Enhanced host–guest interaction between [10]cycloparaphenylene ([10]CPP) and [5]CPP by cationic charges

• Eiichi Kayahara,
• Yoshiyuki Mizuhata and
• Shigeru Yamago

Beilstein J. Org. Chem. 2024, 20, 436–444, doi:10.3762/bjoc.20.38

• ). Furthermore, the tilting of the complex in adjacent columnar structures with respect to the short axis is opposite to each other, as in a herringbone structure, and such columnar structures are parallel to each other through a columnar structure consisting of a host–guest complex in blue and its counterions

Multi-redox indenofluorene chromophores incorporating dithiafulvene donor and ene/enediyne acceptor units

• Christina Schøttler,
• Kasper Lund-Rasmussen,
• Line Broløs,
• Philip Vinterberg,
• Ema Bazikova,
• Viktor B. R. Pedersen and
• Mogens Brøndsted Nielsen

Beilstein J. Org. Chem. 2024, 20, 59–73, doi:10.3762/bjoc.20.8

• Crystals suitable for single-crystal X-ray diffraction studies were obtained for compounds 25, 26, and 29. Their structures are shown in Figure 10, top, and their respective crystal packings below. All three compounds pack in a herringbone manner in the crystal structure, with the major difference that

• compound 29 is perpendicular with respect to the herringbone pattern and the related structures (see Figure 10, bottom). Compound 25 packs with an intramolecular distance of 3.41 Å between the planes of the π-systems. Neither compound 26 nor 29 shows π–π interactions in the crystal packing. The large

Comparison of crystal structure and DFT calculations of triferrocenyl trithiophosphite’s conformance

• Ruslan P. Shekurov,
• Mikhail N. Khrizanforov,
• Ilya A. Bezkishko,
• Tatiana P. Gerasimova,
• Almaz A. Zagidullin,
• Daut R. Islamov and
• Vasili A. Miluykov

Beilstein J. Org. Chem. 2022, 18, 1499–1504, doi:10.3762/bjoc.18.157

• )3PS [7] (Figure 4). All three compounds form crystals belonging to the monoclinic syngony. In all three cases, the molecules in the crystals form a herringbone motif. In (FcS)3P, C–H···π interactions dominate, while in (FcS)3PS and (FcS)3PO, in addition to C–H···π interactions, by one C–H···S and two

A comprehensive review of flow chemistry techniques tailored to the flavours and fragrances industries

• Guido Gambacorta,
• James S. Sharley and
• Ian R. Baxendale

Beilstein J. Org. Chem. 2021, 17, 1181–1312, doi:10.3762/bjoc.17.90

Synthetic approaches to bowl-shaped π-conjugated sumanene and its congeners

• Shakeel Alvi and
• Rashid Ali

Beilstein J. Org. Chem. 2020, 16, 2212–2259, doi:10.3762/bjoc.16.186

• the pyrene moiety, an appealing sumanene derivative 93, namely as pyrenylsumanene, was constructed by the groups of Higashibayashi and Sakurai which display both herringbone and columnar crystal packing (Scheme 22) [53]. To synthesize this architecturally interesting molecule, they began with the

Synthesis of 6,13-difluoropentacene

• Matthias W. Tripp and
• Ulrich Koert

Beilstein J. Org. Chem. 2020, 16, 2136–2140, doi:10.3762/bjoc.16.181

• herringbone structure of 1–3. Here, the synthesis and characterization of 6,13-difluoropentacene (5, F2PEN) is reported. Since the central ring of pentacenes is known to be a weak spot (because of light-induced dimerization or oxidation) [2] the effects of fluorination in these positions are of interest

Selenophene-containing heterotriacenes by a C–Se coupling/cyclization reaction

• Pierre-Olivier Schwartz,
• Sebastian Förtsch,
• Astrid Vogt,
• Elena Mena-Osteritz and
• Peter Bäuerle

Beilstein J. Org. Chem. 2019, 15, 1379–1393, doi:10.3762/bjoc.15.138

• (Figure 2b), because a completely flat geometry of the isolated molecule DST 3 (in the gas phase) was obtained from theoretical calculations (vide infra). Molecules of DST 3 order in a typical herringbone fashion, where the terminal hydrogen atoms form hydrogen bond-like C–H heteroatom interactions (2.819

