Nanopatterns of arylene–alkynylene squares on graphite: self-sorting and intercalation

• Tristan J. Keller,
• Joshua Bahr,
• Kristin Gratzfeld,
• Nina Schönfelder,
• Marcin A. Majewski,
• Marcin Stępień,
• Sigurd Höger and
• Stefan-S. Jester

Beilstein J. Org. Chem. 2019, 15, 1848–1855, doi:10.3762/bjoc.15.180

• the solubility limit can be overcome by appropriate substitution. We recently investigated self-assembled nanoporous networks of shape-persistent macrocycles in which dithiophene-based corner building blocks connect linear oligo(phenylene–ethynylene–butadiynylene)s (OPEBs) to form molecular polygons

Olefin metathesis in multiblock copolymer synthesis

• Maria L. Gringolts,
• Yulia I. Denisova,
• Eugene Sh. Finkelshtein and
• Yaroslav V. Kudryavtsev

Beilstein J. Org. Chem. 2019, 15, 218–235, doi:10.3762/bjoc.15.21

• functionalized with N-hydroxysuccinate esters (NHS) that can be used as a carrier for antitumor drugs, and the C block is a far-red emitting conjugated random copolymer of p-phenylene ethynylene (PPE) and perylene monoimide (PMI, Figure 2). For the synthesis, the random PPE–PMI copolymer was end-capped with

Interactions between shape-persistent macromolecules as probed by AFM

• Johanna Blass,
• Jessica Brunke,
• Franziska Emmerich,
• Cédric Przybylski,
• Vasil M. Garamus,
• Artem Feoktystov,
• Roland Bennewitz,
• Gerhard Wenz and
• Marcel Albrecht

Beilstein J. Org. Chem. 2017, 13, 938–951, doi:10.3762/bjoc.13.95

• polymers have been reported so far, including CD-modified conjugated oligomers and polymers composed of rigid phenylene ethynylene (PPE) structure units which are able to form self-inclusion complexes with tunable electrochemical properties [29][30][31][32][33][34][35]. The synthesis of PPE, in which two β

Learning from the unexpected in life and DNA self-assembly

• Jennifer M. Heemstra

Beilstein J. Org. Chem. 2015, 11, 2713–2720, doi:10.3762/bjoc.11.292

• at the University of Illinois describing their pioneering work on helical phenylene ethynylene foldamers. As with many things in my scientific career, I was drawn to this work because it was “just so cool.” While I was still an undergrad, James offered to introduce me to Jeff by email, and this

Supramolecular chemistry: from aromatic foldamers to solution-phase supramolecular organic frameworks

• Zhan-Ting Li

Beilstein J. Org. Chem. 2015, 11, 2057–2071, doi:10.3762/bjoc.11.222

• structures was to explore their potential functions as acyclic receptors. Moore et al. had utilized this approach to investigate the binding of m-phenylene ethynylene foldamers for nonpolar organic molecules in polar media [44]. All the C=O oxygen atoms of 21 point into the cavity of the helix, which has a

Single-molecule conductance of a chemically modified, π-extended tetrathiafulvalene and its charge-transfer complex with F₄TCNQ

• Raúl García,
• M. Ángeles Herranz,
• Edmund Leary,
• M. Teresa González,
• Gabino Rubio Bollinger,
• Marius Bürkle,
• Linda A. Zotti,
• Yoshihiro Asai,
• Fabian Pauly,
• Juan Carlos Cuevas,
• Nicolás Agraït and
• Nazario Martín

Beilstein J. Org. Chem. 2015, 11, 1068–1078, doi:10.3762/bjoc.11.120

• similar to the oxidation peak found for pristine exTTF (Epa = 244 mV, ΔE = 350 mV) (Figure 2). Break junction measurements Neutral molecule We first tried to form neutral-molecule molecular junctions. Simply, compound 5 can be seen as an analogue of an oligo(phenylene ethynylene), specifically an OPE3

Synthesis and chemosensing properties of cinnoline-containing poly(arylene ethynylene)s

• Natalia A. Danilkina,
• Petr S. Vlasov,
• Semen M. Vodianik,
• Andrey A. Kruchinin,
• Yuri G. Vlasov and
• Irina A. Balova

Beilstein J. Org. Chem. 2015, 11, 373–384, doi:10.3762/bjoc.11.43

• exciton are spatially separated, the quenching amplification factor is only limited by the diffusion distance of the exciton. In practice, a single bound analyte molecule can deactivate excitons within 130 neighboring phenylene ethynylene repeating units [4]. Sensors based on CPs can be classified either

• by the nature of the polymer backbone, e.g., polyphenylenes, polythiophenes, poly(phenylene vinylene)s, poly(phenylene ethynylene)s etc, or by their chemosensing properties [3][4]. The latter depends on the nature of receptors (recognizing units) incorporated into a polymer chain that bind an analyte

