Organic electron transport materials

• Joseph Cameron and
• Peter J. Skabara

Beilstein J. Org. Chem. 2024, 20, 672–674, doi:10.3762/bjoc.20.60

• react with acceptors to produce reducing radical species, capable of reducing organic electron transport materials with a low electron affinity [4][5]. It is not only in modifying the molecular structure to improve the electron accepting ability that there is innovation in new organic electron transport

A laterally-fused N-heterocyclic carbene framework from polysubstituted aminoimidazo[5,1-b]oxazol-6-ium salts

• Andrew D. Gillie,
• Matthew G. Wakeling,
• Bethan L. Greene,
• Louise Male and
• Paul W. Davies

Beilstein J. Org. Chem. 2024, 20, 621–627, doi:10.3762/bjoc.20.54

• the C(oxazole)–N(sulfonamide) bond. No coalescence is observed at up to 110 °C indicating that these motifs might be useful as a robust atropisomeric system. The molecular structure of 13 and 14 have been unambiguously determined by single crystal X-ray diffraction (Scheme 2) [28]. The N–metal

Possible bi-stable structures of pyrenebutanoic acid-linked protein molecules adsorbed on graphene: theoretical study

• Yasuhiro Oishi,
• Motoharu Kitatani and
• Koichi Kusakabe

Beilstein J. Org. Chem. 2024, 20, 570–577, doi:10.3762/bjoc.20.49

• . Rotations around each bond can also happen and we expect similar steric hindrance effects to appear. Mechanical properties of PBA-linked molecular structure on graphene Here, we discuss possible conformations of the PBA-linked molecule. Would a similar activation barrier-type potential energy surface be

• conformation 1, 2, and the conformation at the saddle point, we measured the dihedral angles and the distance between two hydrogen atoms using Xcrysden [10]. (a) Molecular structure of 1-pyrenebutanoic acid succinimidyl ester (PASE). The black, white, red, and blue balls represent C, H, O, and N atoms

Synthesis of photo- and ionochromic N-acylated 2-(aminomethylene)benzo[b]thiophene-3(2Н)-ones with a terminal phenanthroline group

• Vladimir P. Rybalkin,
• Sofiya Yu. Zmeeva,
• Lidiya L. Popova,
• Irina V. Dubonosova,
• Olga Yu. Karlutova,
• Oleg P. Demidov,
• Alexander D. Dubonosov and
• Vladimir A. Bren

Beilstein J. Org. Chem. 2024, 20, 552–560, doi:10.3762/bjoc.20.47

• products 3a–c were comprehensively characterized by IR, 1Н and 13C NMR spectroscopy, HRMS (Supporting Information File 2) as well as by X-ray diffraction analysis. The molecular structure of 3b is shown in Figure 3. The crystal data, details of the data collection and refinements for 3b as well as complete

• of compound 2b in acetonitrile before (1) and after 15 s (2), 35 s (3), 75 s (4), 2.5 min (5) and 5 min (6) of irradiation with light of 436 nm (c 5.0 × 10−5 mol·L−1). Molecular structure of O-acylated isomer 3b. Thermal ellipsoids are drawn at the 50% probability level. Fragment of the molecular

Synthesis of 2,2-difluoro-1,3-diketone and 2,2-difluoro-1,3-ketoester derivatives using fluorine gas

• Alexander S. Hampton,
• David R. W. Hodgson,
• Graham McDougald,
• Linhua Wang and
• Graham Sandford

Beilstein J. Org. Chem. 2024, 20, 460–469, doi:10.3762/bjoc.20.41

• -generated N-fluoroammonium ion 7 to form 2-fluoro- and 2,2-difluoro-1,3-dicarbonyl products. Molecular structure of 2,2-difluoro-1,3-diphenylpropane-1,3-dione (3a). Crystal packing structure of 3f as determined by SXRC. Molecular structure and crystal packing of 5e as determined by SXRC. Monofluorination of

Facile approach to N,O,S-heteropentacycles via condensation of sterically crowded 3H-phenoxazin-3-one with ortho-substituted anilines

