Synthesis and Characterization of Soluble Oligo(9,10‐anthrylene)s

Abstract

A homologous series of oligo(9,lO-anthry1ene)s up to the heptamer have been synthesized by reductive coupling of quinones with lithioanthrylenes, followed by reductive aromatization of the intermediate hydroxy species. The method used allows the introduction of different alkyl substituents, which ensure sufficient solubility of the newly synthesized anthrylene systems in common organic solvents. The solidstate conformations of trimers 4 and 5 have been established by X-ray structure analysis; UV/Vis-spectroscopic investiga-tions in solution reveal the anthratene moieties in 9,lO-anthrylenes to exist as electronically independent electrophores. The trianthrylenes can b e subjected to electrophilic substitution which regioselectively provides e.g. 10-bromo-and 10,lO"-dibromo derivatives. These bromides can easily b e converted into the corresponding cyano compounds. Under the influence of potassium hydroxide in quinoline the trimer 5 partially cyclizes to helianthrene compounds.

Boron‐Doped Tri(9,10‐anthrylene)s: Synthesis, Structural Characterization, and Optoelectronic Properties

“…Thus, we cannot unambiguously assign a specific signal set to either 4 or 4′ . Similar rotamers have previously been reported for a 4 ‐type tri(9,10‐anthrylene), in which the DBA core is replaced by 2,6‐di‐ tert ‐butylanthracene‐9,10‐diyl and for which the sterically less congested atropisomer corresponding to 4′ is preferentially formed and has been structurally characterized 33…”

“…The products were conveniently separated by selective extraction of the 2,7‐isomer into acetone (see the Supporting Information). Treatment of 2,6‐di‐ tert ‐butylanthracene with N ‐bromosuccinimide/FeCl 3 in CHCl 3 gave 1 (Scheme ) in excellent yield 33. Lithium–bromine exchange on compound 1 with n BuLi, followed by the addition of 9,10‐dibromo‐DBA ( 3 ; Scheme ) led to the formation of the 9,10‐dianthryl‐DBAs 4 and 4′ (Scheme ).…”

“…[24][25][26] Because the radiative back transition from the TICT state to the ground state is overlap forbidden, many TICT states are nonluminescent and therefore lead to intramolecular fluorescence quenching. However, by coupling to suitable vibrations this transition can gain intensity from more allowed states, [24] which explains the appreciable TICT fluorescence quantum yields of various compounds like, for example, oligo(9,10-anthrylene)s. [27][28][29][30][31][32][33][34][35] Herein, we report on the synthesis and structural characterization of compounds D carrying electronically innocent (i.e., Ph), potentially p-accepting (i.e., Mes 2 B), and p-donating (i.e., Tol 2 N; Tol = p-tolyl) substituents R 3 . These com-pounds can be regarded as boron-doped analogues of tri(9,10-anthrylene)s and a comparison of the optoelectronic properties of the two classes of compounds will therefore be revealing.…”

π-Conjugated Anions: From Carbon-Rich Anions to Charged Carbon Allotropes

“…[69,70] For 9,9Ј-bianthryl 36, the rotational barrier increases, and the system adopts a ground state conformation with an inter-ring angle of nearly 90°. [71,72] This conformational change leads to only a small interaction between the two subunits in 36 as compared with that in 35. Only a small potential difference is observed between the first and second electron transfers in 36.…”

Novel red light emitting 9,10-bis(phenylethynyl)anthracenes

“…8 Also, the introduction of different pendant alkyl substituents can lead to a significant increase in solubility and reduction of self-quenching due to the intermolecular π-π overlap. [9][10][11] Bearing in mind these findings we wish to report herein an easy synthesis of simple and novel π-conjugated systems which are highly luminescent in the red region and have possibilities for use as new red dopants.…”