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Synfacts 2014; 10(6): 0581
DOI: 10.1055/s-0033-1339044
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

Efficient Three-Fold Symmetrical Nanographene Synthesis

Contributor(s):
Timothy M. Swager
,
Byungjin Koo
Zhang Q, Peng H, Zhang G, Lu Q, Chang J, Dong Y, Shi X, Wei J * Shaanxi Normal University, Xi’an, P. R. of China
Facile Bottom-Up Synthesis of Coronene-based 3-Fold Symmetrical and Highly Substituted Nanographenes from Simple Aromatics.

J. Am. Chem. Soc. 2014;
136: 5057-5064
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Further Information

Publication History

Publication Date:
16 May 2014 (online)

 
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Key words

nanographenes - Friedel–Crafts reaction - Scholl reaction

Significance

An efficient synthesis of nanographenes is reported. The key is recognizing that hexa-cata-hexabenzocoronene (c-HBC) possesses three-fold symmetry and that only seven of the 13 benzene rings are enough to build up c-HBC. 2 reacts with three equivalents of an aromatic aldehyde via Friedel–Crafts and Scholl reaction.


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Comment

Alkoxy groups for R1 and R2 were employed to generate electron-rich compound 2 which is more reactive towards Friedel–Crafts and Scholl reaction. Bromo-substituted (R3) c-HBC can be potentially utilized to prepare more functionalized nanographenes.


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