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Search for "π–π interaction" in Full Text gives 45 result(s) in Beilstein Journal of Organic Chemistry.
Deep-blue emitting 9,10-bis(perfluorobenzyl)anthracene
Beilstein J. Org. Chem. 2025, 21, 515–525, doi:10.3762/bjoc.21.39
- photochemical reaction. Its structure was elucidated by NMR spectroscopy and single crystal X-ray diffractometry. The latter revealed no π–π interaction between neighboring ANTH cores. A combination of high photoluminescence quantum yield (PLQY) of 0.85 for 9,10-ANTH(BnF)2, its significantly improved
The effect of neighbouring group participation and possible long range remote group participation in O-glycosylation
Beilstein J. Org. Chem. 2025, 21, 369–406, doi:10.3762/bjoc.21.27
- 9-anthracenylmethyl group in the C-2 position which rendered neighbouring group participation effectively via a favourable π–π interaction between the p-orbitals of the stabilised oxonium ion intermediate and the aromatic ring of the protecting group to yield 1,2-trans selective products. Increasing
Recent advances in organocatalytic atroposelective reactions
Beilstein J. Org. Chem. 2025, 21, 55–121, doi:10.3762/bjoc.21.6
- , previous findings from the literature, and experimental results, a reaction mechanism was proposed [46]. Hydrogen bonding as well as π–π interaction with the catalyst (R)-C22 activates both substrates in the stable intermediate Int-35. This stabilized state ensures the concerted control of
The charge transport properties of dicyanomethylene-functionalised violanthrone derivatives
Beilstein J. Org. Chem. 2024, 20, 2921–2930, doi:10.3762/bjoc.20.244
- contributed to a lower intermolecular π–π interaction and, therefore, lower μh (3.62 × 10−6 cm2 V−1 s−1) compared to the previously reported 2a (4.93 × 10−5 cm2 V−1 s−1) [30]. Conclusion Violanthrone derivatives represent a promising group of semiconductor materials for organic electronics. It has been shown
Interaction of a pyrene derivative with cationic [60]fullerene in phospholipid membranes and its effects on photodynamic actions
Beilstein J. Org. Chem. 2024, 20, 2732–2738, doi:10.3762/bjoc.20.231
- safer control of Vm. Keywords: liposome; π–π interaction; reactive oxygen species; superoxide radical anion; Introduction The [60]fullerene (C60) is known as an excellent electron acceptor [1][2] and is commonly used in organic solar cell applications [3]. Taking advantage of the fact that C60 can be
Competing electrophilic substitution and oxidative polymerization of arylamines with selenium dioxide
Beilstein J. Org. Chem. 2024, 20, 1221–1235, doi:10.3762/bjoc.20.105
- structure, it self-organized through π–π interaction between the oxamide motif and the aryl π-framework. Further, the CH…O=C interaction facilitated the formation of ladder-like packing in the solid state (Figure S36, Supporting Information File 1). The molecular structure of oxamide 13 is shown in Figure 3
Charge carrier transport in perylene-based and pyrene-based columnar liquid crystals
Beilstein J. Org. Chem. 2023, 19, 1755–1765, doi:10.3762/bjoc.19.128
- derivatives are among the most investigated due to their easy functionalization, high chemical and thermal stability, strong photoluminescence, and n-type semiconductor character. They tend to adopt columnar organization due to the strong π–π interaction of the rigid cores, providing a path for the efficient
Quinoxaline derivatives as attractive electron-transporting materials
Beilstein J. Org. Chem. 2023, 19, 1694–1712, doi:10.3762/bjoc.19.124
- , resulting in an efficiency of 18% and marking a significant advancement in OSC research [27]. Zhou and co-workers synthesized Y6-type NFA acceptors, Qx12 and Qx13, by substituting Y6’s benzothiadiazole ring with a Qx moiety. Qx13 exhibited a stronger π–π interaction compared to Qx12, which facilitated
Aromatic C–H bond functionalization through organocatalyzed asymmetric intermolecular aza-Friedel–Crafts reaction: a recent update
Beilstein J. Org. Chem. 2023, 19, 956–981, doi:10.3762/bjoc.19.72
- bond formed between the imine nitrogen of 49 and the catalyst’s OH group (see transition state 84). These dual H-bonding interactions were assisted by a π–π interaction between the arene rings of both the electrophile and nucleophile that helped in the formation of a stereodefined transition state. The
Asymmetric organocatalytic Michael addition of cyclopentane-1,2-dione to alkylidene oxindole
