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Search for "carbazole" in Full Text gives 102 result(s) in Beilstein Journal of Organic Chemistry.
On the photoluminescence in triarylmethyl-centered mono-, di-, and multiradicals
Beilstein J. Org. Chem. 2025, 21, 964–998, doi:10.3762/bjoc.21.80
- the hole will reside on the mesityl and phenyl units (HDMO) and the electron resides on the PyBTM core (SOMO) (see Figure 4b). Instead of pyridine also carbazole (Cz) units have been coupled to produce N-carbazolyl-bis(2,4,6-trichlorophenyl)methyl radicals (CzBTM) (see Figure 5a). ϕ is highest at λem
- compounds. Breaking of the symmetry for the |D1⟩ transition by incorporating a donor moiety, leads to enhanced intensity as reflected by growing absorption coefficients ε with increasing donor strength (see Table 1). Replacing one of the phenyl rings for carbazole in triarylmethyl radical leads to much
- chemical investigations have also brought forth that the dihedral angle between the TTM radical plane and the carbazole donor increases when exciting the molecule from the D0 ground state to the excited D1 state. In the D1 state the Cz is aligned almost perpendicular to the TTM plane, which will stabilize
Study of tribenzo[b,d,f]azepine as donor in D–A photocatalysts
Beilstein J. Org. Chem. 2025, 21, 935–944, doi:10.3762/bjoc.21.76
- offers unique features, including twisted structures, reduced π–π stacking, and enhanced reverse intersystem crossing rates, becoming a better donor compared to fully planar compounds as carbazole (c). Similarly, 5H-dibenz[b,f]azepine (IMD, b) has been incorporated into D–A–D structures, showing
- . Additionally, we aim to evaluate the unique effect of the TBA donor unit (a) compared to other donors. We next synthesized diverse D–A structures employing common nitrogen-based compounds widely used in materials chemistry like carbazole (c), diphenylamine (d), and phenoxazine (e). Furthermore, we wanted to
Recent advances in the electrochemical synthesis of organophosphorus compounds
Beilstein J. Org. Chem. 2025, 21, 770–797, doi:10.3762/bjoc.21.61
- decomposition leads to the generation of O₂, the primary oxygen source in the reaction process. A radical process was proposed in the reaction. Diphenylphosphine oxide and carbazole radicals were formed via anodic oxidation in the presence of a base, followed by a coupling reaction to give the final P–N product
- -withdrawing groups such as –Cl, –Br, and –CO2Me. It was observed that carbazole derivatives with an extended conjugated system showed enhanced reactivity. Like the above P–N coupling mechanism, the reaction proceeded by an anodic oxidation of iodide to iodine followed by a reaction with dialkylphosphine oxide
- to give I–P(O)(R)2. The exact mechanism of this coupling reaction is not yet fully understood; however, the possibility of direct radical cross-coupling between the nitrogen radical derived from carbazole and the phosphoryl radical intermediate cannot be completely ruled out. In another
Red light excitation: illuminating photocatalysis in a new spectrum
Beilstein J. Org. Chem. 2025, 21, 296–326, doi:10.3762/bjoc.21.22
- have been calculated and have indicated that this latter could be a viable candidate for use in photoredox catalysis. Additionally, its measured excited-state lifetime (τ = 5.5 ns) is similar to those of other widely used organic photocatalysts, such as carbazole derivatives, further supporting its
Recent advances in organocatalytic atroposelective reactions
Beilstein J. Org. Chem. 2025, 21, 55–121, doi:10.3762/bjoc.21.6
- carbazole 223 or indole 225. The reactions provided excellent enantioselectivities and good yields and the best results were achieved with methyl or chlorine substituents in position 3 of the naphthyl ring. Dicarbazoles are generally useful as OLED materials [97]. For this reason, the authors decided to
Synthesis, characterization, and photophysical properties of novel 9‑phenyl-9-phosphafluorene oxide derivatives
Beilstein J. Org. Chem. 2024, 20, 3299–3305, doi:10.3762/bjoc.20.274
- studies, revealing that their photophysical behavior can be affected by the different substituents in the donor carbazole group. Keywords: carbazole; D−A−D type; noble-metal-free system; 9‑phenyl-9-phosphafluorene oxide; photophysical properties; Introduction π-Conjugated molecular materials containing
- acceptor group in TADF emitters, indicating great potential for the development of highly efficient TADF molecules. In 2019, Nishida and co-workers prepared 5 D–A–D-type PhFlOP derivatives with electron-donating diarylamine or carbazole moieties in positions 2 and 8. They conducted optical and
