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

Wang XY, Narita A, Zhang W, Feng X, Muellen K (2016)

Publication Type: Journal article

Publication year: 2016

Journal

Journal of the American Chemical Society American Chemical Society

Book Volume: 138

Pages Range: 9021-9024

Journal Issue: 29

DOI: 10.1021/jacs.6b04092

Abstract

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.

Involved external institutions

Max-Planck-Institut für Polymerforschung (MPI-P) / Max Planck Institute for Polymer Research DE Germany (DE) Technische Universität Dresden DE Germany (DE)

How to cite

APA:

Wang, X.-Y., Narita, A., Zhang, W., Feng, X., & Muellen, K. (2016). Synthesis of Stable Nanographenes with OBO-Doped Zigzag Edges Based on Tandem Demethylation-Electrophilic Borylation. Journal of the American Chemical Society, 138(29), 9021-9024. https://doi.org/10.1021/jacs.6b04092

MLA:

Wang, Xiao-Ye, et al. "Synthesis of Stable Nanographenes with OBO-Doped Zigzag Edges Based on Tandem Demethylation-Electrophilic Borylation." Journal of the American Chemical Society 138.29 (2016): 9021-9024.

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