• Eugeny Ivakhnenko,
• Vasily Malay,
• Pavel Knyazev,
• Nikita Merezhko,
• Nadezhda Makarova,
• Oleg Demidov,
• Gennady Borodkin,
• Andrey Starikov and
• Vladimir Minkin

Beilstein J. Org. Chem. 2024, 20, 336–345, doi:10.3762/bjoc.20.34

• widened the scope and provided an access to derivatives of N,O- and N,S-heteropentacyclic quinoxalinophenoxazine, triphenodioxazine and oxazinophenothiazine systems. Keywords: 3H-phenoxazin-3-one; fluorescence; molecular structure; pentacyclic heterocycles; synthesis; Introduction 3H-Phenoxazin-3-one

• molecular structure of 5c was also determined using X-ray crystallography (Figure 4). We assumed that the scope of the reaction shown in Scheme 3 could be expanded via replacement of one of the amino groups of o-phenylenediamine by another strong nucleophilic center. It was earlier found [23] that

• -311++G(d,p) level) and distribution of electronic density in 6,8-di-tert-butyl-3H-phenoxazin-3-one (1): Mulliken charges and molecular electrostatic potential (MEP, isovalue = 0.004). Molecular structure of 6,8-di-tert-butyl-2-(o-nitrophenylamino)-3H-phenoxazin-3-one (4f). a) Selected bond distances

Photochromic derivatives of indigo: historical overview of development, challenges and applications

• Gökhan Kaplan,
• Zeynel Seferoğlu and
• Daria V. Berdnikova

Beilstein J. Org. Chem. 2024, 20, 228–242, doi:10.3762/bjoc.20.23

• ]. After the determination of the molecular structure of indigo in 1883, various precursors such as isatin (1), cinnamic acid (2), 2-nitrobenzaldehyde (3), aniline (4), 2-aminobenzoic acid (5), phenylglycine (6), 1-(1H-indol-1-yl)ethan-1-one (7) and indole (8) have been used in the synthesis (Figure 1) [4

• thermal half-lives of the photoisomers range from seconds to days. Detailed photophysical and photochemical studies have provided insight into the photoswitching mechanisms of indigo derivatives and enabled control of their photochemical properties through targeted design of the molecular structure. The

Comparison of glycosyl donors: a supramer approach

• Anna V. Orlova,
• Nelly N. Malysheva,
• Maria V. Panova,
• Nikita M. Podvalnyy,
• Michael G. Medvedev and
• Leonid O. Kononov

Beilstein J. Org. Chem. 2024, 20, 181–192, doi:10.3762/bjoc.20.18

• putative participation in stabilization [52][53] of the glycosyl cation. More importantly, in our opinion, this result indicates the existence of unexpected difficulties in the determination of relative reactivities of glycosyl donors (vide infra). Discussion It is generally believed that the molecular

• structure and the reaction mechanism are the keys to understanding chemical reactivity and selectivity [65][66][67]. In the area of carbohydrate chemistry, a lot of efforts are devoted to finding relationships between the fine details of molecular structures of both glycosylation partners (glycosyl donor

Using the phospha-Michael reaction for making phosphonium phenolate zwitterions

• Matthias R. Steiner,
• Max Schmallegger,
• Larissa Donner,
• Johann A. Hlina,
• Christoph Marschner,
• Judith Baumgartner and
• Christian Slugovc

Beilstein J. Org. Chem. 2024, 20, 41–51, doi:10.3762/bjoc.20.6

• in these cases (Supporting Information File 1, Figures S54 and S74). Crystal structures The solid-state structures of 2a and 2f were determined by single-crystal X-ray diffraction. The crystals were grown from concentrated solutions in toluene. A representation of the molecular structure of 2a is

• on the solid-state structure of 2a and the numbering scheme of the phenolate moiety. a) Molecular structure of 2a, hydrogen atoms omitted for clarity, thermal ellipsoids drawn at 30% probability level. Selected distances (Å) and angles (deg): P1–C6 = 1.758(2), P1–C15 = 1.824(2), P1–C18 = 1.814(2), P1

