Synthesis and Optical Properties of Axially Chiral Bibenzo[b]carbazole Derivatives

Abstract

Pure organic materials with the circularly polarized luminescence (CPL) property have attracted significant research interest over the past few decades. In this study, a series of axially chiral bibenzo­[b]­carbazole derivatives were synthesized by adopting palladium- and iridium-catalyzed direct C–H functionalization reactions as the key steps. These compounds exhibited CPL characteristics with considerably large dissymmetry factors up to 2.81 × 10–2 in the solid state, indicating the formation of well-ordered aggregates.

Iodine-Catalyzed Annulation Reaction of Ortho-Formylarylketones with Indoles: A General Strategy for the Synthesis of Indolylbenzo[b]carbazoles

“…3 Recently, transition-metalcatalyzed C−H functionalization reactions have been reported for the synthesis of bibenzo [b]carbazole derivatives. 4 Moreover, other metal-catalyzed strategies were also reported to access the benzo [b]carbazole derivatives. 5 In 2019, palladiumcatalyzed cascade annulation of 2-vinylbenzaldehydes with indoles was reported to give the substituted benzo [b]carbazole derivatives.…”

“…Synthesis of carbazole derivatives has attracted the attention of many researchers due to the importance of these compounds in medicinal and materials chemistry . Recently, transition-metal-catalyzed C–H functionalization reactions have been reported for the synthesis of bibenzo­[ b ]­carbazole derivatives . Moreover, other metal-catalyzed strategies were also reported to access the benzo­[ b ]­carbazole derivatives .…”

Synthesis and Characterizations of 5,5′‐Bibenzo[rst]pentaphene with Axial Chirality and Symmetry‐Breaking Charge Transfer

“…For examples, 5,5′‐bitetracene exhibits axially chiral properties along C5—C5′ bond and its enantiomers can be resolved by chiral high‐performance liquid chromatography (HPLC; Figure 1 ). [ 20 ] Heteroatom‐incorporated analogs, such as bibenzo[ b ]carbazole with anisotropy factors g abs on the order of 10 −4 to 10 −3[ 21 ] and bis(dibenzothiophene) [ 22 ] are also reported. Nevertheless, reported examples of such axially chiral biaryls based on extended PAHs, without the use of bulky substituents to prohibit the isomerization, are still limited, especially for PAHs with more than four benzene rings.…”

Effect of Oxidation on the Chiroptical Properties of Sulfur-Bridged Binaphthyl Dimers

“…Chiral lanthanide complexes currently possess the highest | g lum | values (1.38 being the highest value reported); , however, it is also desirable to simultaneously have high photoluminescence efficiency (Φ F ). Emissive chiral small organic molecules (SOMs), including those that possess axial, − planar, − and heliconical , chirality, generally have higher emission efficiency, − and facile structural modification through synthetic chemistry can be used to finely tune emission properties in SOMs. It is generally difficult to achieve high Φ F and g lum simultaneously as SOMs typically suffer from low g lum values (<10 –3 ).…”