The charge transport properties of dicyanomethylene-functionalised violanthrone derivatives

• Sondos A. J. Almahmoud,
• Joseph Cameron,
• Dylan Wilkinson,
• Michele Cariello,
• Claire Wilson,
• Alan A. Wiles,
• Peter J. Skabara and
• Graeme Cooke

Beilstein J. Org. Chem. 2024, 20, 2921–2930, doi:10.3762/bjoc.20.244

• dramatic increase in μh (1.07 × 10−2 cm2 V−1s−1) compared to the previously reported 2b (1.76 × 10−4 cm2 V−1s−1) [30]. On the other hand, the twisted configuration of the material’s backbone upon the introduction of dicyanomethylene groups, along with branched alkyl side chains in 3a, might have

Allostreptopyrroles A–E, β-alkylpyrrole derivatives from an actinomycete Allostreptomyces sp. RD068384

• Marwa Elsbaey,
• Naoya Oku,
• Mohamed S. A. Abdel-Mottaleb and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2024, 20, 1981–1987, doi:10.3762/bjoc.20.174

• 1997 to 2017, over fifty 5-alkylpyrrole-2-carbaldehydes and 5-alkyl-2-hydroxymethylpyrroles with diversely functionalized alkyl side chains have been isolated from sponges of the genus Mycale [7][11], but no additional 3-alkylpyrroles were reported so far. β-Alkylpyrroles are rare as microbial

Light on the sustainable preparation of aryl-cored dibromides

• Fabrizio Roncaglia,
• Alberto Ughetti,
• Nicola Porcelli,
• Biagio Anderlini,
• Andrea Severini and
• Luca Rigamonti

Beilstein J. Org. Chem. 2024, 20, 1076–1087, doi:10.3762/bjoc.20.95

• . Useful alkenyl functional groups can also be obtained by means of elimination processes, if proper alkyl side chains are present. Additional opportunities offered by C(sp3)–Hal bonds arise from the ease of their homolytic cleavage, leading to the formation of reactive carbon-centred radicals. C(sp2)–Hal

Quinoxaline derivatives as attractive electron-transporting materials

• Zeeshan Abid,
• Liaqat Ali,
• Sughra Gulzar,
• Faiza Wahad,
• Raja Shahid Ashraf and
• Christian B. Nielsen

Beilstein J. Org. Chem. 2023, 19, 1694–1712, doi:10.3762/bjoc.19.124

• chlorination effects on the Qx20 series, resulting in four new NFAs, i.e., Qx22–Qx25 (Figure 4). The research revealed the strategic balance between molecular crystallinity, packing, and optical properties. Qx24 and Qx25, with lower steric hindrance in the alkyl side chains, showed slightly decreased

Photoredox catalysis harvesting multiple photon or electrochemical energies

• Mattia Lepori,
• Simon Schmid and
• Joshua P. Barham

Beilstein J. Org. Chem. 2023, 19, 1055–1145, doi:10.3762/bjoc.19.81

Electro-conversion of cumene into acetophenone using boron-doped diamond electrodes

• Mana Kitano,
• Tsuyoshi Saitoh,
• Shigeru Nishiyama,
• Yasuaki Einaga and
• Takashi Yamamoto

Beilstein J. Org. Chem. 2022, 18, 1154–1158, doi:10.3762/bjoc.18.119

• -doped diamond electrode; electrosynthesis; oxidation; Introduction Selective oxidation of aromatic alkyl side chains is an important molecular transformation process to obtain various rubbers, resins, fine chemicals, and other industrial products [1][2]: terephthalic acid from p-xylene, cumene

New azodyrecins identified by a genome mining-directed reactivity-based screening

• Atina Rizkiya Choirunnisa,
• Kuga Arima,
• Yo Abe,
• Noritaka Kagaya,
• Kei Kudo,
• Hikaru Suenaga,
• Junko Hashimoto,
• Manabu Fujie,
• Noriyuki Satoh,
• Kazuo Shin-ya,
• Kenichi Matsuda and
• Toshiyuki Wakimoto

Beilstein J. Org. Chem. 2022, 18, 1017–1025, doi:10.3762/bjoc.18.102

• , together with 2D NMR spectra showed that compounds 8, 9, and 10 were azodyrecin derivatives with saturated alkyl side chains, which were named azodyrecin E (8), azodyrecin F (9), and azodyrecin G (10), respectively (Figure S3, Supporting Information File 1). Although azodyrecins characteristically possess

• branched alkyl side chains, compound 10 is the only azodyrecin analog with a straight alkyl chain. The configurations of the azoxy groups in 7–10 were determined to be Z, as in the case of other azodyrecins, according to the characteristic UV absorption at 221 nm (Figure S4 in Supporting Information File 1