NMRium: Teaching nuclear magnetic resonance spectra interpretation in an online platform

• Luc Patiny,
• Hamed Musallam,
• Alejandro Bolaños,
• Michaël Zasso,
• Julien Wist,
• Metin Karayilan,
• Eva Ziegler,
• Johannes C. Liermann and
• Nils E. Schlörer

Beilstein J. Org. Chem. 2024, 20, 25–31, doi:10.3762/bjoc.20.4

• , and finally assign to a molecular structure. Students can then save the result of their work as .nmrium and submit it to the teacher who can then assess their solution and their solving strategy. Conclusion To the best of our knowledge, the software NMRium presented in this paper provides the first

Biphenylene-containing polycyclic conjugated compounds

• Cagatay Dengiz

Beilstein J. Org. Chem. 2023, 19, 1895–1911, doi:10.3762/bjoc.19.141

• with BBr3. In the final step, the integration of mesityl groups into the molecular structure, resulted in the production of both compounds 77 and 78, adopting v and z-configurations, respectively, in a 4 to 1 ratio. The synthesis of linear compound 84, characterized by a more extensive conjugated

Controlling the reactivity of La@C₈₂ by reduction: reaction of the La@C₈₂ anion with alkyl halide with high regioselectivity

• Yutaka Maeda,
• Saeka Akita,
• Mitsuaki Suzuki,
• Michio Yamada,
• Takeshi Akasaka,
• Kaoru Kobayashi and
• Shigeru Nagase

Beilstein J. Org. Chem. 2023, 19, 1858–1866, doi:10.3762/bjoc.19.138

• between the La@C2v-C82 adducts (2a–c, 3a–c, and 4a–c) [19] and the Ce@C2v-C82(CH2C6H3Me2) isomers [25] reported by Takano et al. was observed. Based on this observation, the plausible addition sites of 2a–c, 3a–c, and 4a–c were estimated to be at the C14, C10, and C18 positions. The molecular structure of

• ) an enlarged part view of blue region in (a). (c) Spin density of La@C2v-C82 as a function of its POAV values [34][35]. (d) Molecular structure of La@C2v-C82 and numbering carbon atoms. Reaction of the La@C2v-C82 anion with benzyl bromide derivatives. Charge densities and POAV values of carbon atoms

Selectivity control towards CO versus H₂ for photo-driven CO₂ reduction with a novel Co(II) catalyst

• Lisa-Lou Gracia,
• Philip Henkel,
• Olaf Fuhr and
• Claudia Bizzarri

Beilstein J. Org. Chem. 2023, 19, 1766–1775, doi:10.3762/bjoc.19.129

• ). Efforts to selectively achieve one polymorph, through differentiated crystallization processes, were unsuccessful. When analyzing the molecular structure in both crystals, the cobalt core is hexacoordinated, as expected. The two isothiocyanate ions are oriented cis to each other and trans to the

Charge carrier transport in perylene-based and pyrene-based columnar liquid crystals

• Alessandro L. Alves,
• Simone V. Bernardino,
• Carlos H. Stadtlober,
• Edivandro Girotto,
• Giliandro Farias,
• Rodney M. do Nascimento,
• Sergio F. Curcio,
• Thiago Cazati,
• Marta E. R. Dotto,
• Juliana Eccher,
• Leonardo N. Furini,
• Hugo Gallardo,
• Harald Bock and
• Ivan H. Bechtold

Beilstein J. Org. Chem. 2023, 19, 1755–1765, doi:10.3762/bjoc.19.128

• benzo[ghi]perylene-hexacarboxylic trialkylimide and 2 a dinaphtho[2,1-a;1,2-i]pyrene-tetracarboxylic dialkylimide, both with asymmetrically branched alkyl swallow-tails derived from 7-aminohexadecane (Scheme 1 illustrates their molecular structure). In Table 1, we show the thermal characteristics and

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

• (Voc), underscored the influence of the molecular structure [23]. A recent development by Liang et al. introduced Qx-derived double-cable conjugated polymers as a promising approach for improving the performance of single-component-OSCs (SCOSCs). They replaced the traditional benzothiadiazole core of Y

