Perylene, Oligorylenes, and Aza-Analogs

Abstract

An in-depth discussion of the properties of perylene is presented. Tuning the properties of perylene by introducing nitrogens is also explored. Finally, we do not discuss the synthesis and properties of oligorylenes functionalized with dicarboxyimide bonds.

Studies on Pyrene and Perylene Derivatives upon Oxidation and Application to a Higher Analogue

“…69 Furthermore, early theoretical calculations have indicated the neutral polyrylene as either parallel polyacetylene chains (Figure 17b), or a planar poly( p-phenylene) bridged by double bonds (Figure 17c). 70,71 It is proved that the end groups or doping affect the whole electronic structure of the polyrylene.…”

Cyclic Alkyne Approach to Heteroatom-Containing Polycyclic Aromatic Hydrocarbon Scaffolds

“…Cyclohexyne (23), and heterocyclic strained cyclic alkynes 25 [13] and 26 [16] performed smoothly (entries 4-6). [33,31] Aseries of differentially-substituted oxadiazinones were prepared using established chemistry [45] and subjected to silyl triflate 11 under our standard reaction conditions ( Figure 5). [6,13,16] We also sought to access products bearing differing C and D rings.A sn oted earlier, in most routes to 9,10-anthracene derivatives,t he C and D rings are introduced through ad ouble cross-coupling or by the double addition of an organometallic reagent, allowing for the formation of only symmetric products with limited functional group compatibility.…”

“…[6,13,16] We also sought to access products bearing differing C and D rings.A sn oted earlier, in most routes to 9,10-anthracene derivatives,t he C and D rings are introduced through ad ouble cross-coupling or by the double addition of an organometallic reagent, allowing for the formation of only symmetric products with limited functional group compatibility. [31] A3-component coupling of two different silyl triflates, 11 and 32,a nd oxadiazinone 12 was performed ( Figure 6). Thed esired sequence took place to deliver pyrone isomers 28-31 in yields ranging from 66 to 84 %.…”

“…[29] Novel derivatives of 1 have been highly sought. [31][32][33] Heteroatoms may be included in the anthracene ring itself or on the C9/C10 substituents,a se xemplified by 2 [34][35][36][37] and 3, [38] respectively ( Figure 1), which can impact material properties. [31][32][33] Heteroatoms may be included in the anthracene ring itself or on the C9/C10 substituents,a se xemplified by 2 [34][35][36][37] and 3, [38] respectively ( Figure 1), which can impact material properties.…”

“…Fore xample,t he assembly of nonsymmetric PA Hs that possess multiple functional groups usually requires long linear sequences. [31,43] We targeted the synthesis of scaffold 7 through an ambitious approach, whereby ring fragments A-D could be united with formation of the central benzene ring (Figure 2a). [33,13] Lastly,v ariation at C9 and C10 is primarily achieved via the use of strongly basic organometallic reagents or transition metal catalysis,a nd typically results in symmetric molecules or low yields.…”