• signals at expected strong π–π intermolecular distances of 3.5–3.3 Å (2Θ = 25–26°), at offset π–π intermolecular distances of 4.1 Å (2Θ = 21.5°), and at herringbone intermolecular interaction distances of 8.2 Å (2Θ = 10.8°) were found and correlated with the Miller indices obtained in the X-ray single

• and fused selenophene rings. Single crystal X-ray structure analysis of selenolotriacene DST 3, (a) individual molecule and atom numbering (top view); (b) side view. (c) Herringbone-type packing structure of the four molecules in the unit. Single crystal X-ray structure analysis of selenolotriacene

Mechanochemical synthesis of thioureas, ureas and guanidines

• Vjekoslav Štrukil

Beilstein J. Org. Chem. 2017, 13, 1828–1849, doi:10.3762/bjoc.13.178

• stacks. In the structural family II, the characteristic (110) reflection is slightly shifted and appears at the Bragg diffraction angle range 8–10°. The infinite hydrogen-bonded chains are arranged in a herringbone pattern with an angle of 44° between neighbouring stacks (Figure 3). In the follow-up

Molecular recognition of N-acetyltryptophan enantiomers by β-cyclodextrin

• Spyros D. Chatziefthimiou,
• Mario Inclán,
• Petros Giastas,
• Athanasios Papakyriakou,
• Konstantina Yannakopoulou and
• Irene M. Mavridis

Beilstein J. Org. Chem. 2017, 13, 1572–1582, doi:10.3762/bjoc.13.157

• -CD [29]. This was an indication that the structure should be quite different from hydrated β-CD. However, no guest could be located during the refinement and the present structure (henceforth “β-CD–D-NAcTrp”) was refined as a β-CD–water complex (Table 2). “β-CD–D-NAcTrp” exhibits the “herringbone

Synthesis and properties of fluorescent 4′-azulenyl-functionalized 2,2′:6′,2″-terpyridines

• Adrian E. Ion,
• Liliana Cristian,
• Mariana Voicescu,
• Masroor Bangesh,
• Augustin M. Madalan,
• Daniela Bala,
• Constantin Mihailciuc and
• Simona Nica

Beilstein J. Org. Chem. 2016, 12, 1812–1825, doi:10.3762/bjoc.12.171

• exhibit a herringbone arrangement (Figure 2). This organization is sustained by CH–π interactions (H18∙∙∙centroid and H14′∙∙∙C10 contacts are 3.00 and 2.89 Å, respectively; symmetry code: ’ = −0.5 + x, −0.5 + y, 0.5 − z). Instead, the analysis of the packing diagrams in 4b (Figure 3) shows that only the

The chemical behavior of terminally tert-butylated polyolefins

• Dagmar Klein,
• Henning Hopf,
• Peter G. Jones,
• Ina Dix and
• Ralf Hänel

Beilstein J. Org. Chem. 2015, 11, 1246–1258, doi:10.3762/bjoc.11.139

• 12.2°). The molecular packing (Figure 2b) involves herringbone-type layers perpendicular to (). The shortest H…Br contacts of 3.05 Å, probably of only marginal significance, are formed between layers. Having unambiguously established that the mono adduct of bromine to pentaene 20 has the structure of a

TTFs nonsymmetrically fused with alkylthiophenic moieties

• Rafaela A. L. Silva,
• Bruno J. C. Vieira,
• Marta M. Andrade,
• Isabel C. Santos,
• Sandra Rabaça,
• Dulce Belo and
• Manuel Almeida

Beilstein J. Org. Chem. 2015, 11, 628–637, doi:10.3762/bjoc.11.71

• -chains, the molecules are connected by short S…S and S…O interactions with the tert-butyl groups pointing outside, in a herringbone fashion (Figure 3b). Molecules in different chains make an angle of circa 39° (Figure 3a). There are no close contacts between bi-chains (Figure 4). α-tbtdt (1) Compound 1

• dichloromethane versus Ag/AgNO3, with n-Bu4NPF6 (10−1 M) as supporting electrolyte. Scan rate ν = 100 mV/s at room temperature. ORTEP view and atomic numbering scheme of I with thermal ellipsoids at 50% probability level. Molecular herringbone bi-chains in the crystal structure of I: a) view along the molecular

