Synthesis, characterization, and electroluminescent properties of star shaped donor–acceptor dendrimers with carbazole dendrons as peripheral branches and heterotriangulene as central core

Selective Tuning of the HOMO–LUMO Gap of Carbazole‐Based Donor–Acceptor–Donor Compounds toward Different Emission Colors

“…From cyclic voltammetry measurements, compounds 1 and 2 were found to exhibit a single reversible oxidation process at 1.17 and 1.21 V vs. SCE, which could be assigned to simultaneous one-electron oxidation of the two carbazole units. [26] Such an outcome may be due to the noncoplanarity of the central anthracene with 9,10-substituents, which results in negligible electronic interactions between the carbazole units. [18] Similarly for compounds 3 and 4, there exists a single reversible oxidation process at 1.15 and 1.17 V vs. SCE, which could be also assigned to simultaneous one-electron oxidation of the two carbazole units.…”

Substituent effects in nitro derivatives of carbazoles investigated by comparison of low-temperature crystallographic studies with density functional theory (DFT) calculations

“…The compounds are also considered to be potential candidates for electronic applications, such as colour displays, organic semiconductors, lasers and solar cells, as they demonstrate electroactivity and luminescence (Friend et al, 1999;Zhang et al, 2004). In recent years, crosslinked polycarbazole materials have also been widely employed as electron donors in materials for organic light-emitting diodes (OLEDs) (Shirota & Kageyama, 2007;Tao et al, 2011;Yook & Lee, 2012;Zhang et al, 2009). Herein, we present the crystal and molecular structures of 9H-carbazole, (I), 1-nitro-9H-carbazole, (II), and 9-nitrocarbazole, (III), all at 100 K. The structure of (I) at room temperature has been reported previously by several authors (Lahiri, 1968;Clarke & Spink, 1969;Kurahashi et al, 1969) and at 168 K by Gerkin & Reppart (1986).…”

Two-level self-assembly from nanowires to microrods based on a heterotriangulene derivative

“…Compound 1 was synthesized by a palladium-catalyzed Sonogashira cross-coupling reaction [22] of core derivative 3 [19] with three equiv of 1-dodecyloxy-4-ethynylbenzene 2 [23] in 85% yield (Scheme 1). As expected, 1 was readily soluble in common organic solvents such as toluene, CH 2 Cl 2 , and THF.…”

“…The n-type semiconductors are indispensable for diodes and complementary circuits with high operation speed and low power consumption, but their development lags a lot in comparison to the more common p-type counterparts in organic electronics [18]. As a part of our efforts toward synthesizing new organic n-type materials, we have identified heterotriangulene A (Chart 1) as a promising candidate in our previous work [19]. The three carbonyl groups of A greatly reduce the electron density of the aromatic core, a feature that has been shown to effectively promote p-p interaction [20], which is important for the conduction of electrons in n-type materials.…”