2021
DOI: 10.1002/anie.202112589
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Five‐Fold Symmetric Pentaindolo‐ and Pentakis(benzoindolo)Corannulenes: Unique Structural Dynamics Derived from the Combination of Helical and Bowl Inversions

Abstract: Peripherally p-extended corannulenes bearing quintuple azahelicene units, 10 and 11,w ere prepared and their dynamic behaviors were studied experimentally and theoretically.T he fused corannulenes were synthesized from sympentabromocorannulene in three steps.X -Rayd iffraction analysis for 10 displayed aconformer possessing aP(M) bowl chirality and aP PMPM (PMPMM) helical chirality,w hich was found to be the most stable conformer(s). Variabletemperature NMR measurements of 10 and 11 revealed that their structu… Show more

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Cited by 22 publications
(6 citation statements)
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“…In their solid states, the unit cell of 1 a‐1 contains two enantiomers with helical chirality ( M : green color; P : orange color) and they pack into an ordered head‐to‐tail columnar arrangement along the c ‐axis, where the distances between two enantiomers are in the range of 3.41 to 3.67 Å (Figure 3d). Interestingly, 1 a‐2 displays unique bowl chirality due to its reflection asymmetric feature and the steric repulsion caused by the substituents along the zigzag edges [29–32] . To the best of our knowledge, this is the first example of tricoordinate B‐doped polycyclic aromatic hydrocarbons (PAHs) with bowl chirality (Figure 3e).…”
Section: Figurementioning
confidence: 98%
See 1 more Smart Citation
“…In their solid states, the unit cell of 1 a‐1 contains two enantiomers with helical chirality ( M : green color; P : orange color) and they pack into an ordered head‐to‐tail columnar arrangement along the c ‐axis, where the distances between two enantiomers are in the range of 3.41 to 3.67 Å (Figure 3d). Interestingly, 1 a‐2 displays unique bowl chirality due to its reflection asymmetric feature and the steric repulsion caused by the substituents along the zigzag edges [29–32] . To the best of our knowledge, this is the first example of tricoordinate B‐doped polycyclic aromatic hydrocarbons (PAHs) with bowl chirality (Figure 3e).…”
Section: Figurementioning
confidence: 98%
“…Interestingly, 1 a-2 displays unique bowl chirality due to its reflection asymmetric feature and the steric repulsion caused by the substituents along the zigzag edges. [29][30][31][32] To the best of our knowledge, this is the first example of tricoordinate B-doped polycyclic aromatic hydrocarbons (PAHs) with bowl chirality (Figure 3e). In the crystal packing, two enantiomers (M and P) of 1 a-2 form the face-to-face π-stacked dimer structure in its unit cell with a distance of 3.24 Å, and the unit cell is further arranged into an ordered columnar superstructure.…”
mentioning
confidence: 99%
“…As shown in Fig. 15, Tanaka et al 42 synthesized two nitrogen-doped quintuple helicenes, 42 and 43 , in three key steps. Firstly, a five-fold Buchwald–Hartwig reaction between pentabromocorannulene and aromatic amines afforded precursors 40 and 41 .…”
Section: Multiple Helicenes With Corannulene As the Corementioning
confidence: 99%
“…The most commonly found examples are those with nitrogen atoms at the peripheral positions or within the polycyclic skeleton (Figure ). …”
Section: Introductionmentioning
confidence: 99%