Diazatetracenes Derived from the Benzannulation of Acetylenes: Electronic Tuning via Substituent Effects and External Stimuli

Dan Lehnherr, Joaquin M. Alzola, Catherine R. Mulzer, Samuel J. Hein, William R. Dichtel*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

13 Scopus citations

Abstract

Functionalized diazatetracenes are prepared using a new two-step sequence. The use of a dichlorobenzaldehyde in a Cu-catalyzed benzannulation of acetylenes provides functionalized dichloronaphthalenes that afford diazatetracenes using Buchwald-Hartwig aminations. This approach provides unique substitution patterns and rapid access to covalently linked dimeric diazatetracenes. Their electronic properties are characterized by UV-vis absorption/emission and cyclic voltammetry, revealing strong effects from both external stimuli by acid and internal substituent effects.

Original languageEnglish (US)
Pages (from-to)2004-2010
Number of pages7
JournalJournal of Organic Chemistry
Volume82
Issue number4
DOIs
StatePublished - Feb 17 2017

ASJC Scopus subject areas

  • Organic Chemistry

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