- access to PhFlOP-based TADF emitters. Additionally, the design of TADF emitters with the PhFlOP acceptor moiety and the carbazole donor moiety is lacking structural diversity. Herein, we present a 5-step synthesis of several novel D−A−D-type PhFlOP derivatives with substituted carbazole groups as donors
Applications of microscopy and small angle scattering techniques for the characterisation of supramolecular gels
Beilstein J. Org. Chem. 2024, 20, 2608–2634, doi:10.3762/bjoc.20.220
- -assembly across length scales using a combination of SANS and cryo-TEM, as well as other characterisation techniques. To investigate how the change in capping group changed the self-assembly of diphenylalanine, indole-FF, and carbazole-FF (F = phenylalanine) were characterised by SAXS. While both indole-FF
- and carbazole-FF were shown to have fibre radii that were quantifiable by SAXS, the model fit to the indole-FF showed the length to exceed the q range measured. Cryo-TEM was used to corroborate the presence of such fibres, and though they cannot prove the modelled length’s accuracy, they were able to
Diameter-selective extraction of single-walled carbon nanotubes by interlocking with Cu-tethered square nanobrackets
Beilstein J. Org. Chem. 2024, 20, 1298–1307, doi:10.3762/bjoc.20.113
- steric hindrance along the pyrene–carbazole bond than that along the anthracene–carbazole one. To predict the appropriate diameters of SWNTs, the spherical cavity sizes were calculated by considering van der Waals radii of all the atoms. The cavity size of Cu-nanobrackets 1b (11.83 Å) is 2.09 Å larger
Perspectives on push–pull chromophores derived from click-type [2 + 2] cycloaddition–retroelectrocyclization reactions of electron-rich alkynes and electron-deficient alkenes
Beilstein J. Org. Chem. 2024, 20, 125–154, doi:10.3762/bjoc.20.13
Synthesis of N-acyl carbazoles, phenoxazines and acridines from cyclic diaryliodonium salts
Beilstein J. Org. Chem. 2024, 20, 12–16, doi:10.3762/bjoc.20.2
- fluorophors, previously shown to exhibit strong organic phosphorescence when mixed with specific additives [1][2][3][4][5]. Carbazole units are also found in drugs and natural products. They are also used in electrochemistry and as reagents in transamidation reactions [6][7][8][9][10][11][12]. The traditional
- method to produce this versatile N-acyl carbazole motif involves combining 9H-carbazoles with acyl chlorides or similar activated acyl derivatives in the presence of a base (Scheme 1a) [13][14]. As an alternative, acyl carbazoles can be synthesized through step-wise metal-catalysed C–X-amidations
- [33][34]. Results and Discussion Initially, we investigated the synthesis of N-acyl carbazole by treatment of diaryliodonium salt 1a with valeramide using Cu(I) catalysts [18]. The results are shown in Table 1. In the first experiments in p-xylene at 120 °C with DMEDA as N,N-ligand, only modest
Aromatic systems with two and three pyridine-2,6-dicarbazolyl-3,5-dicarbonitrile fragments as electron-transporting organic semiconductors exhibiting long-lived emissions
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
- )-4-(4-bromophenyl)pyridine-3,5-carbonitrile (4) was obtained by the interaction of 3,6-di-tert-butyl-9H-carbazole with compound 3 in THF/DMF solution. The ethynylphenyl-substituted pyridine 5 was synthesized by Sonogashira coupling of 4 with ethynyltrimethylsilane in the presence of PdCl2(PPh3)2 and
- transfer from the donor to the acceptor. The absorption spectrum of REF is included in Figure 2a for comparison. Compounds 6–9 are characterized by similar absorption bands also caused by electron transfer from the 3,6-di-tert-butyl-9H-carbazole units to the pyridine-3,5-dicarbonitrile moiety. The number
Thienothiophene-based organic light-emitting diode: synthesis, photophysical properties and application
Beilstein J. Org. Chem. 2023, 19, 1849–1857, doi:10.3762/bjoc.19.137
- layers are composed of various aromatic π-conjugated small molecules/polymers including thiophene, anthracene, carbazole, and triphenylamine [9][10][11][12][13]. Thienothiophenes are two annulated thiophene rings having four isomers, among which the most widely used isomer is thieno[3,2-b]thiophene (TT
N-Boc-α-diazo glutarimide as efficient reagent for assembling N-heterocycle-glutarimide diads via Rh(II)-catalyzed N–H insertion reaction
Beilstein J. Org. Chem. 2023, 19, 1841–1848, doi:10.3762/bjoc.19.136
