Synthesis of π-conjugated polycyclic compounds by late-stage extrusion of chalcogen fragments

• Aissam Okba,
• Pablo Simón Marqués,
• Kyohei Matsuo,
• Naoki Aratani,
• Hiroko Yamada,
• Gwénaël Rapenne and
• Claire Kammerer

Beilstein J. Org. Chem. 2024, 20, 287–305, doi:10.3762/bjoc.20.30

• the “precursor approach”, a synthetic strategy has to be devised according to a multi-step route to prepare the soluble precursor, in turn specifically designed to deliver the target π-CPC after activation in situ. This is thus fundamentally different from the approach consisting in reacting a

• precursor, recovery of the target π-CPC is possible via a cheletropic decarbonylation step upon photolysis or thermolysis (Scheme 1, bottom right). This dual activation mode has led to the solid-state formation, on a preparative scale, of higher acenes up to nonacene [28][29][30][31][32][33] and

Aromatic systems with two and three pyridine-2,6-dicarbazolyl-3,5-dicarbonitrile fragments as electron-transporting organic semiconductors exhibiting long-lived emissions

• Karolis Leitonas,
• Brigita Vigante,
• Dmytro Volyniuk,
• Audrius Bucinskas,
• Pavels Dimitrijevs,
• Sindija Lapcinska,
• Pavel Arsenyan and
• Juozas Vidas Grazulevicius

Beilstein J. Org. Chem. 2023, 19, 1867–1880, doi:10.3762/bjoc.19.139

• emitter based on a pyridine-3,5-dicarbonitrile scaffold (to serve as an electron acceptor) directly linked to a carbazole moiety (to serve as an electron donor) was reported by the groups of Dong and Zhang in 2015 [4]. 2,6-Di(9H-carbazol-9-yl)-4-phenylpyridine-3,5-dicarbonitrile (CPC) showed an extremely

• small singlet–triplet splitting and a fair photoluminescence quantum yield (PLQY). The optimized organic light-emitting diode (OLED) based on 13 wt % CPC doped in 1,3-bis(9H-carbazol-9-yl)benzene (mCP) as host exhibited maximum current efficiency, power efficiency, and external quantum efficiency (EQE

• the photocatalytic production of H2 while the nanospheres produced hydrogen peroxide (H2O2). The introduction of the additional carbazolylphenyl moiety in the CPC molecule [4] allowed us to improve the EQEmax of an OLED to 25% [7]. In continuation of our studies in the field of the development of new

Heterogeneous photocatalysis in flow chemical reactors

• Christopher G. Thomson,
• Ai-Lan Lee and
• Filipe Vilela

Beilstein J. Org. Chem. 2020, 16, 1495–1549, doi:10.3762/bjoc.16.125

Adhesion, forces and the stability of interfaces

• Robin Guttmann,
• Johannes Hoja,
• Christoph Lechner,
• Reinhard J. Maurer and
• Alexander F. Sax

Beilstein J. Org. Chem. 2019, 15, 106–129, doi:10.3762/bjoc.15.12

Three new trixane glycosides obtained from the leaves of Jungia sellowii Less. using centrifugal partition chromatography

• Luíse Azevedo,
• Larissa Faqueti,
• Marina Kritsanida,
• Antonia Efstathiou,
• Despina Smirlis,
• Gilberto C. Franchi Jr,
• Grégory Genta-Jouve,
• Sylvie Michel,
• Louis P. Sandjo,
• Raphaël Grougnet and
• Maique W. Biavatti

Beilstein J. Org. Chem. 2016, 12, 674–683, doi:10.3762/bjoc.12.68

• partition and centrifugal partition chromatography. Thus, the crude extract of fresh leaves of J. sellowii was partitioned with hexane, dichloromethane, ethyl acetate and butanol, respectively. The butanol fraction was then subjected to a selected ternary system optimized for the CPC (centrifugal partition

