Electroluminescence and electron–hole mobility of 6,12-di(thien-2-il)indolo[3,2-b]carbazoles

An improved protocol for the preparation of 5,11-dialkyl-6,12-di(hetero)aryl-5,11-dihydroindolo[3,2-b]carbazoles and synthesis of their new 2,8-dicyano- / 2,8-bis(benzo[d]thiazol-2-yl)-substituted derivatives

“…It should be noted, that current procedure for preparation of ICZs 3 is fully applicable for their multigram scale syntheses. Further alkylation of ICZ compounds 3 proceeded smoothly at their treatment with long-chain alkyl bromides, namely 1-bromohexane and 1-bromododecane, in the presence of potassium tert-butoxide in dry DMSO solution for 1 h, affording derivatives 4 (Table 1, entries [11][12][13][14][15][16][17][18][19][20]. The latter ICZ compounds have been used for preparation of their 2,8-diformyl-substituted derivatives by the Rieche formylation.…”

“…In general, this is due to the fact that π-conjugated and rigid planar indolo [3,2b]carbazole ring system has a number of useful optical and electronic properties, as well as high thermal, photo-and electrochemical stability as well as high resistance toward oxidation by air oxygen. [9][10][11][12][13] Thus, a number of ICZ derivatives, bearing (hetero)aromatic substituents at main scaffold, have been applied as electroluminescent and charge-transport materials for organic light-emitting diodes (OLEDs) [14][15][16][17][18] and organic field-effect transistors (OFETs), [19][20][21][22] as well as light-harvesting dyes for organic photovoltaics (OPVs). [23][24][25][26] In particular, some structures of such materials are presented in Figure 1.…”