• moieties, the resulting PCE falls slightly short. This observation highlights the importance of a careful choice of auxiliary acceptors to ensure optimal device performance [42]. Godfroy and colleagues also emphasized the significance of molecular structure and backbone planarity in achieving efficient

• charge transport in DSSCs. Their work highlights the importance of molecular structure and backbone planarity in achieving efficient charge transport in DSSCs. The sensitizers, Qx36 and Qx37, employing Qx and dithieno[3,2-f:2',3'-h]quinoxaline acceptors, respectively, showed narrower absorption spectra

Tying a knot between crown ethers and porphyrins

• Maksym Matviyishyn and
• Bartosz Szyszko

Beilstein J. Org. Chem. 2023, 19, 1630–1650, doi:10.3762/bjoc.19.120

• nitrogen in the middle of the ether chain of 19-Cr. The reaction between in situ generated 17-K2 or 19-K2 and CoCl2 produced paramagnetic cobalt(II) complexes 17-Co or 19-Co [67]. The XRD analysis of 17-Co revealed a molecular structure with distorted octahedral Co(II) coordinating water and hydroxide

• ligands. Compound 19-Co (structure not shown) retained the cobalt(II) oxidation state with a water molecule within the cleft. The XRD analysis of the structures of 19-Co and 18b-Co exhibited Pacman conformation. The X-ray molecular structure of 19-Co provided further insights, showing a square-planar

• ) complex 40-Cu formation proving that 40 acts as a colourimetric sensor. The reaction of 38 with pyrrole in the presence of BF3:Et2O resulted in 41 incorporating a single pyrrole ring [132]. The attempted oxidation with DDQ afforded fused macrocycle 42 (Scheme 11). The X-ray molecular structure of 42

Cyclodextrins permeabilize DPPC liposome membranes: a focus on cholesterol content, cyclodextrin type, and concentration

• Ghenwa Nasr,
• Hélène Greige-Gerges,
• Sophie Fourmentin,
• Abdelhamid Elaissari and
• Nathalie Khreich

Beilstein J. Org. Chem. 2023, 19, 1570–1579, doi:10.3762/bjoc.19.115

• content membrane increase. Keywords: cholesterol; cyclodextrins; liposome; membrane permeability; Introduction Cyclodextrins (CDs) are a family of cyclic oligosaccharides made of glucopyranose units connected by α-1,4-glycosidic bonds. They possess a cone-shaped molecular structure with a hydrophobic

Synthesis of ether lipids: natural compounds and analogues

• Marco Antônio G. B. Gomes,
• Alicia Bauduin,
• Chloé Le Roux,
• Romain Fouinneteau,
• Wilfried Berthe,
• Mathieu Berchel,
• Hélène Couthon and
• Paul-Alain Jaffrès

Beilstein J. Org. Chem. 2023, 19, 1299–1369, doi:10.3762/bjoc.19.96

• ) where the molecular structure is altered. However, the incorporation of a saccharide unit or an inositol moiety is included in subsequent sections. Modulation sn-1: In 1986, Morris-Natschke et al. [129][130] reported a racemic synthesis of thioether analogues of edelfosine using thioglycerol as

Organic thermally activated delayed fluorescence material with strained benzoguanidine donor

• Alexander C. Brannan,
• Elvie F. P. Beaumont,
• Nguyen Le Phuoc,
• George F. S. Whitehead,
• Mikko Linnolahti and
• Alexander S. Romanov

Beilstein J. Org. Chem. 2023, 19, 1289–1298, doi:10.3762/bjoc.19.95

• containing a rigid benzoguanidine ligand in its molecular structure. Results and Discussion Synthesis and structure 4BGIPN was prepared in 70% yield by aromatic nucleophilic substitution reaction from 2,4,5,6-tetrafluoroisophthalonitrile and 5H-benzo[d]benzo[4,5]imidazo[1,2-a]imidazole (benzoguanidine) after

The effect of dark states on the intersystem crossing and thermally activated delayed fluorescence of naphthalimide-phenothiazine dyads

