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

• Shakeel Alvi Rashid Ali Department of Chemistry, Jamia Millia Islamia, Jamia Nagar, Okhla, New Delhi-110025, India, Phone: +91-7011867613 10.3762/bjoc.16.186 Abstract Since the first synthetic report in 2003 by Sakurai et al., sumanene (derived from the Indian ‘Hindi as well as Sanskrit word

• transfer systems, cation–π complexation, electron conductivity, optical properties and so on. Keeping the importance of this beautiful scaffold in mind, we compiled all the synthetic routes available for the construction of sumanene and its heteroatom derivatives including Mehta’s first unsuccessful effort

• up to the latest achievements. Our major goal to write this review article was to provide a quick summary of where the field has been, where it stands at present, and where it might be going in near future. Although several reviews have been published on sumanene chemistry dealing with different

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

• 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

• 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

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

• Science, Myodaiji, Okazaki, Aichi 444-8787, Japan, Japan Science and Technology Agency, ACT-C, 4-1-8 Honcho, Kawaguchi, Saitama 332-0012, Japan 10.3762/bjoc.10.80 Abstract A single crystal of pyrenylsumanene was found to exhibit both columnar and herringbone crystal packing. The sumanene moieties form

• unidirectional columnar structures based on π–π stacking while the pyrene moieties generate herringbone structures due to CH–π interactions. The absorption and emission maxima of pyrenylsumanene were both red-shifted relative to those of sumanene and pyrene, owing to the extension of π-conjugation. Monomer

• 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