- pyrazole derivatives (including indazole), benzimidazole, 1,2,3-triazole, indole, carbazole, indoline, quinazoline, and isoquinoline. Nevertheless, many heterocyclic motifs still remain beyond the attention of researchers. For example, glutarimides that incorporate tetrazole and 1,2,4-triazole substituents
A deep-red fluorophore based on naphthothiadiazole as emitter with hybridized local and charge transfer and ambipolar transporting properties for electroluminescent devices
Beilstein J. Org. Chem. 2023, 19, 1664–1676, doi:10.3762/bjoc.19.122
- –donor (D–A–D)-type molecule and its application as a non-doped emitter in an organic light-emitting diode (OLED). The fluorophore TPECNz contains naphtho[2,3-c][1,2,5]thiadiazole (Nz) as a strong acceptor unit symmetrically functionalized with N-(4-(1,2,2-triphenylvinyl)phenyl)carbazole as a donor and
- twist angle between the D and A units, a strong electron deficiency of the Nz unit, and electron-donating and hole-transporting natures of carbazole, TPECNz exhibits a strong deep red emission (λem = 648 nm) with a high fluorescence quantum yield of 96%, outstanding thermal property (Tg = 236 °C), and
- energy gap between HOMO/LUMO hybrid orbits and drive fluorescence emission to longer wavelengths [48][49]. In this molecular design, the strong electron-deficient naphtho[2,3-c][1,2,5]thiadiazole (Nz) [13][50][51] as an acceptor and the strong electron-donating carbazole [52] as a donor unit were used in
Organic thermally activated delayed fluorescence material with strained benzoguanidine donor
Beilstein J. Org. Chem. 2023, 19, 1289–1298, doi:10.3762/bjoc.19.95
- benzoguanidine donor and compare it with the benchmark carbazole-based material (4CzIPN). Extended π-conjugation in 4BGIPN material results in yellow-green luminescence at 512 nm with a fast radiative rate of 5.5 × 10−5 s−1 and a photoluminescence quantum yield of 46% in methylcyclohexane solution. Such a
- performance in OLED devices [1]. 4CzIPN is a donor–acceptor-type system where carbazole donor ligands are bound to the benzonitrile acceptor core moiety. In this work we have substituted the carbazole donors with 5H-benzo[d]benzo[4,5]imidazo[1,2-a]imidazole (benzoguanidine) ligands to give 4BGIPN, see Figure
- 1. Benzoguanidine has an extended π-conjugation compared with carbazole and is more nitrogen-rich (three N-atoms vs one in carbazole). Thompson et al. recently reported a series of carbene–metal–amide (CMA) (metal = Cu, Ag, Au) emitters employing a benzoguanidine ligand [10]. The extended π
Enabling artificial photosynthesis systems with molecular recycling: A review of photo- and electrochemical methods for regenerating organic sacrificial electron donors
Beilstein J. Org. Chem. 2023, 19, 1198–1215, doi:10.3762/bjoc.19.88
- example could not be found where it was used in artificial photosynthesis or RFB research. The carbazole 9-ethyldodecahydro-1H-carbazole (DEC-H12) has an oxidation potential of 0.57 vs Fc/Fc+ and can carry 6 hydrogen equivalents [74] (DEC-H12 has been classified as an amine in Figure 5). The oxidation
- carbazole heterocyclic oxidation products [75]. LOHC compounds could potentially provide both protons and electrons for artificial photosynthesis. The thermodynamics of electrochemically hydrogenating several LOHCs using a modified water-splitting device have been investigated [40]. However, other
Photoredox catalysis harvesting multiple photon or electrochemical energies
Beilstein J. Org. Chem. 2023, 19, 1055–1145, doi:10.3762/bjoc.19.81
The effect of dark states on the intersystem crossing and thermally activated delayed fluorescence of naphthalimide-phenothiazine dyads
Beilstein J. Org. Chem. 2023, 19, 1028–1046, doi:10.3762/bjoc.19.79
- electron donor for the construction of electron donor–acceptor TADF molecules is carbazole. However, since our aim was to study the TADF photophysics with model TADF emitters, the use of phenothiazine (PTZ) instead of carbazole presents a few advantages. First, upon connection of the electron acceptor (i.e
- ., the NI unit) to the N atom of phenothiazine, a more restricted geometry is achieved than using carbazole. This is beneficial for the orthogonal geometry and thus TADF is ensured. Second, as compared with carbazole, the use of phenothiazine in the construction of TADF emitters offers an additional
Clauson–Kaas pyrrole synthesis using diverse catalysts: a transition from conventional to greener approach
Beilstein J. Org. Chem. 2023, 19, 928–955, doi:10.3762/bjoc.19.71
