Indanthrone dye revisited after sixty years

Abstract

Indanthrone, an old, insoluble dye can be converted into a solution processable, self-assembling and electroluminescent organic semiconductor, namely tetraoctyloxydinaptho[2,3-a:2 0 ,3 0 -h]phenazine (P-C8), in a simple one-pot process consisting of the reduction of the carbonyl group by sodium dithionite followed by the substitution with solubility inducing groups under phase transfer catalysis conditions.

Soluble Flavanthrone Derivatives: Synthesis, Characterization, and Application to Organic Light‐Emitting Diodes

“…Flavanthrone was transformed into 8,16‐dialkoxybenzo[ h ]benz[5,6]acridino[2,1,9,8‐ klmna ]acridines in a one‐pot process, previously elaborated for indanthrone . In the first step the carbonyl groups were reduced to phenolates by using Na 2 S 2 O 4 in sodium hydroxide solution, and then, without the necessity of intermediate product isolation, O ‐alkylation of phenolate groups was performed with alkyl bromides.…”

“…In recent years, synthetic strategies leading to new organic semiconductors in general, and to linear and nonlinear acenes and azaacenes in particular, frequently involved modification of old and sometimes almost‐forgotten dyes ,. In these cases the target azaacene core was first obtained in one step and then functionalized with solubilizing side groups such as triisopropylsilylethynyl by forming a −C≡C− linkage with the core in a second step .…”

“…Previously, we transformed indanthrone into a solution‐processable organic semiconductors, namely, 5,9,14,18‐tetraalkoxydinaphtho[2,3‐ a :2′,3′‐ h ]phenazines, in a simple one‐pot process consisting of the reduction of the carbonyl group by sodium dithionite followed by substitution with solubility‐inducing groups under phase‐transfer catalysis conditions ,. The resulting compounds showed high photoluminescence quantum yields and could be applied as electroluminophores in guest/host‐type LEDs.…”

Self-assembly of tetraalkoxydinaphthophenazines in monolayers on HOPG by scanning tunneling microscopy

“…In our recent communication [32] we have reported on a new group of solution processable, electroluminescent organic compounds, namely tetraalkoxydinaphtho[2,3-a:2′,3′-h]phenazines, which extend the family of already reported linear and non-linear azaacenes, widely studied in organic electronics as promising semiconductors [33][34][35][36][37][38]. These derivatives can be obtained from indanthrone-an old alizarin-type insoluble dye-in a relatively simple, one-pot preparation involving the carbonyl group reduction with sodium dithionite followed by the substitution with solubility inducing groups under the phase transfer catalysis conditions [32].…”

“…These derivatives can be obtained from indanthrone-an old alizarin-type insoluble dye-in a relatively simple, one-pot preparation involving the carbonyl group reduction with sodium dithionite followed by the substitution with solubility inducing groups under the phase transfer catalysis conditions [32]. This simple procedure enabled us to synthesize a series of tetraalkoxydinaphtho[2,3-a:2′,3′-h]phenazines with increasing length of the solubilizing substituent (from C4 to C12).…”