Fig. 5: Modular access to functionalized carbazole atropisomers. | Nature Communications

Fig. 5: Modular access to functionalized carbazole atropisomers.

From: Enantiotopic-group-selective coupling for unified access to carbazole atropisomers as versatile chiral chromophores

Fig. 5

A Synthesis of 3,6-disubstituted carbazoles. B Sequential coupling of trichloro N-aryl-carbazole. C Tactic conjugated oligomer. D 24-Membered chiral macrocycle. E Curtius rearrangement to amino compounds. F Access to new CP-TADF materials. G Synthesis of 2,7-disubstituted carbazoles through desymmetrization of 2,7-dibromocarbazole 80. aMn, Mw, and PDI were determined by gel permeation chromatography (GPC). Ac: acetyl; dan: naphthalene-1,8-diaminato; DIBAL-H: diisobutylaluminum hydride; DIPEA: N,N-diisopropylethylamine; EDC: N-(3-dimethylaminopropyl)-N’-ethylcarbodiimide; HOBt: 1-hydroxybenzotriazole; pin: pinacolato; SPhos: 2-dicyclohexylphosphino-2’,6’-dimethoxybiphenyl; TFA: trifluoroacetic acid; XPhos: 2-dicyclohexylphosphino-2’,4’,6’-triisopropylbiphenyl.

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