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Search for "aromatic hydrocarbon" in Full Text gives 21 result(s) in Beilstein Journal of Organic Chemistry.
Synthesis and characterizations of highly luminescent 5-isopropoxybenzo[rst]pentaphene
Beilstein J. Org. Chem. 2025, 21, 270–276, doi:10.3762/bjoc.21.19
- by scanning electron microscopy. The intriguing optical properties of BPP and its derivatives may lead to their application as fluorophores. Keywords: benzo[rst]pentaphene; intramolecular charge transfer; nanocrystals; photoluminescence; polycyclic aromatic hydrocarbon; Introduction Polycyclic
Surprising acidity for the methylene of 1,3-indenocorannulenes?
Beilstein J. Org. Chem. 2024, 20, 3144–3150, doi:10.3762/bjoc.20.260
- -perfluorophenylfluorene (28.14 in CH3CN). This work reports quantitative pKa values of BFC and FIC, places those values in a broadened context of CpH-cognate hydrocarbon acidity and presents a Clar–Loschmidt graph perspective to help understand the “surprises”. Keywords: acidity; aromatic hydrocarbon; Clar sextet
- values (i.e., show similar acidity). The extreme of this graph example is the five rim benzene elements and a Cp− core, pentabenzocorannulene (Scheme 3, upper) [19][20]. Such a CpH derivative should be a very acidic aromatic hydrocarbon, and computations for this study predict its pKa to be ca 1.1 in
- aromatic hydrocarbon acidities I. Results of pKa measurements in acetonitrile. Acknowledgements High-performance computational work was carried out using the supercomputer at SPST Tianjin University. Funding Experimental work at Tartu was carried out using the instrumentation at the Estonian Center of
Synthesis and reactivity of the di(9-anthryl)methyl radical
Beilstein J. Org. Chem. 2024, 20, 2254–2260, doi:10.3762/bjoc.20.193
- aromatic hydrocarbon radicals, which can persist in air-saturated solutions for several days to months, have been synthesized by employing bulky substituents around the spin-localized carbon center [13][14][15]. These stable radicals have paved the way to elucidate the nature of radical species, advancing
- the field of radical chemistry. However, reducing the reactivity of radical species can mean losing one of their most attractive properties. Therefore, it is very important to explore aromatic hydrocarbon radicals that are sufficiently stable for handling, yet reactive under specific conditions
- . Previously, we reported aromatic hydrocarbon radicals with 9-anthryl (Ant) units at the spin-center carbon, exhibiting high stability (Figure 1a) [16][17][18][19][20][21]. Although bulky phenyl substitutions at the spin-center carbon can also provide high stability [13][14][15], the introduction of an Ant
Synthesis of polycyclic aromatic quinones by continuous flow electrochemical oxidation: anodic methoxylation of polycyclic aromatic phenols (PAPs)
Beilstein J. Org. Chem. 2024, 20, 1746–1757, doi:10.3762/bjoc.20.153
- . The specific quinones formed were guided by the position of an initial hydroxy group on the polycyclic aromatic hydrocarbon. An available para-position in the PAPs gave p-quinones, while hydroxy groups in the 2- or 3-position led to o-quinones. The substrates were analysed by cyclic voltammetry for
Bismuth(III) triflate: an economical and environmentally friendly catalyst for the Nazarov reaction
Beilstein J. Org. Chem. 2024, 20, 1167–1178, doi:10.3762/bjoc.20.99
- synthesis has been reported for several transformations, such as epoxide opening [56], ketal formation and deprotection [57][58], Mannich reaction [59], intramolecular Sakurai cyclization [60], alcohol oxidation [61], aromatic hydrocarbon nitration [62], imine allylation [63], Knoevenagel condensation [64
Spin and charge interactions between nanographene host and ferrocene
Beilstein J. Org. Chem. 2024, 20, 1011–1019, doi:10.3762/bjoc.20.89