- solvent at 100 °C (Scheme 6). Finally, compounds 13 were used to prepare various arylpyrrolo- and pyrazolopyrrolizinones for diverse biological activity. In 2007, Török and co-workers [60] reported a convenient one-pot synthesis of N-sulfonyl-substituted pyrroles, indoles, and carbazole via a modified
Strategies in the synthesis of dibenzo[b,f]heteropines
Beilstein J. Org. Chem. 2023, 19, 700–718, doi:10.3762/bjoc.19.51
- of an N-triarylated dibenzo[b,f]azepine scaffold 129 by means of Au(I)-catalysed hydroarylation was reported by Ito et al. [70]. While the attempted synthesis of an N-phenyldibenzazepine derivative 127 was unsuccessful, the authors were able to prepare a fused carbazole-dibenzo[b,f]azepine 129 in 90
- metathesis as key step in the synthesis of dibenzo[b,f]heteropines. Alkyne–aldehyde metathesis in the synthesis of dibenzo[b,f]heteropines. Hydroarylation of 9-(2-alkynylphenyl)-9H-carbazole derivatives. Oxidative coupling of bisphonium ylide intermediate to give pacharin (13). Preparation of 10,11
Ionic multiresonant thermally activated delayed fluorescence emitters for light emitting electrochemical cells
Beilstein J. Org. Chem. 2022, 18, 1311–1321, doi:10.3762/bjoc.18.136
- a green EL with a peak brightness of 572 cd m−2 and an EQEmax of 6.8% at 4.0 V. The half-life of their device reached 218 h at a brightness of 162 cd m−2. Recently, Su et al. reported two ionic TADF emitters incorporating a pyridinium moiety, Pym-CZ and Pym-tBuCZ as the acceptor and carbazole or
Thermally activated delayed fluorescence (TADF) emitters: sensing and boosting spin-flipping by aggregation
Beilstein J. Org. Chem. 2022, 18, 1177–1187, doi:10.3762/bjoc.18.122
- the aggregated state have not yet been performed [28]. The acceptor core BPy, coupled with carbazole derivatives, produced BPy-pTC and BPy-p3C, respectively (Scheme 1). The detailed synthetic procedures and characterization data are given in the Experimental section and in Schemes S1 and S2 in
Heterogeneous metallaphotoredox catalysis in a continuous-flow packed-bed reactor
Beilstein J. Org. Chem. 2022, 18, 1123–1130, doi:10.3762/bjoc.18.115
- nickel catalyst in a single material have been reported [23][25][26][27]. For example, some of us have shown that a bipyridine ligand decorated with two carbazole groups can be polymerized to afford a heterogeneous macroligand (poly-czbpy) that coordinates nickel and serves as an active catalyst for
- metallaphotoredox catalysis in continuous flow. The heterogeneous catalyst used, based on a bipyridine ligand decorated with two carbazole groups, served as both photo- and nickel catalyst, making the reactor packing simple and reproducible. Compared with homogeneous approaches to metallaphotoredox catalysis, this
Synthesis, optical and electrochemical properties of (D–π)2-type and (D–π)2Ph-type fluorescent dyes
Beilstein J. Org. Chem. 2022, 18, 1047–1054, doi:10.3762/bjoc.18.106
- with two (diphenylamino)carbazole-thiophene units as D (electron-donating group)–π (π-conjugated bridge) moiety and the (D–π)2Ph-type fluorescent dye OTK-2 with the two D–π moieties connected through a phenyl ring were derived by oxidative homocoupling of a stannyl D–π unit and Stille coupling of a
- dyes [10][11][12][13][21][22][27][28][32]. In our previous work [33], we have reported the synthesis, optical and electrochemical properties of the (D–π)2Ph-type fluorescent dye OTK-2 with two (diphenylamino)carbazole-thiophene units as D–π moiety connected through a phenyl ring (Scheme 1). The ICT
- orbital (MO) calculations. Results and Discussion Using a toluene solution containing 1,3-diiodobenzene and (diphenylamino)carbazole-thiophenestannane derivative 1 [33] in the presence of Pd(PPh3)4, the (D–π)2-type and (D–π)2Ph-type fluorescent dyes OTK-2 [33] and OTT-2 were obtained by Stille coupling of
Post-synthesis from Lewis acid–base interaction: an alternative way to generate light and harvest triplet excitons
Beilstein J. Org. Chem. 2022, 18, 825–836, doi:10.3762/bjoc.18.83
- 7 in Figure 5), which consisted of the twisted A–π–D–π–A structure with N-(4-aminophenyl)carbazole (CzPA) as electron donor unit, pyridine as electron acceptor unit, and 9,9-dioctylfluorene (F) as π-conjugated linker [32]. Compound 7 showed remarkable dual-fluorescence properties when mixed with a
- fluorene showed enhanced planarity of the molecule. The coordination tended to be more efficient if a stronger Lewis acid was employed. The bipolar host material 35DCzPPy (14, Figure 5) was initially synthesized by Kido’s group [39]. It combines two carbazole electron donors with high triplet energy and a
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