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Synthesis of Stable Nanographenes with OBO-Doped Zigzag Edges Based on Tandem Demethylation-Electrophilic Borylation

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journal contribution
posted on 04.07.2016, 00:00 authored by Xiao-Ye Wang, Akimitsu Narita, Wen Zhang, Xinliang Feng, Klaus Müllen
A tandem demethylation-aryl borylation strategy was developed to synthesize OBO-doped tetrabenzo­[a,f,j,o]­perylenes (namely “bistetracenes”) and tetrabenzo­[bc,ef,kl,no]­coronenes (namely “peritetracenes”). The OBO-doped bistetracene analogues exhibited excellent stability and strong fluorescence, in contrast to the unstable all-carbon bistetracene. Single-crystal X-ray analysis for OBO-doped bistetracene revealed a twisted double [5]­helicene structure, indicating that this synthesis is applicable to new heterohelicenes. Importantly, cyclodehydrogenation of the bistetracene analogues successfully produced the unprecedented heteroatom-doped peritetracenes, which opened up a new avenue to periacene-type nanographenes with stable zigzag edges.