Synthesis and Conformational Analysis of 10-Mesitylanthracene-1,8-diyl Oligomers

Toyota, Shinji; Saibara, Toyoaki; Fujise, Kei; Oki, Tomohiro; Iwanaga, Takeshi

doi:10.1055/s-0037-1609869

Cited by 6 publications

(1 citation statement)

References 8 publications

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“…The analysis gave the rate of enantiomerization at 5.7×10 −6 s −1 at 40 °C corresponding to the activation free energy of Δ G ≠ 298 108 kJ mol −1 (Figure S17). This barrier was higher than those of Nap 2 (98 kJ mol −1 ) [3] and 1,1′‐ Ant 2 (96 kJ mol −1 ) [8f,g] . These data indicated that the barriers were slightly enhanced by the fusion of additional aromatic moieties relative to Ant 2 .…”

Section: Resultsmentioning

confidence: 77%

Structure and Chiroptical Properties of Anthra[1,2‐a]anthracene‐1‐yl Dimers as New Biaryls

Watanabe,

Tsurumaki,

Hasegawa

et al. 2024

Chemistry A European J

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Dimers of anthra[1,2‐a]anthracene‐1‐yl units and its mesityl derivative were synthesized by Ni(0)‐mediated coupling of the corresponding chloro derivatives as new biaryls. The X‐ray analysis and DFT calculations revealed that two polycyclic aromatic units with nonplanar deformations took a twisted conformation about the single bond as a chiral axis. Enantiomers of the nonsubstituted compound were resolved by chiral HPLC, and the enantiopure samples showed intense Cotton effects at 321 nm in the circular dichroism (CD) spectra and emission bands at 449 nm in the circularly polarized luminescence (CPL) spectra with dissymmetry factor of |glum| 3.6 × 10–3. The absolute stereochemistry of this biaryl was determined by the theoretical calculation of CD spectrum by the time‐dependent DFT method. The barrier to enantiomerization was determined to be 108 kJ mol–1 at 298 K. The dynamic process proceeded via a stepwise mechanism involving the helical inversion of each aromatic unit and the rotation about the biaryl axis as analyzed by the DFT calculations.

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Section: Resultsmentioning

confidence: 77%

Structure and Chiroptical Properties of Anthra[1,2‐a]anthracene‐1‐yl Dimers as New Biaryls

Watanabe,

Tsurumaki,

Hasegawa

et al. 2024

Chemistry A European J

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Chemistry of Anthracene−Acetylene Oligomers XXVII. Iterative Synthesis, Structures, and Properties of Anthracene−Diacetylene Cyclic Oligomers with 10‐Mesitylanthracene‐1,8‐diyl Units

et al. 2018

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A series of cyclic oligomers consisting of 10‐mesitylanthracene‐1,8‐diyl units and diacetylene linkers were synthesized as soluble π‐conjugated compounds. Macrocyclic frameworks from dimer to octamer except heptamer were constructed from 1,8‐diethynylanthracene derivatives by iterative coupling reactions. The rigid structure of the dimer, the strained structures of the trimer and the pentamer, and the belt‐shaped structures of the other even‐numbered oligomers were revealed by X‐ray analysis and DFT calculations. The dynamic behavior of the cyclic oligomers was analyzed by observing variable‐temperature 1H NMR spectra. The UV/Vis and fluorescence spectra of these emissive cyclic compounds are discussed on the basis of the molecular structures.

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Complexation of an Anthracene‐Triptycene Nanocage Host with Fullerene Guests through CH⋅⋅⋅π Contacts

et al. 2021

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A bicyclic anthracene macrocycle containing two triptycene units at the bridgehead positions was synthesized by Nimediated coupling of the corresponding precursor as a cageshaped aromatic hydrocarbon host. This cage host formed an inclusion complex with C 60 or C 70 guest in 1 : 1 ratio in solution. The association constants (K a ) determined by the fluorescence titration method were 1.3 × 10 4 and 3.3 × 10 5 L mol À 1 for the C 60 and C 70 complexes, respectively, at 298 K in toluene. DFT calculations revealed that the guest molecules were included in the middle of the cavity with several CH•••π contacts. The strong affinity of the cage host for the fullerene guests and the high selectivity toward C 70 are discussed on the basis of spectroscopic and structural data.

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Synthesis and Conformational Analysis of 10-Mesitylanthracene-1,8-diyl Oligomers

Cited by 6 publications

References 8 publications

Structure and Chiroptical Properties of Anthra[1,2‐a]anthracene‐1‐yl Dimers as New Biaryls

Structure and Chiroptical Properties of Anthra[1,2‐a]anthracene‐1‐yl Dimers as New Biaryls

Chemistry of Anthracene−Acetylene Oligomers XXVII. Iterative Synthesis, Structures, and Properties of Anthracene−Diacetylene Cyclic Oligomers with 10‐Mesitylanthracene‐1,8‐diyl Units

Complexation of an Anthracene‐Triptycene Nanocage Host with Fullerene Guests through CH⋅⋅⋅π Contacts

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