- depletion, is attracting much attention due to its potential for creating a new class of functional materials with various guest molecules [1]. In particular, nanosized graphene called nanographene, the macroscopic limit of polycyclic aromatic hydrocarbon molecules, is a magnetic host material with spins
Switchable molecular tweezers: design and applications
Beilstein J. Org. Chem. 2024, 20, 504–539, doi:10.3762/bjoc.20.45
Electrochemical and spectroscopic properties of twisted dibenzo[g,p]chrysene derivatives
Beilstein J. Org. Chem. 2022, 18, 963–971, doi:10.3762/bjoc.18.96
- , a strong photoluminescence was observed for DBC-H and DBC-Si. Keywords: DFT calculation; dibenzo[g,p]chrysenes; fluorescent compounds; oxidation; polycyclic aromatic hydrocarbon (PAH); twisted acenes; Introduction Polycyclic aromatic hydrocarbons (PAHs) have attracted interest as potential
Chemical syntheses and salient features of azulene-containing homo- and copolymers
Beilstein J. Org. Chem. 2021, 17, 2164–2185, doi:10.3762/bjoc.17.139
- Vijayendra S. Shetti Department of Chemistry, National Institute of Technology Karnataka, Surathkal 575025, India 10.3762/bjoc.17.139 Abstract Azulene is a non-alternant, aromatic hydrocarbon with many exciting characteristics such as having a dipole moment, bright color, stimuli responsiveness
- -containing homo- and copolymers, including brief descriptions of their key properties. Keywords: azulene; chemical synthesis; copolymer; non-alternant hydrocarbon; organic electronics; polyazulene; Introduction Azulene (C10H8) is a non-alternant, non-benzenoid, 10 π electron aromatic hydrocarbon containing
Recent advances in the syntheses of anthracene derivatives
Beilstein J. Org. Chem. 2021, 17, 2028–2050, doi:10.3762/bjoc.17.131
- years (2008–2020) and focuses on direct and indirect methods to construct anthracene and anthraquinone frameworks. Keywords: anthracenes; anthraquinones; Friedel–Crafts cyclization; intramolecular cyclization; metal-catalyzed; Introduction Anthracene is an important aromatic hydrocarbon consisting of
Synthetic approaches to bowl-shaped π-conjugated sumanene and its congeners
Beilstein J. Org. Chem. 2020, 16, 2212–2259, doi:10.3762/bjoc.16.186
- ’ “Suman”, which means “Sunflower”), a beautifully simple yet much effective bowl-shaped C3-symmetric polycyclic aromatic hydrocarbon having three benzylic positions clipped between three phenyl rings in the triphenylene framework has attracted a tremendous attention of researchers worldwide. Therefore
Six-fold C–H borylation of hexa-peri-hexabenzocoronene
Beilstein J. Org. Chem. 2020, 16, 391–397, doi:10.3762/bjoc.16.37
- , Nagoya, 464-8602, Japan 10.3762/bjoc.16.37 Abstract Hexa-peri-hexabenzocoronene (HBC) is known to be a poorly soluble polycyclic aromatic hydrocarbon for which direct functionalization methods have been very limited. Herein, the synthesis of hexaborylated HBC from unsubstituted HBC is described. Iridium
A novel and efficient synthesis of phenanthrene derivatives via palladium/norbornadiene-catalyzed domino one-pot reaction
Beilstein J. Org. Chem. 2019, 15, 291–298, doi:10.3762/bjoc.15.26
- substrate range, shorter reaction times and higher yields of products than previously reported methods. Keywords: C–H activation; norbornadiene; palladium; phenanthrene derivatives; Introduction Phenanthrene is a polycyclic aromatic hydrocarbon which contains three benzene rings. The phenanthrenes can be
An overview of recent advances in duplex DNA recognition by small molecules
Beilstein J. Org. Chem. 2018, 14, 1051–1086, doi:10.3762/bjoc.14.93
- small molecules comprise various heterocyclic and/or aromatic hydrocarbon rings with limited rotational freedom and torsion, allowing these drugs to fit into major/minor grooves of DNA by displacing water molecules from the spine of hydration as shown in the Figure 2 [25][26][27]. These molecules bind
Pyrene–nucleobase conjugates: synthesis, oligonucleotide binding and confocal bioimaging studies
