Aromatic hydrocarbons. Part LXVI. Diperinaphthyleneanthracenes

Synthesis of Nitrogen‐Containing Rubicene and Tetrabenzopentacene Derivatives

“…By comparison, the spectrum obtained for 9 was broadened and red-shifted (presumably due to the molecules expanded aromatic system), with prominent absorption peaks at 400 nm and 524 nm ( Figure 2). Likewise,w ef ound that the spectra for 5 and 10 were similar to the ones reported for tetrabenzopentacene [36,37,44] and other pentacene derivatives. [7,8,26,27] The spectrum obtained for 5 featured acluster of three characteristic absorption peaks at 555 nm, 600 nm, and 650 nm ( Figure 2).…”

“…Herein, we report the preparation of previously unknown rubicene [34,35] and tetrabenzopentacene [36,37] variants,w hich can be viewed either as acene derivatives or as molecular fragments of fullerenes and GNRs.I no ur strategy,w ef irst synthesize difunctional halogenated building blocks and convert them to derivatized anthracene precursors via the aza-Diels-Alder (Povarov) reaction. [38,39] Subsequently,w e use either the Heck coupling [40,41] to form two 5-membered fused rings or base-mediated cyclodehydrohalogenation [42,43] to form two 6-membered fused rings within the anthracene skeletal frameworks,obtaining nitrogen-containing rubicenes or tetrabenzopentacenes,r espectively.W ei nt urn characterize these molecules with spectroscopic techniques,e lectrochemical measurements,and density functional theory calculations.O ur general methodology provides facile access to novel materials,w hich hold promise both as electron transporting organic semiconductors and as model compounds for larger carbonaceous systems.…”

“…Fort he design of our nitrogen-doped compounds,w e sought inspiration from the classic all-carbon rubicene [34,35] and tetrabenzopentacene [36,37] motifs ( Figure 1b). Although these molecules were synthesized > 60 years ago,their nitrogen-containing analogues have never been reported (to the best of our knowledge), and tetrabenzopentacene is even still prepared via arelatively limited and harsh method.…”

Effect of overcrowding in mass spectra for six violanthrenes

“…IsoVEB'~ and TBP13 were prepared as the two main components of a mixture product by the reduction of benzanthrone with copper powder and then separated from one another.14*15 TBPA was prepared by the condensation of 1,5-dichloroanthraquinone with 1naphthylmagnesium bromide, followed by reduction with hydrogen iodide, and cyclization with potassium hydroxide in quinoline. 16 The identities of the products were checked by comparing the results of several different methods of syntheses.…”

Refined molecular structure of tetrabenzo[de,hi,op,st]pentacene

“…The title compound was prepared by the literature method (Clar, Kelly & Wright, 1954). The sample contains impurities which could not be removed by recrystaUization or vacuum sublimation methods.…”