Beilstein J. Org. Chem.2020,16, 2212–2259, doi:10.3762/bjoc.16.186
the pyrene moiety, an appealing sumanene derivative 93, namely as pyrenylsumanene, was constructed by the groups of Higashibayashi and Sakurai which display both herringbone and columnar crystal packing (Scheme 22) [53]. To synthesize this architecturally interesting molecule, they began with the
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Figure 1:
Representation of corannulene (1) and sumanene (2), the subunits of fullerene (C60).
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
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
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Graphical Abstract
Figure 1:
Columnar packing structures of buckybowls showing (a) unidirectional and (b) opposite structures, i...