THE SYNTHESIS OF FLUORANTHENE DERIVATIVES¹

Abstract

No simple way has yet been reported for preparing fluoranthene derivatives containing alkyl or aryl groups in which the position of the substituent is known. Most syntheses of fluoranthenes so far described (1, 2) require several steps. It has been found that the most suitable procedure is that of Dilthey (2) who treated acecyclone (III; R, R' = C-gH5) with maleic anhydride, and obtained the anhydride of 7,10-diphenylfluoranthene-8,9-dicarboxylic acid. Extension and modification of this procedure has led to the formation of a large number of new substituted fluoranthenes (VI), in which all the substituent groups are in the left-hand ring.The starting material is acenaphthenequinone, which is condensed with various alkyl ketones at 25-30°in methanol with an alkaline catalyst. As with benzil (3), three types of products result. Methyl n-alkyl ketones, in general, give carbinols (I) which, upon dehydration, do not give substituted cyclopentadienones but non-reversible dimers. Other ketones, however, give carbinols which may be dehydrated to a reversible dimer (II) or the corresponding monomeric cyclopentadienone (III). In some instances, the carbinol is unstable, even at 25-50°under the conditions of the condensation, so that the dienone results directly. The carbinols that are stable at room temperatures may also be converted to the cyclopentadienone by refluxing in alkaline solution. All these points of behavior were noted in our previous paper on simple substances (3).The structure of the dimer (II) has not been proved, but is written as shown

Efficient Blue‐Light‐Emitting Electroluminescent Devices with a Robust Fluorophore: 7,8,10‐Triphenylfluoranthene

“…Of particular note is the synthesis of fluoranthene derivatives by a double Knoevenagel condensation between 2-propanone and acenaphthenequinone, which allows functionalization at the carbon 7 and 10 positions. [7] A subsequent Diels-Alder addition allows further functionalization at the 8 and 9 positions. [7,8] Finally, starting from bromoacenapthenequinone, [9] the carbon 3 position is open to functionalization.…”

“…[7] A subsequent Diels-Alder addition allows further functionalization at the 8 and 9 positions. [7,8] Finally, starting from bromoacenapthenequinone, [9] the carbon 3 position is open to functionalization.…”

peri-Diketones with the ring system of cyclo-octa[de]naphthalene

“…The purple diester (6) was reduced by zinc and acetic acid, a reaction perhaps assisted by antiaromaticity, and the products were hydrolysed and decarboxylated before characterisation, to afford the ketones (18), (19), and (20). The ketone (20) was reduced to the known hydrocarbon (5), and this in three steps gave the desired peri-diketone (2) as outlined in Scheme 2. iii '8…”

Synthesis and Characterization of (7,10-Diphenyl Fluoranthene-8-)Silicon Compounds

“…7,9-diphenyl-8H-cyclopentacenaphthylene-8-one(DCPAO) was prepared according to the procedure outlined in reference [6] and its mp determined was 288.5-290.5"C (liter.29O"C). Vinyl-triethoxysilane was obtained from the Institute of Harbin Chemical Industry.…”