Attempts to prepare an all-carbon indigoid system

• Şeref Yildizhan,
• Henning Hopf and
• Peter G. Jones

Beilstein J. Org. Chem. 2015, 11, 363–372, doi:10.3762/bjoc.11.42

• exhibits crystallographic inversion symmetry, but the true symmetry is close to C2h (rmsd 0.02 Å). The ring system is planar, with a mean deviation of only 0.02 Å. The molecular packing involves a herringbone pattern in layers perpendicular to the a-axis. There are no noticeably short intermolecular

• be obtained. The molecule 24 displays crystallographic inversion symmetry, although the true symmetry is close to C2h (rmsd 0.02 Å). The molecular packing involves herringbone layers, parallel to the bc plane, in which two C–H···π contacts to the centroid of the aromatic six-membered ring are

• is planar (mean deviation 0.02 Å), but the true symmetry is close to D2h (rmsd 0.02 Å). The central C=C bond length is 1.327(2) Å. The molecular packing involves herringbone layers, parallel to the plane (102), in which C-H···π contacts from a methylene hydrogen to the centroid of the six-membered

Anionic sigmatropic-electrocyclic-Chugaev cascades: accessing 12-aryl-5-(methylthiocarbonylthio)tetracenes and a related anthra[2,3-b]thiophene

• Laurence Burroughs,
• John Ritchie,
• Mkhethwa Ngwenya,
• Dilfaraz Khan,
• William Lewis and
• Simon Woodward

Beilstein J. Org. Chem. 2015, 11, 273–279, doi:10.3762/bjoc.11.31

• substituted tetracene 7j forms ribbons of herringbone structures. Estimates of the HOMO–LUMO data for 7 were taken from UV and CV measurements (see Table 3 and Supporting Information File 1), as well as by DFT calculations. Tetracenes 7d and 7f show the widest range in HOMO–LUMO perturbation while Eg opt. is

Inclusion of trans-resveratrol in methylated cyclodextrins: synthesis and solid-state structures

• Lee Trollope,
• Dyanne L. Cruickshank,
• Terence Noonan,
• Susan A. Bourne,
• Milena Sorrenti,
• Laura Catenacci and
• Mino R. Caira

Beilstein J. Org. Chem. 2014, 10, 3136–3151, doi:10.3762/bjoc.10.331

• as well as numerous water–water O–H···O hydrogen bonds. The crystal packing is shown in Figure 15. Complex units stack in columns parallel to the a-axis in a head-to-tail fashion with (as noted above) a small extent of host self-inclusion (Figure 15a). Figure 15b illustrates the modified herringbone

Preparation and evaluation of cyclodextrin polypseudorotaxane with PEGylated liposome as a sustained release drug carrier

• Kayoko Hayashida,
• Taishi Higashi,
• Daichi Kono,
• Keiichi Motoyama,
• Koki Wada and
• Hidetoshi Arima

Beilstein J. Org. Chem. 2014, 10, 2756–2764, doi:10.3762/bjoc.10.292

• useful for the confirmation of the PPRXs with CDs, as they provide enough information to distinguish between the herringbone packing of free CDs and the channel packing of inclusion complexes [13]. Therefore, the crystal structure of DOX/PEG-LP/γ-CD was determined by powder X-ray diffraction (Figure 3B

Molecular ordering at electrified interfaces: Template and potential effects

• Thanh Hai Phan and
• Klaus Wandelt

Beilstein J. Org. Chem. 2014, 10, 2243–2254, doi:10.3762/bjoc.10.233

• , or 14.49·1013 molecules/cm2. A more detailed discussion of the molecular arrangement within the herringbone rows is postponed until section Discussion where we will also make a comparison with the corresponding system DBV on Cl/Cu(100). The DBV-dication based herring-bone structure remains stable in

Scalable synthesis of 5,11-diethynylated indeno[1,2-b]fluorene-6,12-diones and exploration of their solid state packing

• Bradley D. Rose,
• Peter J. Santa Maria,
• Aaron G. Fix,
• Chris L. Vonnegut,
• Lev N. Zakharov,
• Sean R. Parkin and
• Michael M. Haley

Beilstein J. Org. Chem. 2014, 10, 2122–2130, doi:10.3762/bjoc.10.219

• molecules form 1-D π-stacks (interplanar spacing 3.446(5) Å) parallel to a, with adjacent stacks having the opposite tilt by virtue of the c-glide, leading to a herringbone motif in which inter-stack interactions are solely between the SiMe3 groups. This is the only structure of this type in the group of

