A Large Starphene Comprising Pentacene Branches

Holec, Jan; Cogliati, Beatrice; Lawrence, James; Berdonces‐Layunta, Alejandro; Herrero, Pablo; Nagata, Yuuya; Banasiewicz, Marzena; Kozankiewicz, Β.; Corso, Martina; Oteyza, Dimas G. de; Jančařík, Andrej; Gourdon, André

doi:10.1002/ange.202016163

Cited by 9 publications

(7 citation statements)

References 41 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The same may be concluded from the close to zero NICS(1) value on that ring (Figure 4g). Such NICS(1) value reflects the single-bond character of the connection between the acene units 20 and consequently (with the associated phenyl rings) the radialene character 52 that causes the conjugation between the two pentacene monomers to be weak. 24…”

Section: ■ Discussionmentioning

confidence: 99%

“…In a continuous search for increasingly complex structures, such molecules have been further combined into oligomers or polymers, − evidencing an impressively rich phenomenology and varying properties with a strong dependence on the coupling motifs. Scheme a illustrates anthracenes , and tetracenes ,, coupled at C2 and C3 positions, forming dimers fused through a non-benzenoid cyclobutadiene ring in a straight linear motif (see Scheme S1a for numbering guide on acene).…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Tuning the Diradical Character of Pentacene Derivatives via Non-Benzenoid Coupling Motifs

et al. 2023

Self Cite

View full text Add to dashboard Cite

The development of functional organic molecules requires structures of increasing size and complexity, which are typically obtained by the covalent coupling of smaller building blocks. Herein, with the aid of high-resolution scanning tunneling microscopy/spectroscopy and density functional theory, the coupling of a sterically demanded pentacene derivative on Au(111) into fused dimers connected by non-benzenoid rings was studied. The diradical character of the products was tuned according to the coupling section. In particular, the antiaromaticity of cyclobutadiene as the coupling motif and its position within the structure play a decisive role in shifting the natural orbital occupancies toward a stronger diradical electronic character. Understanding these structure–property relations is desirable not only for fundamental reasons but also for designing new complex and functional molecular structures.

show abstract

Section: ■ Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Tuning the Diradical Character of Pentacene Derivatives via Non-Benzenoid Coupling Motifs

et al. 2023

Self Cite

View full text Add to dashboard Cite

show abstract

“…For this reason, we propose a COF that is based on the recently reported class of Starphene molecules which are triangular molecules of fused benzene rings. 48 When connected, a highly porous COF with a honeycomb lattice would result which we call Starphene-COF, as shown in Fig. 4 a and b.…”

Section: Towards a Measurable Hb In 2d Cofsmentioning

confidence: 99%

Hierarchies of Hofstadter butterflies in 2D covalent-organic frameworks

Bodesheim¹,

Biele²,

Cuniberti³

2022

Preprint

View full text Add to dashboard Cite

The Hofstadter butterfly is one of the first and most fascinating examples of the fractal and selfsimilar quantum nature of free electrons in a lattice pierced by a perpendicular magnetic field. However, the direct experimental verification of this effect on single-layer materials is still missing as very strong and inaccessible magnetic fields are necessary. For this reason, its indirect experimental verification has only been realized in artificial periodic 2D systems, like moiré lattices. The only recently synthesized 2D covalent-organic frameworks might circumvent this limitation: Due to their large pore structures, magnetic fields needed to detect most features of the Hofstadter butterfly are indeed accessible with today technology. This work opens the door to make this exotic and theoretical issue from the 70s measurable and might solve the quest for the experimental verification of the Hofstadter butterfly in single-layer materials. Moreover, the intrinsic hierarchy of different pore sizes in 2D covalent-organic framework adds additional complexity and beauty to the original butterflies and leads to a direct accessible playground for new physical observations.

show abstract

“…Since Kobayashi‐type aryne precursors are readily available, palladium‐catalyzed trimerizations were used for the synthesis of larger PAHs, e.g. based on napthalenes [20] phenanthrenes [20a, 21] triphenylenes [22] corannulene [23] biphenylene, [24] benzoperylene, [25] dibenzoanthracene, [26] tetracenediones, [27] indole regioisomers [28] or ketal protected pentaceneprecursors [29] . An impressive example is the reaction of didehydro[5]helicene derived from the corresponding ortho ‐(trimethylsilyl)phenyl‐triflate leading to a hexapole helicene, [30] which was successfully converted to a planar nanographene with 22 annulated rings on an Au(111)‐surface and was investigated by AFM and STM methods [31] …”

Section: Introductionmentioning

confidence: 99%

Palladium‐Catalyzed Cyclization of a Pyryne Precursor to Higher Pyrenylenes

et al. 2023

View full text Add to dashboard Cite

The palladium catalyzed cyclotrimerization of ortho-silylaryl triflates as aryne precursors is meanwhile an established method to synthesize polycyclic aromatic hydrocarbons (PAHs) with triphenylene cores. During the palladium-catalyzed reaction of a pyrene with an osilylaryl triflate moiety in the K-region higher homologues with central eight-and ten-membered rings (the pyrenylenes) were found, besides the expected trimer and a protocol was developed to isolate all members of this series. This unprecedented new class of PAHs was fully investigated by all means, including X-ray diffraction of single-crystals, UV/Vis and fluorescence spectroscopy and theoretical calculations. Supported by density-functional theory (DFT) calculations, a mechanism of all higher cyclooligomers is proposed.

show abstract

A Large Starphene Comprising Pentacene Branches

Cited by 9 publications

References 41 publications

Tuning the Diradical Character of Pentacene Derivatives via Non-Benzenoid Coupling Motifs

Tuning the Diradical Character of Pentacene Derivatives via Non-Benzenoid Coupling Motifs

Hierarchies of Hofstadter butterflies in 2D covalent-organic frameworks

Palladium‐Catalyzed Cyclization of a Pyryne Precursor to Higher Pyrenylenes

Contact Info

Product

Resources

About