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

• Mio Matsumura,
• Takahiro Teramoto,
• Masato Kawakubo,
• Masatoshi Kawahata,
• Yuki Murata,
• Kentaro Yamaguchi,
• Masanobu Uchiyama and
• Shuji Yasuike

Beilstein J. Org. Chem. 2021, 17, 671–677, doi:10.3762/bjoc.17.56

• 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. Keywords: benzo[f]naphtho[2,3-b]phosphoindole; molecular structure; optical

• phosphorus center can be easily chemically modified and converted to phosphole derivatives with different electronic properties by reactions such as oxidation, alkylation, and coordination to a Lewis acid [1][2][3][4][5][6][7][8]. Theoretically, pentacyclic benzonaphthophosphindole contains six structural

• and IR). All the corresponding aromatic proton and carbon atoms on the two naphthalene rings were equivalent in the 1H and 13C NMR spectra of phospholes. These results show that all phosphole derivatives had a symmetric structure in solution. The 31P NMR spectra of these show the typical low-field

Synthesis of triphenylene-fused phosphole oxides via C–H functionalizations

• Md. Shafiqur Rahman and
• Naohiko Yoshikai

Beilstein J. Org. Chem. 2020, 16, 524–529, doi:10.3762/bjoc.16.48

• -conjugated functional molecules [1][2][3][4][5][6][7][8][9]. Its inherently unique electronic structure, along with opportunities to modify the phosphorus center and the periphery by substitution or ring fusion, have stimulated chemists to explore a structurally diverse range of phosphole derivatives with

• ]phospholes [36][37][38][39][40], this three-component method guarantees a good regioselectivity for the formation of the desired 7-hydroxybenzo[b]phosphole derivatives. The triphenylene moiety was completed in the last step through a Scholl reaction. The synthesized triphenylene-fused phosphole oxides showed

• benzo[b]phospholes accessible by the three-component assembly hold promise for further explorations inot novel π-extended phosphole derivatives. Examples of functional molecules based on π-extended phospholes. ORTEP drawings of compound 8a (thermal ellipsoids set at 50% probability). a) top view; b

Synthesis and photophysical properties of novel benzophospholo[3,2-b]indole derivatives

• Mio Matsumura,
• Mizuki Yamada,
• Atsuya Muranaka,
• Misae Kanai,
• Naoki Kakusawa,
• Daisuke Hashizume,
• Masanobu Uchiyama and
• Shuji Yasuike

Beilstein J. Org. Chem. 2017, 13, 2304–2309, doi:10.3762/bjoc.13.226

• tetracyclic moieties are planar. The benzophosphole-fused indoles, such as phosphine oxide, phospholium salt, and borane complex, exhibited strong photoluminescence in dichloromethane (Φ = 67–75%). Keywords: benzophospholo[3,2-b]indole; DFT calculation; molecular structure; phosphole derivatives

• corresponding phosphole derivatives with different electronic properties [10][11][12][13][14][15][16][17]. Phosphole-based ladder-type π-conjugated heteroacenes were shown to exhibit a high charge mobility and/or fluorescence quantum yields [18][19][20][21][22][23][24]. For example, dibenzo-fused phospholo[3,2

• ]indoles were evaluated using UV absorption and fluorescence spectroscopy in CH2Cl2. The spectra are shown in Figure 3, and the photophysical data are shown in Table 2. The functionalized phosphole derivatives 4–8 showed absorption maxima (λabs) at 299–307 nm and a broad absorption at ≈355 nm. In contrast

Phosphinate-containing heterocycles: A mini-review

• Olivier Berger and
• Jean-Luc Montchamp

Beilstein J. Org. Chem. 2014, 10, 732–740, doi:10.3762/bjoc.10.67

• . Selected recent synthetic work by us and others is presented below. Review Phospholes Several compounds have been prepared in this series. Keglevich and coworkers realized the synthesis of phosphole derivatives 2a–f based on the McCormack reaction [10] followed by microwave-assisted esterification of the