Synthesis, Structure, and Physical Properties of 5,7,14,16‐Tetraphenyl‐8:9,12:13‐bisbenzo‐hexatwistacene

Abstract

A novel compound, 5,7,14,16-tetraphenyl-8:9,12:13-bisbenzo-hexatwistacene (TBH), has been successfully synthesized through a retro-Diels-Alder reaction. Single-crystal structure analysis indicated that TBH has a twisted configuration with a torsion angle of 27.34°. The HOMO-LUMO gap of TBH calculated from the difference between the half-wave redox potentials (E(1/2) (ox) =+0.40 eV and E(1/2)(red) =-1.78 eV) is 2.18 eV, which is in good agreement with the band gap (2.19 eV) derived from the UV/Vis absorption data. In addition, organic light-emitting devices using TBH as emitter have been fabricated. The results revealed that TBH is a promising red light-emitting candidate for applications in organic light-emitting diodes.

Virtually pure near-infrared electroluminescence from exciplexes at polyfluorene/hexaazatrinaphthylene interfaces

“…10 Recently, some of us have reported a successful strategy to twist the otherwise planar structure of HATNA by introducing bulky silyl groups in confronting positions and to influence their properties by means of such distortions. 11 Distorted polycyclic aromatic hydrocarbons [12][13][14][15][16][17] have emerged as promising materials for OLED applications [18][19][20][21][22] since the twisted conformation substantially reduces intermolecular p-p interactions, leading to enhanced solubility and to a reduction of aggregation-induced quenching in the solid state.…”

Self-assembled multicolor nanoparticles based on functionalized twistacene dendrimer for cell fluorescent imaging

“…In the molecular structure, the terminal pyrene unit is almost coplanar, and the near naphthalene moiety is twisted out of this plane, which was similar to our reported molecules. [35][36][37][38][39][40] It should be noted that the twisted torsion angle of plane C1-C2-C24 and plane C10-C12-C14 is 27.69°. Furthermore, the intermolecular distance is more than 3.8 Å, inferring that π-π stacking interaction is absent between intermolecules based on the packing model (Figure 2b).…”

“…[32][33][34] Wudl, Zhang and Xiao synthesized a series of symmetric and asymmetric twistacenes containing primary color luminescence from blue to green and red through retro-Dies-Alder reaction. [35][36][37][38][39][40] It is well known that well-defined conjugated dendrimers having branched and regularly repeating molecular units possess many advantages over small molecules and the hyperbranched polymers. The optoelectronic properties of these dendrimers can be finely tuned by changing the core, decorating with various surface groups and grafting with different functional generations.…”

Aryne Cycloaddition Reactions in the Synthesis of Large Polycyclic Aromatic Compounds

“…Zhang and Wudl and their co‐workers have recently reported the synthesis of benzoannulated hexacene 206 ,95 heptacene 207 96 and nonacene 208 97 with eight, nine and thirteen fused benzene rings, respectively, by a retro‐Diels–Alder process involving the thermal elimination of lactam bridges from soluble acene precursors (Figure 7).…”