An alternative approach to triazatruxene synthesis and derivatization to a boron difluoride complex

Abstract

The extensively studied organic material 5,10,15-triazatruxene is usually synthesized by the trimerization of indole or 2-indolone using the toxic liquid bromine and phosphoryl chloride. Herein we report an efficient synthetic...

A series of boron difluoride complexes of azinylcarbazoles: synthesis and structure–property relationships

“…After this report, several carbazole-based BF 2 complexes have been developed. [7][8][9][10][11][12][13][14][15][16][17][18][19][20][21] Especially, Maeda and Ema et al have systematically synthesized carbazole-based BF 2 complexes bearing a pyrrolic heterocycle 10 or an aryl imine moiety 19 at the 1-position of the carbazole and revealed the relationships between their structures and properties. In addition, several groups have developed π-extended carbazole BF 2 complexes 9,16,18 and dimeric complexes.…”

Triple B←N Lewis Pair-Functionalized Triazatruxenes with Large Stokes Shifts

“…40−42 There have been few reports on the functionalization of TAT at positions 1, 6, and 11 due to the scarcity of appropriate methods for introducing functional groups at these positions. 43 Zhang and co-workers utilized iridium-catalyzed borylation to introduce -Bpin groups at positions 1, 6, and 11 of TAT and then functionalized it by further means of the palladium-catalyzed Suzuki−Miyaura cross-coupling reaction. 43 Saracoglu's group realized the triarylation of the nonperipheral positions in a TAT scaffold for the first time via two approaches that involve arylation/cyclotrimerization and cyclotrimerization/arylation sequences.…”

“…43 Zhang and co-workers utilized iridium-catalyzed borylation to introduce -Bpin groups at positions 1, 6, and 11 of TAT and then functionalized it by further means of the palladium-catalyzed Suzuki−Miyaura cross-coupling reaction. 43 Saracoglu's group realized the triarylation of the nonperipheral positions in a TAT scaffold for the first time via two approaches that involve arylation/cyclotrimerization and cyclotrimerization/arylation sequences. 44 However, these methods usually require multiple steps.…”

“…C 3 symmetric, planar triazatruxene (TAT) has been extensively studied because of its structure unity, multiple modifiable sites, ease of synthesis, and electron-rich structure and possesses high electrical conductivity and electron-donating and hole-transporting capabilities, showing high performance in two-photon absorption (TPA), organic light-emitting diodes (OLEDs), organic photovoltaics (OPVs), , liquid crystal displays (LCDs), and organic lasers . There are 15 available positions in TAT, and alkyl chains are usually attached to nitrogen atoms in pentagonal rings (positions 5, 10, and 15) to enhance solubility and inhibit π–π stacking; on the contrary, peripheral positions (2, 3, 7, 8, 12, and 13) are easily modified with aryl and other conjugated groups to obtain compounds with different properties (Figure b). − There have been few reports on the functionalization of TAT at positions 1, 6, and 11 due to the scarcity of appropriate methods for introducing functional groups at these positions . Zhang and co-workers utilized iridium-catalyzed borylation to introduce -Bpin groups at positions 1, 6, and 11 of TAT and then functionalized it by further means of the palladium-catalyzed Suzuki–Miyaura cross-coupling reaction .…”

“…There are 15 available positions in TAT, and alkyl chains are usually attached to nitrogen atoms in pentagonal rings (positions 5, 10, and 15) to enhance solubility and inhibit π–π stacking; on the contrary, peripheral positions (2, 3, 7, 8, 12, and 13) are easily modified with aryl and other conjugated groups to obtain compounds with different properties (Figure b). − There have been few reports on the functionalization of TAT at positions 1, 6, and 11 due to the scarcity of appropriate methods for introducing functional groups at these positions . Zhang and co-workers utilized iridium-catalyzed borylation to introduce -Bpin groups at positions 1, 6, and 11 of TAT and then functionalized it by further means of the palladium-catalyzed Suzuki–Miyaura cross-coupling reaction . Saracoglu’s group realized the triarylation of the nonperipheral positions in a TAT scaffold for the first time via two approaches that involve arylation/cyclotrimerization and cyclotrimerization/arylation sequences .…”