry - A European Journal |
| Issue Number | 16 |
| Volume Number | 18 |
| Language | English |
| Publisher | Wiley-VCH;ChemPubSoc Europe |
| Publisher Date | 2012-04-16 |
| Publisher Place | Germany |
| Access Restriction | Open |
| Subject Keyword | Chemistry |
| Content Type | Text |
| Resource Type | Article |
| Subject | Organic Chemistry Catalysis |
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