• Liyuan Cao,
• Xi Liu,
• Xue Zhang,
• Jianzhang Zhao,
• Fabiao Yu and
• Yan Wan

Beilstein J. Org. Chem. 2023, 19, 1028–1046, doi:10.3762/bjoc.19.79

• intersystem crossing (rISC) is slow, without coupling with an approximate 3LE state. These studies are useful for an in-depth understanding of the photophysical mechanisms of the TADF emitters, as well as for molecular structure design of new electron donor–acceptor TADF emitters. Keywords: charge-transfer

• harvesting efficiency of both the singlet and triplet excitons and thus a high quantum efficiency for the electroluminescence [13]. The TADF emission process involves the reverse intersystem crossing (rISC) from the triplet (T1) state to the emissive singlet (S1) state. A typical molecular structure motif

• not changed by the unique molecular structure modification method [51]. This approach is useful for studying molecules showing complicated, entangled photophysical processes upon photoexcitation, for instance the electron donor–acceptor type of TADF emitters [44][46]. Recently, we reported NI-PTZ

Cyclodextrins as building blocks for new materials

• Miriana Kfoury and
• Sophie Fourmentin

Beilstein J. Org. Chem. 2023, 19, 889–891, doi:10.3762/bjoc.19.66

• . CDs are the most studied supramolecular hosts. They provide the most extensive database on molecular recognition in the literature, with more than 100,000 publications [2]. CDs owe their success not only to the unique molecular structure [3], which allows them to act as host compounds, but also to

Bromination of endo-7-norbornene derivatives revisited: failure of a computational NMR method in elucidating the configuration of an organic structure

• Demet Demirci Gültekin,
• Arif Daştan,
• Yavuz Taşkesenligil,
• Cavit Kazaz,
• Yunus Zorlu and
• Metin Balci

Beilstein J. Org. Chem. 2023, 19, 764–770, doi:10.3762/bjoc.19.56

• ppm). NOE-Diff experiment. Irradiation at the resonance frequency of proton H7 (4.23 ppm). A) Molecular structure of the compound 6 with displacement ellipsoids drawn at the 30% probability level. H-atoms are shown as small spheres of arbitrary radii. B) Perspective view of the crystal packing of

Synthesis, structure, and properties of switchable cross-conjugated 1,4-diaryl-1,3-butadiynes based on 1,8-bis(dimethylamino)naphthalene

• Semyon V. Tsybulin,
• Ekaterina A. Filatova,
• Alexander F. Pozharskii,
• Valery A. Ozeryanskii and
• Anna V. Gulevskaya

Beilstein J. Org. Chem. 2023, 19, 674–686, doi:10.3762/bjoc.19.49

• ). Molecular structure of compound 11c: frontal (top; BF4− omitted) and side views (bottom; hydrogen atoms omitted). Calculation of the qr parameter. Two π-conjugation ways in oligomers 5. UV–vis spectra of oligomers 5 (blue line), monomers 6 (red line), and butadiyne 1 (green line). UV–vis spectra of salts 11

Combining the best of both worlds: radical-based divergent total synthesis

• Kyriaki Gennaiou,
• Antonios Kelesidis,
• Maria Kourgiantaki and
• Alexandros L. Zografos

Beilstein J. Org. Chem. 2023, 19, 1–26, doi:10.3762/bjoc.19.1

• libraries. But how big should this chemical space be, so as to actually address our needs? A general consensus has emerged, supporting that “it is not actually the library size but rather the library diversity in terms of molecular structure and function which is fundamental for a successful drug discovery

Redox-active molecules as organocatalysts for selective oxidative transformations – an unperceived organocatalysis field

• Elena R. Lopat’eva,
• Igor B. Krylov,
• Dmitry A. Lapshin and
• Alexander O. Terent’ev

Beilstein J. Org. Chem. 2022, 18, 1672–1695, doi:10.3762/bjoc.18.179

• recent years are covered here. The present article is aimed at the summarization of main molecular structure types employed in redox organocatalysis, the consolidation of this research field, and highlighting possible areas of further development. Discussion The present article is aimed at the