Efficient Synthesis, Structural Characterization, and Optical Properties of 6H‐Dibenzo[b,h]carbazole and Its Derivatives

Matsumura, Mio; Kawahata, Masatoshi; Muranaka, Atsuya; Hiraiwa, Miyuki; Yamaguchi, Kentaro; Uchiyama, Masanobu; Yasuike, Shuji

doi:10.1002/ejoc.201900464

Cited by 6 publications

(3 citation statements)

References 22 publications

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“…The results revealed that the naphthalene and fused phosphole rings are almost coplanar (mean deviation = 0.030 Å). The angle between each naphthalene ring containing ten carbon atoms is 1.64°, which is smaller than that for group 15 analogs (i.e., N -phenyldibenzo[ b , h ]carbazole: 4.47° or 2.57° [ 22 ], for crystal data, see Figure S2, Supporting Information File 1 and Sb-phenyldinaphtho[2,3- b :2′,3′- d ]stibole: 8.05° [ 23 ]). The sum of the bond angles around the phosphorus atom is 295.99°, and hence the phosphorus atom is sp 3 -hybridized and has a trigonal pyramidal geometry.…”

Section: Resultsmentioning

confidence: 98%

Synthesis, structural characterization, and optical properties of benzo[f]naphtho[2,3-b]phosphoindoles

Matsumura¹,

Teramoto²,

Kawakubo³

et al. 2021

Beilstein J. Org. Chem.

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Phosphole-fused π-conjugated acenes have been attracting interest because of the attractive features of the phosphole moiety, such as fluorescence and chemically modifiable properties. Herein, 6-phenyl-6H-benzo[f]naphtho[2,3-b]phosphoindole was prepared by reacting dichlorophenylphosphine with a dilithium intermediate derived from 3,3′-dibromo-2,2′-binaphthyl. Various derivatives, such as a phospholium salt and a borane–phosphole complex with functional groups on the phosphorus atom were synthesized using the obtained phosphole as a common starting material. Single-crystal X-ray analysis of the parent benzo[f]naphtho[2,3-b]phosphoindole revealed that the pentacyclic ring is almost planar. Fluorescence spectroscopy data showed that the phosphole derivatives, such as phosphine oxide and the phospholium salt and borane complex exhibited photoluminescence in chloroform.

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Section: Resultsmentioning

confidence: 98%

Synthesis, structural characterization, and optical properties of benzo[f]naphtho[2,3-b]phosphoindoles

Matsumura¹,

Teramoto²,

Kawakubo³

et al. 2021

Beilstein J. Org. Chem.

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“…The structures and synthetic routes for the novel heteroacenes prepared in this study are shown in Scheme 1. The cyclization precursors, 2-bromo-3-(2-bromophenyl)naphthalene (1a) and 2,2 -dibromo-3,3 -binaphthyl (1b), were synthesized using a modification of a previously reported procedure [32] that involved the SuzukiMiyaura cross-coupling of 3-bromo-2-naphthylboronic acid with 2-bromoiodobenzene or 3-bromo-2-iodonaphthalene, respectively. Sequential treatment of dibromo compound 1a with n-butyllithium in dry tetrahydrofuran at −78 • C followed by dibromo(phenyl)stibane resulted in ring closure, giving the desired product 2 in 46% yield.…”

Section: Synthesismentioning

confidence: 99%

“…Known cyclization precursors 1b [32] and 1c [31] were prepared according to the reported procedures, and spectroscopic data are in accordance with the literature.…”

Section: General Informationmentioning

confidence: 99%

Synthesis, Structural Characterization, and Optical Properties of Benzene-Fused Tetracyclic and Pentacyclic Stiboles

et al. 2021

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The expectation that antimony (Sb) compounds should display phosphorescence emissions based on the “heavy element effect” prompted our interest in the introduction of antimony to a biaryl as the bridging atom in a fused heterole system. Herein, the synthesis, molecular structures, and optical properties of novel benzene-fused heteroacenes containing antimony or arsenic atoms are described. The stiboles and arsole were prepared by the condensation of dibromo(phenyl)stibane or dichloro(phenyl)arsine with dilithium intermediates derived from the corresponding dibromo compounds. Nuclear magnetic resonance (NMR) spectroscopy and X-ray crystal analysis revealed that the linear pentacyclic stibole was highly symmetric in both the solution and crystal states. In contrast, the curved pentacyclic stibole adopted a helical structure in solution, and surprisingly, only M helical molecules were crystallized from the racemate. All synthesized compounds produced very weak or no emissions at room temperature or in the solid state. In contrast, the linear penta- and tetracyclic stiboles exhibited clear phosphorescence emissions in the CHCl3 frozen matrix at 77 K under aerobic conditions.

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Pd‐Catalyzed Decarboxylative Cross‐Coupling of N‐Aryl Anthranilic Acids to Access Carbazoles: Gram Scale Total Synthesis of Anti‐ Cancer Drug Ellipticine

Nadella,

Dadinaboyina,

Kumar

et al. 2023

Asian J Org Chem

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An efficient and scalable Pd‐catalyzed decarboxylative cross‐coupling strategy for the synthesis of carbazoles has been developed by using N‐aryl anthranilic acids. By employing a well‐designed catalytic system, this protocol access diverse carbazole derivatives via a C‐C bond‐formation in one‐pot. The substituted carbazoles were obtained in good to excellent yields with high functional‐group tolerance. We have also demonstrated the gram‐scale synthesis of the anti‐cancer drug Ellipticine by utilizing this methodology. This concise and scalable total synthesis of ellipticine exemplifies the efficiency of our methodology in producing this significant anti‐cancer compound.

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Efficient Synthesis, Structural Characterization, and Optical Properties of 6H‐Dibenzo[b,h]carbazole and Its Derivatives

Cited by 6 publications

References 22 publications

Synthesis, structural characterization, and optical properties of benzo[f]naphtho[2,3-b]phosphoindoles

Synthesis, structural characterization, and optical properties of benzo[f]naphtho[2,3-b]phosphoindoles

Synthesis, Structural Characterization, and Optical Properties of Benzene-Fused Tetracyclic and Pentacyclic Stiboles

Pd‐Catalyzed Decarboxylative Cross‐Coupling of N‐Aryl Anthranilic Acids to Access Carbazoles: Gram Scale Total Synthesis of Anti‐ Cancer Drug Ellipticine

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