Beilstein J. Org. Chem. 2017, 13, 2521–2534, doi:10.3762/bjoc.13.249
- . Confocal microscopy confirmed that 5 predominantly stains mitochondria but it also accumulates in the nucleoli of the cells. Keywords: confocal microscopy; luminescence; nucleobases; oligonucleotide binding; pyrene; X-ray; Introduction Pyrene is a planar, polycyclic aromatic hydrocarbon which shows well
Facile synthesis of 4H-chromene derivatives via base-mediated annulation of ortho-hydroxychalcones and 2-bromoallyl sulfones
Beilstein J. Org. Chem. 2016, 12, 16–21, doi:10.3762/bjoc.12.3
- . Polycyclic aromatic hydrocarbon frameworks (naphthalene and anthracene rings) as well as a representative heterocyclic ring (furan) may be incorporated into the 4H-chromene skeleton product by using chalcones (7c, 7d, and 7e, respectively) functionalized with these moieties. Disappointingly, attempts to
Aryl substitution of pentacenes
Beilstein J. Org. Chem. 2014, 10, 1692–1705, doi:10.3762/bjoc.10.178
- ; pentacene; π-stacking; polycyclic aromatic hydrocarbon; solid-state structure; Introduction Conjugated organic molecules are promising candidates for use in optoelectronic applications including OLEDs [1], photovoltaics [2], and OFETs [3]. Even though there is literally an infinite number of possibilities
Influence of perylenediimide–pyrene supramolecular interactions on the stability of DNA-based hybrids: Importance of electrostatic complementarity
Beilstein J. Org. Chem. 2014, 10, 1589–1595, doi:10.3762/bjoc.10.164
- sciences. They play a crucial role in the stacking of nucleobases, thus stabilising the DNA double helix. The following paper describes a series of chimeric DNA–polycyclic aromatic hydrocarbon (PAH) hybrids. The PAH building blocks are electron-rich pyrene and electron-poor perylenediimide (PDI), and were
- molecular scaffold for arranging various types of chromophores [39][40][41][42][43][44]. Recently, we reported that oligoarenotides (oligomers with an alternating phosphodiester-aromatic hydrocarbon motif) exhibit similar structural properties as nucleic acids, and although the aromatic hydrocarbons cannot
Site-selective covalent functionalization at interior carbon atoms and on the rim of circumtrindene, a C36H12 open geodesic polyarene
Beilstein J. Org. Chem. 2014, 10, 956–968, doi:10.3762/bjoc.10.94
- ; polycyclic aromatic hydrocarbon; Prato reaction; Introduction Investigations into the structures and properties of geodesic polyarenes began with the synthesis of corannulene (1, C20H10) in 1966 [1][2] and were greatly stimulated by the discovery of buckminsterfullerene (2, C60) in 1985 (Figure 1) [3
- formation at an interior carbon atom, despite the long history of aromatic hydrocarbon chemistry [41][42]. These PAHs (1 and 10) are obviously nonplanar and have the same patterns of pentagons and hexagons as that found on the surface of fullerene C60. The distortions of the π-systems in these molecules
Gold-catalyzed intermolecular coupling of sulfonylacetylene with allyl ethers: [3,3]- and [1,3]-rearrangements
Beilstein J. Org. Chem. 2013, 9, 1724–1729, doi:10.3762/bjoc.9.198
- = di-t-butyl-o-biphenylphosphine, JohnPhos) formed in situ was used as catalyst, the reaction was more efficient in chlorinated solvents rather than polar aprotic or aromatic hydrocarbon solvents (Table 1, entries 1–7). Contrary to the previous [4 + 2] cycloaddition, formal enyne cross metathesis or [2
About the activity and selectivity of less well-known metathesis catalysts during ADMET polymerizations
Beilstein J. Org. Chem. 2010, 6, 1149–1158, doi:10.3762/bjoc.6.131
- C1 to challenging substrates, such as diethyl di(methallyl)malonate in fluorinated aromatic hydrocarbon solvents, resulted in a remarkable enhancement of catalytic activity. Moreover, this approach was successfully extended to the RCM of natural products and the cross-metathesis formation of
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