• ten compounds. The next largest (8g, SiMe2PrF3, vol. ~198 Å3) is orthorhombic, Pca21, with a squat unit cell (short b axis). Molecules form 1-D π-stacks parallel to the b-axis (interplanar spacing 3.358(3) Å), while adjacent stacks interact via C-H···π contacts to form herringbone-patterned layers

• form 1-D π-stacks parallel to b (interplanar spacings of 3.454(2) Å, 3.340(2) Å and 3.385(3) Å, respectively, for 8b, 8i and 8h). Adjacent stacks along c interact via C–H···π-contacts, and are related by the c-glide operation to form the common herringbone motif (interstack molecular tilts of 64.88(2

Lateral ordering of PTCDA on the clean and the oxygen pre-covered Cu(100) surface investigated by scanning tunneling microscopy and low energy electron diffraction

• Stefan Gärtner,
• Benjamin Fiedler,
• Oliver Bauer,
• Antonela Marele and
• Moritz M. Sokolowski

Beilstein J. Org. Chem. 2014, 10, 2055–2064, doi:10.3762/bjoc.10.213

• phenomena is known for the adsorption of PTCDA on the reactive Ni(111) surface. In that case the interaction on the free surface is so strong that the molecules do not diffuse over the surface and hence do not form an ordered structure [23], whereas on p(2 × 2) – O/ /Ni(111) a well ordered herringbone

Aryl substitution of pentacenes

• Andreas R. Waterloo,
• Anna-Chiara Sale,
• Dan Lehnherr,
• Frank Hampel and
• Rik R. Tykwinski

Beilstein J. Org. Chem. 2014, 10, 1692–1705, doi:10.3762/bjoc.10.178

• incorporation of the ethynyl spacer in 2a–c provides for the lowest HOMO–LUMO gap of the molecules discussed here. X-ray crystallographic analysis Typically, three predominant solid-state packing patterns are found by X-ray crystallographic analysis of pentacene and its derivatives [13]: a) a herringbone

• packing, b) a one-dimensional (1D) slipped-stack, and c) a 2D “bricklayer” packing, as schematically summarized in Figure 4. While several polymorphs have been reported for unsubstituted pentacene [43][44][45][46], the arrangement in the solid state is commonly the edge-to-face, herringbone motif [47

• sandwich herringbone motif (Figure 5c) [50]. Each dimeric pair of pentacenes shows face-to-face π-stacking interactions with an interplanar distance of ~3.40 Å and a total overlap of nearly four of the aromatic pentacene rings. Pentacene 3b crystallizes in the space group P-1 with two molecules in the unit

Columnar/herringbone dual crystal packing of pyrenylsumanene and its photophysical properties

• Binod Babu Shrestha,
• Shuhei Higashibayashi and
• Hidehiro Sakurai

Beilstein J. Org. Chem. 2014, 10, 841–847, doi:10.3762/bjoc.10.80

• Science, Myodaiji, Okazaki, Aichi 444-8787, Japan, Japan Science and Technology Agency, ACT-C, 4-1-8 Honcho, Kawaguchi, Saitama 332-0012, Japan 10.3762/bjoc.10.80 Abstract A single crystal of pyrenylsumanene was found to exhibit both columnar and herringbone crystal packing. The sumanene moieties form

• unidirectional columnar structures based on π–π stacking while the pyrene moieties generate herringbone structures due to CH–π interactions. The absorption and emission maxima of pyrenylsumanene were both red-shifted relative to those of sumanene and pyrene, owing to the extension of π-conjugation. Monomer

• emission with high quantum yield (0.82) was observed for pyrenylsumanene in solution, while excimer-type red-shifted emission was evident in the crystalline phase. Keywords: carbon nanomaterials; columnar crystal packing; fluorescence; herringbone; pyrenylsumanene; Introduction Buckybowls – bowl-shaped

Crystal design using multipolar electrostatic interactions: A concept study for organic electronics

• Peer Kirsch,
• Qiong Tong and
• Harald Untenecker

Beilstein J. Org. Chem. 2013, 9, 2367–2373, doi:10.3762/bjoc.9.272

• colorless crystals, mp 302 °C. The solubility in THF-d8 and other suitable solvents was not sufficient for obtaining meaningful solution NMR spectra. MS (HPLC-APLI) m/z (%): 412 [M]+ (100). Schematic view of the different types of molecular arrangements in acene-based molecular semiconductors: "herringbone