• antiprotozoal activity. Liquid–liquid partition and CPC turned to be a versatile technique of glycoside purification which is environmentally friendly and requires a limited amount of organic solvents. Keywords: CPC; guaiane; Jungia; trixanolide; Introduction Jungia (Asteraceae) comprises shrubs, lianas and

• complexity, and frequently have more advantageous ADME/T properties [18]. Compared to other chromatographic methods, centrifugal partition chromatography (CPC) is compatible with green chemistry criteria since it does not use any polluting solid support such as silica. Moreover, it allows the complete

SF002-96-1, a new drimane sesquiterpene lactone from an Aspergillus species, inhibits survivin expression

• Silke Felix,
• Louis P. Sandjo,
• Till Opatz and
• Gerhard Erkel

Beilstein J. Org. Chem. 2013, 9, 2866–2876, doi:10.3762/bjoc.9.323

• controlling cell division. In normal differentiated tissues the expression of survivin is cell cycle-regulated with an expression maximum in G2/M phase [7]. During mitosis, survivin is associated in the chromosomal passenger complex (CPC), a multi-protein complex, including the proteins Aurora B kinase, inner

• centromere protein (INCENP) and Borealin/Dasra-B. In this complex, survivin promotes mitosis by mediating the segregation of sister chromatids, stabilization of microtubules in late mitosis and acting as an interphase between the centromere/central spindle and the CPC [8][9]. Furthermore, survivin shuttles

Chemistry in flow systems III

• Andreas Kirschning

Beilstein J. Org. Chem. 2013, 9, 1696–1697, doi:10.3762/bjoc.9.193

• Ehrfeld Mikrosystem BTS and by CPC (Cellular Process Chemistry Systems) are marvelous examples of these engineered driven achievements. In the late nineties, organic chemists from both industry and academia, which included our group, became involved in the use of microreactors and provided a myriad of

Substituent effect on the energy barrier for σ-bond formation from π-single-bonded species, singlet 2,2-dialkoxycyclopentane-1,3-diyls

• Jianhuai Ye,
• Yoshihisa Fujiwara and
• Manabu Abe

Beilstein J. Org. Chem. 2013, 9, 925–933, doi:10.3762/bjoc.9.106

• crystallographic analysis as well as by NOE measurements. The steady-state photolyses of AZc–g in benzene solution were performed with a Xenon lamp (500 W) through a Pyrex filter (hν > 300 nm). The ring-closed compounds CPc–g were quantitatively obtained in the denitrogenation reaction (Scheme 2). The quantum

• yields of the denitrogenation of AZc–g were determined to be ≈0.90 by comparison with those reported for similar azoalkanes [33]. The quantitative formation of CPc–g and the high quantum yield of the denitrogenation process suggest the clean generation of DRc–g in the photoirradiation reaction of AZc–g

• molecular oxygen (decay trace at 580 nm, Figure 2c); and (d) the activation parameters (Table 1) are similar to those for the decay process of DRa, in particular, the high (ca. 1012 s−1) pre-exponential Arrhenius factors (logA) are indicative of a spin-allowed reaction to the ring-closed products CPc–g [34

Surfactant catalyzed convenient and greener synthesis of tetrahydrobenzo[a]xanthene-11-ones at ambient temperature

• Pravin V. Shinde,
• Amol H. Kategaonkar,
• Bapurao B. Shingate and
• Murlidhar S. Shingare

Beilstein J. Org. Chem. 2011, 7, 53–58, doi:10.3762/bjoc.7.9

• cetyltrimethylammonium bromide (CTAB), methyltriphenylphosphonium bromide (MTPPB) and cetylpyridinium chloride (CPC) as well as an anionic surfactant, sodium dodecyl sulfate (SDS), were utilized at ambient temperature. From these preliminary studies, it was observed that the anionic surfactant SDS and cationic

• surfactants CPC and MTPPB gave the desired product albeit in low yields, i.e., 57%, 32% and 59% respectively (Table 1, entries 1–3). In contrast, the cationic surfactant CTAB accelerated the model reaction to afford the desired product in good 81% yield (Table 1, entry 4). From this, it was concluded that