Accessing extended and partially fused hexabenzocoronenes using a benzannulation–cyclodehydrogenation approach

Hasan Arslan, Fernando J. Uribe-Romo, Brian J. Smith, William R. Dichtel*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

52 Scopus citations

Abstract

A rapid and efficient approach to prepare extended or partially fused hexabenzocoronene derivatives is described. The method is based on the sequential benzannulation and cyclodehydrogenation (Scholl oxidation) of simple diaryl alkynes. The benzannulation reaction proceeds efficiently on highly congested substrates and with complete regioselectivity. Scholl oxidation of the resulting oligo(arylene)s proceeds without rearrangements and provides either fully fused or specific partially fused polycyclic aromatic hydrocarbon products. The partially fused derivatives are a new class of contorted aromatic systems with high solubility, enhanced visible absorption, and reversible redox processes. The efficiency and specificity of the benzannulation and oxidation reactions are promising for accessing new classes of organic semiconductors and carbon nanostructures.

Original languageEnglish (US)
Pages (from-to)3973-3978
Number of pages6
JournalChemical Science
Volume4
Issue number10
DOIs
StatePublished - Aug 26 2013

ASJC Scopus subject areas

  • Chemistry(all)

Fingerprint Dive into the research topics of 'Accessing extended and partially fused hexabenzocoronenes using a benzannulation–cyclodehydrogenation approach'. Together they form a unique fingerprint.

Cite this