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

• acids in the presence of Pd(PPh3)4 and K2CO3 in THF/water to furnish the required hexaarylated sumanenes in 20–85% yields (Scheme 23). In the same year, the groups of Hisaki, Sato and Sakurai have reported a hydrogen-bonded 2D sumanene buckybowl framework having 4,4’-dicarboxy-o-terphenyl groups in the

• valuable π-conjugated buckybowl. Four years later, McGlinchey’s group has tried to synthesize it by means of an organometallic precursor but they also did not make available the breakthrough for the research community [70][71]. On the other hand, four years before to the Mehta’s report, Klemm and co

Synthesis of C₇₀-fragment buckybowls bearing alkoxy substituents

• Yumi Yakiyama,
• Shota Hishikawa and
• Hidehiro Sakurai

Beilstein J. Org. Chem. 2020, 16, 681–690, doi:10.3762/bjoc.16.66

• equilibrium between the Pd(IV) intermediates through C–H bond activation. Keywords: buckybowl; C70; rearrangement through C–H bond activation; Introduction The study of buckybowls, the bowl-shaped π-conjugated aromatic hydrocarbons corresponding to the fragments of fullerenes, pioneered by the works on

• that with C60 fragment because most of them consists of acene and/or pyrene units, which might give unique photochemical and electrochemical properties. Recently, we synthesized a buckybowl C28H14 1, which is corresponding to a 40% fragment of C70, from C60-fragment sumanene (2) in three steps via ring

• the external aromatic ring of the indenopyrene using various types of o-bromo arylaldehydes. Related to our study on buckybowl-containing liquid crystals [19], we planned to introduce alkoxy groups on the 1 framework. Here, we report the synthesis and characterization of dimethoxy derivative 5a and

Recent applications of ring-rearrangement metathesis in organic synthesis

• Sambasivarao Kotha,
• Milind Meshram,
• Priti Khedkar,
• Shaibal Banerjee and
• Deepak Deodhar

Beilstein J. Org. Chem. 2015, 11, 1833–1864, doi:10.3762/bjoc.11.199

• required RRM product 208 was formed in 26% yield. Later, the expected chiral buckybowl 209 was assembled via aromatization of 208 in the presence of DDQ (Scheme 42). Design of intricate polyquinanes has been considered as a challenging task for synthetic chemists. To this end, Fallis and co-workers [46

Site-selective covalent functionalization at interior carbon atoms and on the rim of circumtrindene, a C₃₆H₁₂ open geodesic polyarene

• Hee Yeon Cho,
• Ronald B. M. Ansems and
• Lawrence T. Scott

Beilstein J. Org. Chem. 2014, 10, 956–968, doi:10.3762/bjoc.10.94

• reactions and to probe the magnetic environment of the concave/convex space around the hydrocarbon bowl. For both classes of functionalization, computational results are reported to complement the experimental observations. Keywords: Bingel–Hirsch reaction; buckybowl; carbon nanomaterials; cyclopropanation

• ’:8,9-b’’c’’d’’]trithiophene (5, C18H6S3) [18], the deep buckybowl circumtrindene (6, C36H12) [19][20], and even fullerene C60 (2) (Figure 1 and Figure 3) [21][22]. Syntheses of curved PAHs are not limited, however, to FVP; non-pyrolytic, “wet chemical” methods to access fullerene fragments have also

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

• favour a herringbone packing structure (Figure 1c) due to π–π and CH–π interactions [19][20]. To date, buckybowl derivatives with planar aromatic substituents have not been well studied and thus we wished to examine the crystal packing modes and solid-state properties of dual-nature compounds

• columnar structure of buckybowl crystals resulting from convex–concave intermolecular π–π interactions is expected to be quite predictable and to serve as a directing force to provide specific crystal structures [16][17]. The present study demonstrates the promising possibility of utilizing the sumanene