Organic Microelectronics:  Design, Synthesis, and Characterization of 6,12-Dimethylindolo[3,2-b]Carbazoles

Abstract

spectra were recorded on a Varian AS400 apparatus in appropriated deuterated solvent solution at 298 K. Chemical shifts were reported as δ values (ppm) relative to internal tetramethylsilane. Differential scanning calorimetry (DSC) was performed on Perkin-Elmer DSC7 module in conjunction with the Perkin-Elmer thermal analysis controller TAC7/DX at a heating rate of 2°C/min. UV-visible absorption spectra were recorded on a Hewlett-Packard diode-array spectrophotometer (model 8452A) using 1 cm path length quartz cells. Optical band gap was calculated from the onset of the UV-visible absorption band. For the solid state measurement, oligomer solution in THF was cast on a quartz plates. Cyclic voltammetry was carried out in a two-compartment cell with a Solartron potentiostat (model 1287) with a platinum electrodes at a scan rate of 50 mV/s against SCE reference electrode in an anhydrous and argonsaturated solution containing tetrabutylammonium perchlorate (TBAP) (10 -1 M) and oligomer (10 -4 M) in THF. Materials.All starting organic compounds were purchased from Aldrich Co. and used without further purification. All solvents used in the reactions were freshly distilled under argon. The supporting electrolyte tetrabutylammonium perchlorate was previously dried under vacuum at 60°C. Syntheses of 2,5-dimethyl-4-methoxyphenylboronic acid, 1 Pd(PPh 3 ) 4 , 2 PdCl 2 (dppf) 3 have been already reported in the literature. 2,5-dimethyl-4-(2'-nitrophenyl)anisole (1).A two-necked 500 mL flask fitted with condenser, magnetic stirring bar was charged with 15.33 g (88 mmol) of 2,5-dimethyl-4methoxyphenylboronic acid, 16.18 g (80 mmol) of 1-bromo-2-nitrobenzene, 120 mL of toluene and 80 ml of K 2 CO 3 2M. The resulting solution was degassed with a vigorous flow of argon for 30 min, then 0.92 g (1 mol%, 0.8 mmol) of Pd(PPh 3 ) 4 was added under argon and the mixture was refluxed

Syntheses and properties of copolymers containing indolocarbazole moiety in the side chain

“…INC is known to show strong blue fluorescence under irradiation by ultraviolet (UV) light. In recent years, there have been some reports on the preparation and characterization of derivatives of INC. [16][17][18][19][20][21][22][23][24][25] In particular, Hu et al 21 have reported 1,7-dinaphtylindolo [3,2-b]carbazole, which showed excellent hole-transport properties in light-emitting diodes. Later, the first organic field-effect transistors using N-alkylated INC as an active layer was successfully fabricated.…”

“…Later, the first organic field-effect transistors using N-alkylated INC as an active layer was successfully fabricated. 16 In addition, there have also been some reports on polymers containing the INC moiety. [26][27][28][29] For example, Li et al 15 synthesized a new class of polyindolocarbazole via the coupling polymerization of 2,8-dichloroindolo [3,2-b]carbazole derivatives, a film of which could be manufactured by spin coating and exhibited a field-effect transistor mobility of 0.02 cm 2 V À1 s À1 .…”

1,4,9,12-Tetramethoxy-14-octyl-5,8-dihydrodiindolo[3,2-b;2′,3′-h]carbazole with an unknown solvent

“…Indolocarbazoles are currently investigated as materials for optical (Nemkovich et al, 2009) and electronic applications (Wakim et al, 2004;Zheng et al, 2015). Among the different synthetic routes (Vlasselaer & Dehaen, 2016), the twofold Cadogan reaction (Cadogan et al, 1965) is a very successful route to indolocarbazoles (Kistenmacher & Mü llen, 1992;Wrobel et al, 2013) and is also suitable for the preparation of higher oligomers (Srour et al, 2016).…”

Two isostructural halogen derivatives of 9-ethylcarbazole: crystal structure, Hirshfeld surface analysis, and structural comparison with other simple analogs

“…Namely, materials based on them are very promising because of their great stability, good solubility, excellent photoconductive properties, relatively intense luminescence, and good performance in OFETs, OLEDs, and thermoelectric materials [42][43][44][45][46][47][48][49][50][51][52]. Moreover, these compounds, and particularly halogenated carbazoles, are important synthetic intermediates and pharmacological targets [53].…”