Polybrominated anthracenes: selective synthesis of tetrabromoanthracenes as precursors for the corresponding tetracyanoanthracenes

Extending the Scope of a New Cyanation: Design and Synthesis of an Anthracene Derivative with an Exceptionally Low LUMO Level and Improved Solubility

“…The suspension was then filtered, and 1.5 mL of the resulting solution was used to determine the dissolved amount of 2 by evaporation of the solvent. NMR spectra were recorded at 600 MHz for 1 H and 150 MHz for 13 C on a Bruker Avance III HD spectrometer and at 400 MHz for 1 H on a Bruker Avance DRX-400 spectrometer. Data for 1 H NMR are reported as follows: chemical shift in parts per million (ppm) from tetramethylsilane (TMS) using the residual solvent signal as an internal reference (CDCl 3 : δ = 7.26 ppm, DMSOd 6 : δ = 2.50 ppm), multiplicity (s = singlet, d = doublet, dd = doublet of doublets), and integration.…”

“…Data for 1 H NMR are reported as follows: chemical shift in parts per million (ppm) from tetramethylsilane (TMS) using the residual solvent signal as an internal reference (CDCl 3 : δ = 7.26 ppm, DMSOd 6 : δ = 2.50 ppm), multiplicity (s = singlet, d = doublet, dd = doublet of doublets), and integration. 13 C NMR data are reported in ppm from TMS using the central peak of the solvent as reference (CDCl 3 : δ = 77.16 ppm, DMSO-d 6 : δ = 39.52 ppm); the multiplicity with respect to H (s = quaternary C, d = CH) is deduced from APT experiments. HPLC measurements were carried out on a system of Agilent Technologies (1200 Series G1367B HiP ALS Autosampler, 1100 Series G1311A Quat Pump, 1100 Series G1379A Degasser, 1200 Series G1316B TCCSL, 1260 Infinity G1315D DAD).…”

“…Attaching two additional cyano groups to the well-investigated 9,10-dicyanoanthracene (DCA) may appear as a reasonable approach; a straightforward synthesis of such tetracyanoanthracenes has been reported. 13 However, these compounds do not exhibit satisfying solubility despite the smaller aromatic π-system. Attaching alkylated electron-withdrawing groups, such as imides, improves the solubility, 14 but the insulating alkyl chains can deteriorate the charge transport properties.…”

“…NMR). Characterization data of 4: 1 H NMR (600 MHz, CDCl 3 , δ): 9.67 (d, J = 2.1 Hz, 2H), 8.69 (d, J = 9.4 Hz, 2H), 8.60 (dd, J = 9.4, 2.1 Hz, 2H) ppm;13 C NMR (150 MHz, CDCl 3 , δ): 147.7 (s), 136.6 (s), 136.0 (s), 130.2 (s), 128.9 (d), 126.6 (d), 124.2 (d), 115.4 (s), 108.3 (s) ppm. λ max (ε) = 260 (41 000), 315 (37 000), 405 nm (5000 M −1 cm −1 ).…”

Facile Synthesis of Cyanoarenes from Quinones by Reductive ­Aromatization of Cyanohydrin Intermediates

“…Using quinones as reactants en-ables the preparation of many compounds from available substrates; on the other hand, it allows for substitution patterns that are difficult to realize using alternative methods. 5 Unlike lithium acetylides, cyanides favor 1,4-addition to benzoquinones over 1,2-addition. This problem can be overcome by the application of trimethylsilyl cyanide (TMSCN) for the synthesis of stable (silylated) cyanohydrins.…”