Chiral phosphoric acid-catalyzed asymmetric synthesis of helically chiral, planarly chiral and inherently chiral molecules

• Wei Liu and
• Xiaoyu Yang

Beilstein J. Org. Chem. 2025, 21, 1864–1889, doi:10.3762/bjoc.21.145

• good yield and excellent enantioselectivity (Scheme 5). Notably, two distinct oxidative aromatization methods have been developed to yield diverse heterohelicene products. For instance, using DDQ as an oxidant selectively delivered hetero[7]helicenes 19 with monoamido substitution at the peri-positions

Synthesis of an aza[5]helicene-incorporated macrocyclic heteroarene via oxidation of an o-phenylene-pyrrole-thiophene icosamer

• Yusuke Matsuo,
• Aoi Nakagawa,
• Shu Seki and
• Takayuki Tanaka

Beilstein J. Org. Chem. 2025, 21, 1561–1567, doi:10.3762/bjoc.21.119

• in detail. Keywords: cyclophane; fluorescence; heterohelicene; intramolecular oxidative coupling; Introduction Conjugated macrocyclic polyarenes have attracted significant attention due to their stimuli-responsive optoelectronic properties, dynamic structural changes, and host–guest interactions [1

• largest macrocycle ever synthesized is a dodecameric hybrid array of 1,2-phenylene, 2,5-thienylene, and 2,5-pyrrolylene units [22][23]. The intramolecular oxidative coupling of these arrays afforded heterohelicene-incorporated macrocycles D and E, depending on the relative arrangements of the pyrrole and

Advances in nitrogen-containing helicenes: synthesis, chiroptical properties, and optoelectronic applications

• Meng Qiu,
• Jing Du,
• Nai-Te Yao,
• Xin-Yue Wang and
• Han-Yuan Gong

Beilstein J. Org. Chem. 2025, 21, 1422–1453, doi:10.3762/bjoc.21.106

• seconds. In contrast, 4b exhibits superior chiroptical properties, with |gabs| and |glum| values of 3.91 × 10−3 and 1.12 × 10−3, respectively, and an impressive BCPL of 45.77 M−1 cm−1 (Table 1). In 2021, several research groups reported structurally diverse heterohelicene systems exhibiting distinctive

• chiral luminophores with reversible CPL modulation, offering promising strategies for the development of advanced molecular optoelectronic devices. In 2021, Hatakeyama and co-workers developed an expanded B,N-containing heterohelicene 37 via a one-step synthesis employing excess BBr3 at 180 °C in an

• (MR-TADF) emitters to date. In 2023, the same group introduced the first deep-blue chiral MR-TADF emitters based on heterohelicene scaffolds 41a–c [56]. These compounds exhibited sharp emissions at 440–444 nm in solution and 445–449 nm in doped films, with emission bandwidths as narrow as 23 nm and

The efficient synthesis of dibenzo[d,d′]benzo[1,2-b:4,3-b′]dithiophene and cyclopenta[1,2-b:4,3-b′]bis(benzo[d]thiophen)-6-one

• Zhihua Wang,
• Sheng Zhu,
• Jianwu Shi and
• Hua Wang

Beilstein J. Org. Chem. 2009, 5, No. 55, doi:10.3762/bjoc.5.55

• ] as starting material, dibenzo[d,d′]benzo[1,2-b:4,3-b′]dithiophene, a [5]heterohelicene, was synthesized efficiently in 60% yield via formylation and McMurry reaction. Cyclopenta[1,2-b:4,3-b′]bis(benzo[d]thiophen)-6-one, another interesting helical ketone, was also prepared in 79% yield via

• (1), an interesting [5]heterohelicene, has not received much attention during the last decade because of a lack of efficient synthesis, which limits its application in material science. Photocyclization is normally employed for preparing heterohelicenes with 1,2-diaryl ethenes as precursors. Wynberg