Practical Synthesis of Unsymmetrical Tetraarylethylenes and Their Application for the Preparation of [Triphenylethylene−Spacer−Triphenylethylene] Triads

• Published in: Journal of organic chemistry Vol. 72; no. 21; pp. 8054 - 8061
• Main Authors: Banerjee, Moloy, Emond, Susanna J, Lindeman, Sergey V, Rathore, Rajendra
• Format: Journal Article
• Language: English
• Published: Washington, DC American Chemical Society 12.10.2007
• Subjects: Chemistry; Exact sciences and technology; Noncondensed benzenic compounds; Organic chemistry; Preparations and properties; Substituent effect; Benzophenone derivatives; Purification; Asymmetric molecule; Phenylene polymer; Phenylene derivative polymer; Oxidation potential; Tertiary alcohol; Electrochemistry; Benzenic compound; Triad; Chemical synthesis; Ethylenic compound
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo701474y

We have demonstrated that reactions of diphenylmethyllithium with a variety of substituted benzophenones produces corresponding tertiary alcohols that are easily dehydrated, without any need for purification, to produce various unsymmetrical and symmetrical tetraarylethylenes in excellent yields. The simplicity of the method allows for the preparation of a variety of ethylenic derivatives in multigram (10−50 g) quantities with great ease. The methodology was successfully employed for the preparation of various triphenylethylene (TPE)-based triads (i.e., TPE−spacer−TPE) containing polyphenylene and fluoranyl-based spacers. The ready availability of various substituted tetraarylethylenes allowed us to shed light on the effect of substituents on the oxidation potentials (E ox) of various tetraarylethylenes. Moreover, the electronic coupling among the triphenylethylene moieties in various TPE−spacer−TPE triads was briefly probed by electrochemical and optical methods.