Beilstein J. Org. Chem. 2022, 18, 167–173, doi:10.3762/bjoc.18.18
- ). When instead of a benzylidene-containing substrate an alkylidene with an extra ester moiety was used, the enantioselectivity was lost and the product 3i was obtained as a racemic mixture. Either additional coordination with the catalyst or a lack of π–π-interaction may have been responsible for that
Recent advances in the asymmetric phosphoric acid-catalyzed synthesis of axially chiral compounds
Beilstein J. Org. Chem. 2021, 17, 2729–2764, doi:10.3762/bjoc.17.185
- -naphthylamine and azodicarboxylate through a dual hydrogen bond activation mode and a π–π interaction strategy (Scheme 31) [2]. Diarylamines and related scaffolds are among the most common potentially atropisomeric chemotypes in medicinal chemistry. For example, the drugs binimetinib and bosutinib contain
In-depth characterization of self-healing polymers based on π–π interactions
Beilstein J. Org. Chem. 2021, 17, 2496–2504, doi:10.3762/bjoc.17.166
- second phase transition of the PEG moieties observed in the DSC. Nevertheless, at 150 °C, P2 also shows the clear broadening of bands, which is consistent with the very similar positions for the perylene π–π interaction signal in the DSC. All these findings clearly support that at increased temperatures
- , which correlates to the changes of the molecular structure. Furthermore, the scratch healing was analyzed in detail showing that only one of the two polymers studied, polymer P1 is able to heal scratches in a sufficient manner at temperature higher than the activation of the π–π interaction. In contrast
Multiswitchable photoacid–hydroxyflavylium–polyelectrolyte nano-assemblies
Beilstein J. Org. Chem. 2021, 17, 166–185, doi:10.3762/bjoc.17.17
- molecular recognition processes have been established based on different non-covalent interactions such as hydrogen bonding [9][10][11][12], π–π interaction [13][14][15][16][17], hydrophobic effects, and amphiphilicity [18][19][20][21]. It has been highly desirable to establish concepts that could be
Synthesis, crystal structures and properties of carbazole-based [6]helicenes fused with an azine ring
Beilstein J. Org. Chem. 2021, 17, 11–21, doi:10.3762/bjoc.17.2
- in its length from the standard single C(sp2)–C(sp2) bond (ca. 1.48 Å). The X-ray analysis of quinoxaline-fused [6]helicene 10a revealed the presence of the face-to-face π–π interaction between the helicene aggregates. The racemic aggregation was composed by (P)- and (M)-enantiomers on the manner of
Thermodynamic and electrochemical study of tailor-made crown ethers for redox-switchable (pseudo)rotaxanes
Beilstein J. Org. Chem. 2020, 16, 2576–2588, doi:10.3762/bjoc.16.209
- non-folded conformation. The torsional angle between the central phenyl ring and the NDI is 84.2° in order to avoid strain between the protons of the resorcinol and the carbonyl groups of the NDI. Consequently, an intramolecular π–π-interaction with the naphthalene on the other side of the macrocycle
Highly selective Diels–Alder and Heck arylation reactions in a divergent synthesis of isoindolo- and pyrrolo-fused polycyclic indoles from 2-formylpyrrole
Beilstein J. Org. Chem. 2020, 16, 1320–1334, doi:10.3762/bjoc.16.113
- ) [58][59][65]. Regarding the addition of diene 8c with the N-methylmaleimide (7b), a π···π interaction is discarded. Nevertheless, the endo adduct 9g was obtained as the major diastereoisomer (Table 2, entry 7). The calculated geometry at the endo TS reveals a plausible Cmethyl–H···π interaction, based
Synthesis, antiinflammatory activity, and molecular docking studies of bisphosphonic esters as potential MMP-8 and MMP-9 inhibitors
Beilstein J. Org. Chem. 2020, 16, 1277–1287, doi:10.3762/bjoc.16.108
- was occupying the entire pocket was compound 6 due to the formation of four hydrogen bonds and a favourable π–π interaction between the methoxybenzyl group and His197. Only for 3 and 4, one of the oxygen atoms of the phosphonate units was the most contributing atom to the interaction energy. However
Recent applications of porphyrins as photocatalysts in organic synthesis: batch and continuous flow approaches
Beilstein J. Org. Chem. 2020, 16, 917–955, doi:10.3762/bjoc.16.83
- (1.87 nm), acts as a size-selective photocatalyst. Furthermore, the photocatalytic activity of 2D-COF is lower due to the π–π interaction between framework layers. Nitrogen oxidation: Amines are well-known as very efficient physical and chemical quenchers for singlet oxygen [67][100][101]. A myriad of
