Synthesis, Structures, and Physical Properties of Benzo[k]fluoranthene‐Based Linear Acenes

Abstract

This work describes the syntheses, crystal structures, photophysical properties, and electro-chemical analyses of benzo[k]fluoranthene-based linear acenes, together with ab initio density functional theory computations on them. The molecules were prepared in generally moderate to good yields through Pd-catalyzed cycloadditions between 1,8-diethynylnaphthalene derivatives and aryl iodides. This protocol is simpler and more efficient than conventional methods. The scope and limitations of this reaction were examined. The structures of compounds 4hb, 15ac, 17ab, 19ac, and 24je were determined by X-ray analysis; they are either bent or twisted, rather than planar. The photophysical and electrochemical properties of these cycloadducts were also investigated and compared with computational predictions based on density functional theory.

Highly Curved Bowl‐Shaped Fragments of Fullerenes: Synthesis, Structural Analysis, and Physical Properties

“…[14c] Pd-catalyzed annulation of 6 with iodoarenes 9 gave benzo[k]fluoranthene 10. [22] The low yield of 10 ac was unsurprising because our earlier studies revealed that substituted odiiodoarene exhibits better annulation than substituted monoiodoarene. Naphtho[1,2-k]cyclopenta[cd]fluoranthenes 12 were efficiently prepared by the simple Rh-catalyzed [(2 + 2) + 2] cycloaddition of diynes 6 with acenaphthylene (11 a), [14c] and were subsequently aromatized by treatment with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ).…”

Synthesis and Physical Properties of Novel 7, 12-Diaryl-<i>N</i>-phenylbenzo[<i>k</i>]fluoranthene-9, 10-dicarbox- imides

“…The emission quantum yields of 8a-8d were found high up to 0.97 (Table 2), while the emission quantum yield of 7, 12-diphenylbenzo [k]fluoranthene, which dose not have a dicarboximide moiety, is 0.48. [26] It is worthy to note that introduction of the dicarboximide moiety on this π-system has brought about a great advance in their emission efficiency. Further studies on cycloaddition of 4 for synthesis of π-extended arene-dicarboximides and their application to electronic devices are in progress.…”

Thioarylative Radical Cyclization of Yne-Dienone

“…11 Sonogashira cross-coupling of a labile Br group on the arene moiety of 5f with phenylacetylene furnished the alkynylation product 11 (83%) (eq 3, Scheme 6). 12 Thus, 3-thioarylated dihydrochromenone 3 is synthetically versatile.…”