• the unique methyl ester in azodyrecin The structural diversity of aliphatic azoxy natural products can be attributed to variations in the alkyl side chains and the amino acid-derived counterparts. The variation in the amino acid-derived units is considerably large, as it includes primary and secondary

Norbornadiene-functionalized triazatriangulenium and trioxatriangulenium platforms

• Roland Löw,
• Talina Rusch,
• Tobias Moje,
• Fynn Röhricht,
• Olaf M. Magnussen and
• Rainer Herges

Beilstein J. Org. Chem. 2019, 15, 1815–1821, doi:10.3762/bjoc.15.175

• deuterated benzene (right). Shown are the signals of the CH2 groups of the alkyl side chains next to the nitrogen atoms in the TATA platforms, which are indicative of the isomerization. Left bottom (blue): non-irradiated NBD 1a; left middle (red): pure QC 1b obtained after irradiation of 1b with 385 nm for

A conformationally adaptive macrocycle: conformational complexity and host–guest chemistry of zorb[4]arene

• Liu-Pan Yang,
• Song-Bo Lu,
• Arto Valkonen,
• Fangfang Pan,
• Kari Rissanen and
• Wei Jiang

Beilstein J. Org. Chem. 2018, 14, 1570–1577, doi:10.3762/bjoc.14.134

• ] and remote electronic substituents on the guests [34]. In addition, different alkyl side chains on oxatub[4]arenes lead to different macroscopic self-assembly behaviors [36]. Zorb[4]arene was first synthesized, reported and so named by the Georghiou group in 2005. The derivatives per-O-methoxy- and

Steric “attraction”: not by dispersion alone

• Ganna Gryn’ova and
• Clémence Corminboeuf

Beilstein J. Org. Chem. 2018, 14, 1482–1490, doi:10.3762/bjoc.14.125

• , i.e., ≈50% in interaction energy and 0.3 Å in interaction range. We discuss the implications of these results for the modeling of intermolecular interactions involving extended alkyl side chains, graphanes and various aliphatic systems in general. Results and Discussion Here, we investigate the nature

High performance p-type molecular electron donors for OPV applications via alkylthiophene catenation chromophore extension

• Paul B. Geraghty,
• Calvin Lee,
• Jegadesan Subbiah,
• Wallace W. H. Wong,
• James L. Banal,
• Mohammed A. Jameel,
• Trevor A. Smith and
• David J. Jones

Beilstein J. Org. Chem. 2016, 12, 2298–2314, doi:10.3762/bjoc.12.223

• performance OPV devices and the translation to large area and printed OPV devices. Chemical structures of molecular materials with the following variations; BTxR, alkyl side chains of the terthiophene bridging arm and BXR, oligothiophene bridging arm. BQR thermal and POM properties. a) DSC thermogram of BQR

Effect of the π-conjugation length on the properties and photovoltaic performance of A–π–D–π–A type oligothiophenes with a 4,8-bis(thienyl)benzo[1,2-b:4,5-b′]dithiophene core

• Ni Yin,
• Lilei Wang,
• Yi Lin,
• Jinduo Yi,
• Lingpeng Yan,
• Junyan Dou,
• Hai-Bo Yang,
• Xin Zhao and
• Chang-Qi Ma

Beilstein J. Org. Chem. 2016, 12, 1788–1797, doi:10.3762/bjoc.12.169

• fullerene derivative as the photoactive layer. This was ascribed to the influence of the orientation of the alkyl side chains. Although regioregular oligo(3-alkylthiophene)s are better building blocks for studying the effect of the π-conjugation length, only regioregular terthiophene (rr-3T) was reported to

• π-conjugation chain, or due to the steric hindrance effects of the alkyl side chains for the bigger molecules [29][30]. The absorption onset wavelength increases slightly with the increase of the π-bridge chain length, suggesting an extended π-conjugation system for the compounds with longer

Synthesis and characterization of benzodithiophene and benzotriazole-based polymers for photovoltaic applications

• Desta Gedefaw,
• Marta Tessarolo,
• Margherita Bolognesi,
• Mario Prosa,
• Renee Kroon,
• Wenliu Zhuang,
• Patrik Henriksson,
• Kim Bini,
• Ergang Wang,
• Michele Muccini,
• Mirko Seri and
• Mats R. Andersson

Beilstein J. Org. Chem. 2016, 12, 1629–1637, doi:10.3762/bjoc.12.160

• optical characterization, both in solution and thin-film, indicated that PTzBDT-1 has a red-shifted optical absorption compared to PTzBDT-2, likely due to a more planar conformation of the polymer backbone promoted by the lower content of alkyl side chains. The different aggregation in the solid state