Design and synthesis of diazine-based panobinostat analogues for HDAC8 inhibition
Beilstein J. Org. Chem. 2020, 16, 628–637, doi:10.3762/bjoc.16.59
- indole ring of TOI4 was also contorted upward, forming a T-shaped π–π interaction with Phe-207 while both the indole rings of TOI1 and TOI2 were shown to be flipped downward forming a T-shaped π–π interaction with Phe-208. TOI4 is the only diazine compound having two nitrogens directly next to each other
- -rev is tilted downward forming a T-shaped π–π interaction with Phe-208. In review of the computational results, the inclusion of the nitrogen atoms in the core ring structure of panobinostat produced compounds with predicted binding affinities similar to panobinostat. Thus, aiming to develop improved
Efficient synthesis of 3,6,13,16-tetrasubstituted-tetrabenzo[a,d,j,m]coronenes by selective C–H/C–O arylations of anthraquinone derivatives
Beilstein J. Org. Chem. 2020, 16, 544–550, doi:10.3762/bjoc.16.51
- ,j,m]coronene 7aa was also examined (Figure 2), as Wu and co-workers have studied the self-assembling property of the tetrabenzo[a,d,j,m]coronene derivative possessing n-octyl groups at the 2, 7, 12, and 17-positions by 1H NMR spectroscopy and suggested its intermolecular π–π interaction in solution
- 5 × 10−4 M at rt also led to a downfield shift and sharpening of the signals. These observations suggest that 7aa assembles by intermolecular π–π interaction in CDCl3 as was seen by Wu and co-workers for their compound possessing substituents at different positions. Conclusion The synthesis of a new
Six-fold C–H borylation of hexa-peri-hexabenzocoronene
Beilstein J. Org. Chem. 2020, 16, 391–397, doi:10.3762/bjoc.16.37
- bonds of HBC (Figure 3a). An equivalent amount of pentane for 1 was co-crystallized. As illustrated in Figure 3b and 3c, 1 is slightly distorted to have S6 symmetry, and no π–π interaction is observed in the packing mode reflecting the steric hindrance of boryl groups. This result corresponds with the
Synthesis and herbicidal activities of aryloxyacetic acid derivatives as HPPD inhibitors
Beilstein J. Org. Chem. 2020, 16, 233–247, doi:10.3762/bjoc.16.25
- inhibitors. Initially, molecular docking studies were performed on two representative compounds, namely I39 and I40 [25], in order to explore their binding modes. The result revealed the presence of two main interactions, the sandwich π−π interaction and the bidentate interaction, which are similar to those
Mechanochemical synthesis of hyper-crosslinked polymers: influences on their pore structure and adsorption behaviour for organic vapors
Beilstein J. Org. Chem. 2019, 15, 1154–1161, doi:10.3762/bjoc.15.112
- reached at ca. 40% lower loading compared to benzene. This data points out the significantly favoured adsorption of benzene due to aromatic π–π interaction in comparison to the significantly weaker bonding of aliphatic cyclohexane. Conclusion Summing up, we have demonstrated that mechanochemistry can be a
- experiments the adsorption of benzene was favoured over cyclohexane by strong π–π interaction with the aromatic framework. This has been proven by differences in uptake as well as by comparison of isosteric heat of adsorptions as direct indicator of the adsorption interactions. Experimental In our standard
Targeting the Pseudomonas quinolone signal quorum sensing system for the discovery of novel anti-infective pathoblockers
Beilstein J. Org. Chem. 2018, 14, 2627–2645, doi:10.3762/bjoc.14.241
- (His71) sidechain via π-stacking. For the thiophene-containing fragment 26 a π–π interaction of the sulfur with Phe195 can be observed. In vitro evaluation was performed using a combined PqsDE assay due to the aforementioned instability of 2-ABA-CoA which in this scenario is generated in situ from
Evaluation of dispersion type metal···π arene interaction in arylbismuth compounds – an experimental and theoretical study
Beilstein J. Org. Chem. 2018, 14, 2125–2145, doi:10.3762/bjoc.14.187
- contribute to the overall dispersion from π···π interactions. In case of polymorph 1c the results of the quantification of the interaction energies reveal that this structure is actually not dominated by Bi···π arene interaction, but rather consists of dimers connected by strong π···π interaction (Figure 16
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