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

• in materials science and technology. Keywords: buckybowls; heterosumanenes; polyaromatic hydrocarbons; sumanene; synthesis; Review 1 Introduction Over a long period of time, polyaromatic hydrocarbons (PAHs) have attracted a tremendous attention of the scientific community because of their diverse

• et al. [13], this field of research is continuously booming because of the developments of advanced synthetic organic tools [14][15][16]. Among the PAHs, the buckybowls are of significant importance not only because of the presence of unique inherent chirality (bowl-chirality) originating either from

• a tendency of crystal packing [17][18][19][20]. Since these chiral buckybowls contain stable convex or concave faces suitable for the generation of chiral molecular recognition sites which can be used for the construction of helical assemblies and have been used to coordinate the metal atom(s) [21

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

• Yumi Yakiyama Shota Hishikawa Hidehiro Sakurai Division of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan 10.3762/bjoc.16.66 Abstract Buckybowls bearing a C70 fragment having two alkoxy groups were synthesized and their structural

• 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

• colannulene and sumanene, have been attracting great interests owing to their unique chemical and physical properties [1][2][3][4][5][6][7][8] and was extended to larger systems [9][10][11][12][13][14][15][16][17]. Among them, buckybowls having a C70 fragment are expected to exhibit different properties from

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

• many examples of covalent chemistry for fullerenes (i.e., closed geodesic polyarenes), covalent functionalizations of open geodesic polyarenes other than corannulene have been reported only rarely. As in fullerene chemistry, chemical derivatization of buckybowls can be expected to change the electronic

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

• emission with high quantum yield (0.82) was observed for pyrenylsumanene in solution, while excimer-type red-shifted emission was evident in the crystalline phase. Keywords: carbon nanomaterials; columnar crystal packing; fluorescence; herringbone; pyrenylsumanene; Introduction Buckybowls – bowl-shaped

• aromatic hydrocarbons – possess unique physical properties due to their curved π-conjugated systems [1][2][3][4][5]. One of these characteristic features is a columnar packing structure in the crystal state. Many buckybowls, including sumanene [2], exhibit columnar packing in which the bowl-shaped

• molecules are stacked in a convex-to-concave fashion, since this particular pattern results in more highly favored intermolecular π–π interactions [1][2][3][4][5][6][7][8][9][10][11][12][13]. The columnar packing structures of buckybowls typically occur in two forms which are differentiated by the stacking