• performance is presumably attributed to the limited solubility of the PTzBDT-1 in organic solvents resulting in enhanced aggregation and poor intermixing with the acceptor material in the active layer. Keywords: alkyl side chains; benzodithiophene; bulk heterojunction solar cells; 2D conjugated polymers

• polymers were determined using size exclusion chromatography and the results are summarized in Table 1. PTzBDT-2 showed a higher molecular weight (Mn = 41.7 kDa) due to the two n-hexyl solubilizing alkyl side chains per thiophene attached to the BDT core unit. On the contrary, PTzBDT-1 with a relatively

New synthetic strategies for xanthene-dye-appended cyclodextrins

• Milo Malanga,
• Andras Darcsi,
• Mihaly Balint,
• Gabor Benkovics,
• Tamas Sohajda and
• Szabolcs Beni

Beilstein J. Org. Chem. 2016, 12, 537–548, doi:10.3762/bjoc.12.53

• –5.5 ppm (Figure 4) is rather crowded and cannot be elucidated without the use of 2D techniques. On the other hand, the two signals in the aliphatic region can be easily assigned to the alkyl side chains of the rhodamine. Another important set of information that can be deduced/extrapolated from the

Self-assembled monolayers of shape-persistent macrocycles on graphite: interior design and conformational polymorphism

• Joscha Vollmeyer,
• Friederike Eberhagen,
• Sigurd Höger and
• Stefan-S. Jester

Beilstein J. Org. Chem. 2014, 10, 2774–2782, doi:10.3762/bjoc.10.294

• –alkynylene macrocycles are promising candidates as future mounts for functional units. These are separated from each other and cannot interact intermolecularly if the rings are adsorbed in parallel to the substrate. The exterior of the macrocycles can be substituted with alkyl side chains (or their alkoxy

• –HOPG and macrocycle–macrocycle interactions, the following key aspects must be considered: (i) how the extraannular alkyl side chains of the adsorbed macrocycles pack, and whether this can be compared to the packing of linear hydrocarbons on HOPG, (ii) how the specific attachment of the extraannular

• carbon backbones axially rotated by 90°; Figure 1b) and a deq of 0.35 nm [9][10][11][12]. Shape-persistent macrocycles on HOPG form non-covalent 2D assemblies held together by the van der Waals interaction between the alkyl side chains even without the presence of any additional functional groups [13][14

Removal of volatile organic compounds using amphiphilic cyclodextrin-coated polypropylene

• Ludmilla Lumholdt,
• Sophie Fourmentin,
• Thorbjørn T. Nielsen and
• Kim L. Larsen

Beilstein J. Org. Chem. 2014, 10, 2743–2750, doi:10.3762/bjoc.10.290

• of each of the VOCs by the different ACD derivatives is stated in µmol VOC/µmol CD cavity. The derivatives are ordered from lowest DS (10a) to highest DS (9). There does not seem to be any difference in the selectivity of the various ACD derivatives. If the alkyl side chains of the CD would have

• that the CD cavities and the alkyl side chains combine to form a very potent coating for the uptake of VOCs from an aqueous phase. As mentioned above, we previously hypothesised that the functionalisation method presented in this study results in the formation of multiple, alternating layers of CD

• , a small difference in the capacity when comparing 9 and 10c with 10a and 7, in other words, when comparing highly substituted ACDs with low-substituted ACDs. The fact that 9 and 10c have a higher uptake capacity but the same selectivity as the other derivatives could indicate that the alkyl side

Metal-free aerobic oxidations mediated by N-hydroxyphthalimide. A concise review

• Lucio Melone and
• Carlo Punta

Beilstein J. Org. Chem. 2013, 9, 1296–1310, doi:10.3762/bjoc.9.146

• hydroxamic acid and O2. NHPI-catalyzed reaction of adamantane under NO atmosphere. Nitration of alkanes and alkyl side-chains of aromatics. Radical mechanism for the nitration of alkanes catalyzed by NHPI. Benzyl alcohols from alkylbenzenes. Catalytic cycle of laccase-NHDs mediator oxidizing system. DADCAQ

Molecular length distribution and the formation of smectic phases

• Nadia Kapernaum,
• C. Scott Hartley,
• Jeffrey C. Roberts,
• Robert P. Lemieux and
• Frank Giesselmann

Beilstein J. Org. Chem. 2009, 5, No. 65, doi:10.3762/bjoc.5.65

• justification for this rather crude approximation, which neglects the flexibility of the alkyl side chains, is the general observation that the thickness of e.g. a smectic A layer (as observed in X-ray diffraction) is only slightly smaller than the fully extended length of the constituting mesogenic molecules