Mono- and multilayers of molecular spoked carbazole wheels on graphite

• Stefan-S. Jester,
• A. Vikas Aggarwal,
• Daniel Kalle and
• Sigurd Höger

Beilstein J. Org. Chem. 2014, 10, 2783–2788, doi:10.3762/bjoc.10.295

• resulting molecule–surface interaction decrease the ability to form a regular pattern, probably (also) due to a lower compound solubility. We observed a similar behavior for phenylene–ethynylene–butadiynylene macrocycles which we compared to their acyclic analoga of identical oligomerization degree [7

The influence of intraannular templates on the liquid crystallinity of shape-persistent macrocycles

• Joscha Vollmeyer,
• Ute Baumeister and
• Sigurd Höger

Beilstein J. Org. Chem. 2014, 10, 910–920, doi:10.3762/bjoc.10.89

• 4, 06120 Halle (Saale), Germany 10.3762/bjoc.10.89 Abstract A series of shape-persistent phenylene–ethynylene–naphthylene–butadiynylene macrocycles with different extraannular alkyl groups and intraannular bridges is synthesized by oxidative Glaser-coupling of the appropriate precursors. The

• molecule’s ability to form liquid crystalline phases. The macrocycles are based on a phenylene–ethynylene–naphthylene–butadiynylene backbone. Naphthylene units at the four corners are expected to have a higher mesomorphic tendency compared with compounds solely based on phenylene units [46]. Moreover, the

Efficient synthesis of phenylene-ethynylene rods and their use as rigid spacers in divalent inhibitors

• Francesca Pertici,
• Norbert Varga,
• Arnoud van Duijn,
• Matias Rey-Carrizo,
• Anna Bernardi and
• Roland J. Pieters

Beilstein J. Org. Chem. 2013, 9, 215–222, doi:10.3762/bjoc.9.25

• , Universita’ degli Studi di Milano, via Golgi 19, 20133 Milano, Italy 10.3762/bjoc.9.25 Abstract The synthesis of phenylene-ethynylene rods and their use as rigid spacers is described. Alternation of a Sonogashira reaction and silyl group cleavage was used to obtain rigid spacers with even and odd numbers of

• phenylene units. Preliminary applications of these rods in divalent systems are shown. Inhibition studies with Pseudomonas Aeruginosa lectin LecA showed that the rigid spacer proved greatly beneficial for the inhibitory potency. Keywords: multivalent carbohydrates; LecA inhibition; phenylene ethynylene

• units the phenylene-ethynylene unit has seen considerable interest in sensor [16] and molecular-electronics applications [17]. This is due to the specific fluorescent, conducting and electrochemical properties that the conjugated system confers to the molecule [18]. In the study of carbohydrate–protein

Miniemulsion polymerization as a versatile tool for the synthesis of functionalized polymers

• Daniel Crespy and
• Katharina Landfester

Beilstein J. Org. Chem. 2010, 6, 1132–1148, doi:10.3762/bjoc.6.130

• . Coupling reactions Pd-catalyzed cross-coupling reactions were carried out in direct aqueous miniemulsions with 1,2,4-tribromobenzene as crosslinker [132]. Aqueous latexes of crosslinked poly(p-phenylene ethynylene) were obtained and their opto-electronic properties were found to be similar to the linear

Low temperature enantiotropic nematic phases from V-shaped, shape-persistent molecules

• Matthias Lehmann and
• Jens Seltmann

Beilstein J. Org. Chem. 2009, 5, No. 73, doi:10.3762/bjoc.5.73

• Matthias Lehmann Jens Seltmann Institute of Chemistry, Chemnitz University of Technology, Straße der Nationen 62, 09111 Chemnitz, Germany 10.3762/bjoc.5.73 Abstract A series of V-shaped, shape-persistent thiadiazole nematogens, based on an oligo(phenylene ethynylene) scaffold with ester groups

• design a shape-persistent molecular scaffold of type I (Figure 2) based on oligo(phenylene ethynylene) building blocks. These molecules show liquid crystal behaviour only with a flat bending unit possessing a dipole along the apex of the mesogen, sufficiently long aliphatic chains R and at least one

• in Table 1. Interestingly, all phenylene ethynylene oligomers show exclusively enantiotropic nematic liquid crystal phases, even for the hockey stick shaped intermediates 3. However, the temperature intervals for the latter are small, approaching a maximum of 43 °C for compound 3c and melting in all

Shape- persistent macrocycle with intraannular alkyl groups: some structural limits of discotic liquid crystals with an inverted structure

• Sigurd Höger,
• Jill Weber,
• Andreas Leppert and
• Volker Enkelmann

Beilstein J. Org. Chem. 2008, 4, No. 1, doi:10.1186/1860-5397-4-1

• ][22]. Recently, we could show that shape-persistent macrocycles with fixed intraannular side chains (e.g. 1) can also exhibit liquid crystalline behavior [23][24]. Compound 1 is a shape-persistent macrocycle which is based on the phenylene-ethynylene-butadiynylene backbone. As it generally holds for